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NLM database Documents
Record 1 from database: MEDLINE
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- Title
- Metabolism of dimethyl sulfide, dimethyl sulfoxide, and
dimethyl sulfone in the rabbit.
- Author
- Williams KI; Burstein SH; Layne DS
- Address
-
- Source
- Arch Biochem Biophys, 1966 Oct, 117:1, 84-7
- Abstract
- Abstract unavailable online.
- Language of Publication
- English
- Unique Identifier
- 67181631
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- MeSH Heading (Major)
- Dimethyl Sulfoxide|*ME; Sulfides|*ME; Sulfones|*UR
- MeSH Heading
- Animal; Carbon Isotopes; Chromatography, Gas; Rabbits
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0003-9861
- Country of Publication
- UNITED STATES
Record 2 from database: MEDLINE
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- Title
- A new method for assay of radioactive dimethyl sulfoxide
and its metabolite, dimethyl sulfone.
- Author
- Hucker HB; Hoffman EA
- Address
-
- Source
- Experientia, 1966 Dec, 22:12, 855-6
- Abstract
- Abstract unavailable online.
- Language of Publication
- English
- Unique Identifier
- 67202189
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- MeSH Heading (Major)
- Dimethyl Sulfoxide|*AN; Sulfones|*AN
- MeSH Heading
- Animal; Chlorides; Rats; Sulfur Isotopes; Tin
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0014-4754
- Country of Publication
- SWITZERLAND
Record 3 from database: MEDLINE
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- Title
- [Effect of dimethyl sulfoxide and dimethyl sulfone on a
destructive process in the joints of mice with spontaneous
arthritis]
- Author
- Muravev IuV; Venikova MS; Pleskovskaia GN; Riazantseva TA;
Sigidin IaA
- Address
-
- Source
- Patol Fiziol Eksp Ter, 1991 Mar, :2, 37-9
- Abstract
- The authors used the blind method for evaluation of the
morphological picture of the joints and the level of
circulating immune complexes to study the effect of
prolonged oral administration of dimethyl sulfoxide (DMSO)
and its main metabolite dimethyl sulfone on the development
of spontaneous arthritis in 36 Mrl/Mn/lnr female mice. It
was found that DMSO and dimethyl sulfone lessen the
destructive changes in the joints, while DMSO also inhibits
the manifestation of immune disorders, i. e. produces a
"basal" effect on the course of spontaneous
chronic arthritis in experimental animals.
- Language of Publication
- Russian
- Unique Identifier
- 91351749
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- MeSH Heading (Major)
- Arthritis|*DT/ET/PA; Dimethyl Sulfoxide|*TU; Sulfones|*TU
- MeSH Heading
- Animal; English Abstract; Female; Mice
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0031-2991
- Country of Publication
- USSR
Record 4 from database: MEDLINE
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- Title
- Ineffectiveness of dimethyl sulfone as a cryoprotectire
agent.
- Author
- Connor KW; Ashwood Smith MJ
- Address
-
- Source
- Cryobiology, 1973 Apr, 10:1, 87-8
- Abstract
- Abstract unavailable online.
- Language of Publication
- English
- Unique Identifier
- 73185091
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- MeSH Heading (Major)
- Blood Preservation|*; Sulfones|*
- MeSH Heading
- Animal; Cattle; Cryoprotective Agents; Dimethyl Sulfoxide;
Erythrocytes; Freezing; Hemolysis; Human
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0011-2240
- Country of Publication
- UNITED STATES
Record 5 from database: MEDLINE
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- Title
- Deformylation of 4,4'-diformamidodiphenyl sulfone (DFD) by
plasma of certain mammals.
- Author
- Gleason LN; Vogh BP
- Address
-
- Source
- Biochem Pharmacol, 1971 Sep, 20:9, 2409-16
- Abstract
- Abstract unavailable online.
- Language of Publication
- English
- Unique Identifier
- 74014895
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- MeSH Heading (Major)
- Antimalarials|*BL; Formates|*ME; Sulfones|*BL
- MeSH Heading
- Amines|ME; Aminobenzoic Acids|ME; Animal; Chromatography,
Thin Layer; Dealkylation; Diazonium Compounds|ME; Dimethyl
Sulfoxide; Erythrocytes|ME; Guinea Pigs; In Vitro; Kinetics;
Mice; Rabbits; Rats; Species Specificity; Sulfadiazine|ME;
Sulfanilamides|ME
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0006-2952
- Country of Publication
- UNITED STATES
Record 6 from database: MEDLINE
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- Title
- Desulfurization of dibenzothiophene by Corynebacterium sp.
strain SY1.
- Author
- Omori T; Monna L; Saiki Y; Kodama T
- Address
- Department of Agricultural Chemistry, Faculty of
Agriculture, University of Tokyo, Japan.
- Source
- Appl Environ Microbiol, 1992 Mar, 58:3, 911-5
- Abstract
- Strain SY1, identified as a Corynebacterium sp., was
isolated on the basis of the ability to utilize
dibenzothiophene (DBT) as a sole source of sulfur. Strain
SY1 could utilize a wide range of organic and inorganic
sulfur compounds, such as DBT sulfone, dimethyl sulfide,
dimethyl sulfoxide, dimethyl sulfone, CS2, FeS2, and even
elemental sulfur. Strain SY1 metabolized DBT to
dibenzothiophene-5-oxide, DBT sulfone, and
2-hydroxybiphenyl, which was subsequently nitrated to
produce at least two different hydroxynitrobiphenyls during
cultivation. These metabolites were separated by silica gel
column chromatography and identified by nuclear magnetic
resonance, UV, and mass spectral techniques. Resting cells
of SY1 desulfurized toluenesulfonic acid and released
sulfite anion. On the basis of these results, a new DBT
degradation pathway is proposed.
- Language of Publication
- English
- Unique Identifier
- 92246502
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- MeSH Heading (Major)
- Corynebacterium|GD/*ME; Sulfur|*ME; Thiophenes|*ME
- MeSH Heading
- Biodegradation; Chromatography; Kinetics; Sulfites|ME
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0099-2240
- Country of Publication
- UNITED STATES
Record 7 from database: MEDLINE
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- Title
- Effects of dimethyl sulfone (DMSO2) on early gametogenesis
in Caenorhabditis elegans: ultrastructural aberrations and
loss of synaptonemal complexes from pachytene nuclei.
- Author
- Goldstein P; Magnano L; Rojo J
- Address
- Department of Biological Sciences, University of Texas, El
Paso 79968.
- Source
- Reprod Toxicol, 1992, 6:2, 149-59
- Abstract
- The free-living nematode Caenorhabditis elegans has been
used extensively for studies in developmental and
reproductive genetics. Recently, toxicologic studies have
been initiated using specific sex chromosome mutations. In
the present study, high incidence of male (him) mutants,
him-5 and him-8, were treated with dimethyl sulfone (DMSO2),
the primary metabolite of dimethyl sulfoxide (DMSO). In
addition to differential effects on X-chromosome
nondisjunction, loss of viability and fertility were
observed. Much lower concentrations of DMSO2 were required
to elicit the same aberrational effects characteristic of
DMSO (1); thus, the toxicity of the former was significantly
more potent. The observed decrease in life span was
associated with senescent morphology of meiotic prophase
nuclei, such that nuclei from young and old specimens could
not be differentiated. Aging in oocytes at pachytene is
characterized by nucleo-cytoplasmic aberrations, increased
density of the nucleoplasm and cytoplasm, and decrease in
numbers of mitochondria. Increasing concentrations of DMSO2
resulted in a corresponding decrease in fertility and
increased production of abnormal gametes. At DMSO2
concentrations higher than 1.0%, synaptonemal complexes (SC)
were absent from pachytene nuclei; thus, effective pairing
and segregation of homologous chromosomes was prohibited.
Since the SC is essential for regulating pairing and
subsequent separation of bivalents, the lack of an SC
explains the loss of fertility, due to the production of
unbalanced gametes, observed in DMSO2-treated specimens.
- Language of Publication
- English
- Unique Identifier
- 92273960
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- MeSH Heading (Major)
- Caenorhabditis|*DE/UL; Gametogenesis|*DE; Meiosis|*DE;
Mutagens|*; Sulfones|PK/*TO
- MeSH Heading
- Animal; Female; Male; Microscopy, Electron;
Mitochondria|UL; Support, U.S. Gov't, P.H.S.
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0890-6238
- Country of Publication
- UNITED STATES
Record 8 from database: MEDLINE
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- Title
- Syntheses and biologic studies of steroidal methyl
sulfides and sulfones.
- Author
- Shafiullah; Dua PR; Srimal RC; Ansari SA
- Address
- Department of Chemistry, Aligarh Muslim University, India.
- Source
- Steroids, 1991 Nov, 56:11, 562-5
- Abstract
- Reactions of cholest-5-ene (I) and its 3 beta-chloro (II)
and 3 beta-acetoxy (III) analogs with
trimethylchlorosilane-dimethyl sulfoxide in dry acetonitrile
furnish cholest-4-en-6 beta-yl methyl sulfide (IV) and its 3
beta-chloro (V) and 3 beta-acetoxy (VI) analogs. Oxidation
of (IV) with m-chloroperbenzoic acid affords cholest-4-en-6
beta-yl methyl sulfone (VII) and 4 alpha, 5-epoxy-5
alpha-cholestan-6 beta-yl methyl sulfone (VIII). Under
similar reaction conditions, V furnishes 3
beta-chlorocholest-4-en-6 beta-yl methyl sulfone (IX), while
VI gives 3 beta-acetoxycholest-4-en-6 beta-yl methyl sulfone
(X) and 3 beta-acetoxy-4 alpha, 5-epoxy-5 alpha-cholestan-6
beta-yl methyl sulfone (XI). The structures of these
compounds were established on the basis of analytic and
spectral data. Some of these compounds have been evaluated
for their possible biologic activities.
- Language of Publication
- English
- Unique Identifier
- 92263386
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- MeSH Heading (Major)
- Autonomic Nervous System|*DE; Blood Pressure|*DE; Central
Nervous System|*DE; Steroids|*CS/PD; Sulfides|*CS/PD;
Sulfones|*CS/PD
- MeSH Heading
- Animal; Cats; Mice; Molecular Structure; Support, Non-U.S.
Gov't
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0039-128X
- Country of Publication
- UNITED STATES
Record 9 from database: MEDLINE
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- Title
- Effect of dimethyl sulfoxide on sulindac disposition in
rats.
- Author
- Swanson BN; Mojaverian P; Boppana VK; Dudash MR
- Address
-
- Source
- Drug Metab Dispos, 1981 Nov, 9:6, 499-502
- Abstract
- Sulindac and dimethyl sulfoxide (DMSO) are both effective
antiinflammatory agents in man. Since the sulfoxide moiety
in these compounds is metabolized similarly, a biochemical
interaction between the two drugs in vivo was thought to be
possible. After iv injections of sulindac (5 mg/kg), plasma
concentrations of sulindac, and its sulfide and sulfone
metabolites, were measured in normal rats and in rats that
had received, 30 min earlier, a single ip dose of DMSO (0.1,
0.5, or 1.0 ml). The half-life of sulindac (normally 94 min)
was increased significantly by DMSO (0.1, 0.5, or 1.0 ml).
The half-life of sulindac (normally 94 min) was increased
significantly by DMSO (408 min after 1.0 ml of DMSO). Plasma
sulfide metabolite levels were reduced in a dose-related
manner by DMSO (93% reduction in peak concentration after
1.0 ml of DMSO). Sulfone metabolite concentration was also
significantly diminished by the highest dose of DMSO.
Similarly, DMSO was shown to decrease conversion of sulindac
to sulfide and sulfone metabolites by rat liver enzymes in
vitro. Sulfoxide reductase was more sensitive to DMSO
inhibition than was sulfoxide oxidase both in vivo and in
vitro. These data demonstrate that DMSO can significantly
alter in vivo the formation of the pharmacologically active,
sulfide metabolite of sulindac; therefore, concurrent use of
DMSO and sulindac should be approached with caution.
- Language of Publication
- English
- Unique Identifier
- 82138346
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- MeSH Heading (Major)
- Dimethyl Sulfoxide|ME/*PD; Indenes|*ME; Liver|*ME;
Sulindac|AA/*ME
- MeSH Heading
- Animal; Dose-Response Relationship, Drug; Drug
Interactions; Half-Life; Kinetics; Male; Rats; Rats, Inbred
Strains; Support, Non-U.S. Gov't
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0090-9556
- Country of Publication
- UNITED STATES
Record 10 from database: MEDLINE
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- Title
- Dimethyl sulfone: isolation from human urine.
- Author
- Williams KI; Burstein SH; Layne DS
- Address
-
- Source
- Arch Biochem Biophys, 1966 Jan, 113:1, 251-2
- Abstract
- Abstract unavailable online.
- Language of Publication
- English
- Unique Identifier
- 66160160
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- MeSH Heading (Major)
- Sulfones|*
- MeSH Heading
- Adult; Child; Child, Preschool; Chromatography, Gas;
Female; Human; In Vitro; Male; Urine
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0003-9861
- Country of Publication
- UNITED STATES
Record 11 from database: MEDLINE
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- Title
- Dimethyl sulfone: isolation from cows' milk.
- Author
- Williams KI; Burstein SH; Layne DS
- Address
-
- Source
- Proc Soc Exp Biol Med, 1966 Jul, 122:3, 865-6
- Abstract
- Abstract unavailable online.
- Language of Publication
- English
- Unique Identifier
- 67017073
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- MeSH Heading (Major)
- Milk|*AN; Sulfones|*AN
- MeSH Heading
- Animal; Cattle; Chemistry; Chromatography, Gas; In Vitro
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0037-9727
- Country of Publication
- UNITED STATES
Record 12 from database: MEDLINE
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- Title
- Sulfone metabolite of sulindac inhibits mammary
carcinogenesis.
- Author
- Thompson HJ; Jiang C; Lu J; Mehta RG; Piazza GA; Paranka
NS; Pamukcu R; Ahnen DJ
- Address
- AMC Cancer Research Center, Lakewood, Colorado 80214, USA.
- Source
- Cancer Res, 1997 Jan, 57:2, 267-71
- Abstract
- Sulindac sulfoxide, a commonly prescribed
anti-inflammatory drug, has cancer chemopreventive activity.
During its metabolism, the inactive prodrug sulindac
sulfoxide undergoes either reduction to the active
anti-inflammatory metabolite sulindac sulfide or
irreversible oxidation to sulindac sulfone, which lacks
prostaglandin synthetase inhibitory activity. Interestingly,
sulindac sulfone has been reported to have cancer
chemopreventive activity. The objective of the experiments
reported here was to investigate the chemopreventive
activity of sulindac sulfone against mammary carcinogenesis
and to study its mechanism. Rats were injected with either
12.5 or 37.5 mg of 1-methyl-1-nitrosourea (MNU)/kg body
weight at 50 days of age. Sulindac sulfone was incorporated
into a purified diet at a concentration of either 0.03 or
0.06% (w/w) and fed to rats beginning 7 days after the
injection of MNU. Sulindac sulfoxide at a level of 0.06%
(w/w) was fed as a reference for comparison. Thirty rats
were assigned to each dietary group treated with the high
dose of MNU, and 44 rats were assigned to each dietary group
treated with the low dose of MNU. The sulfone reduced cancer
incidence and the number of cancers per rat irrespective of
the dose of MNU injected, and its chemopreventive activity
was comparable to that of sulindac sulfoxide. Cancer latency
was also prolonged significantly by sulindac sulfone; the
effect was particularly notable at the low dose of
carcinogen, at which the prolongation of latency was >8
weeks. The sulfone inhibited the occurrence of mammary
carcinomas that were classified as having either a wild-type
or a mutant codon 12 in the Ha-ras gene; however, the
inhibitory effect was greater against carcinomas with a
mutant Ha-ras genotype. Using a mammary gland organ culture
transformation assay, it was observed that sulindac sulfone
also inhibited the formation of
7,12-dimethylbenz(a)anthracene-induced hyperplastic alveolar
nodules and that the inhibitory activity of the sulfone was
comparable to that of the sulfoxide. These data indicate
that the observed effect of the sulfone on mammary
carcinogenesis in vivo is likely to be due to a
tissue-specific effect rather than to other systemic
effects. The findings that both the prodrug and the sulfone
inhibited carcinogenesis in vivo and nodule formation in
organ culture and that the sulfone lacks inhibitory activity
on prostaglandin synthesis suggest a mechanism(s) of
chemoprevention that is independent of the prostaglandin
pathway. A candidate mechanism for the apparent clonal
selection pressure exerted by the sulfone against mammary
carcinogenesis is apoptosis. To test this hypothesis, MCF-7
cells were exposed to a range of concentrations of sulindac
sulfone and sulfoxide. Both compounds inhibited cell growth
and induced apoptosis in the absence of necrosis.
Collectively, these data support a specific chemopreventive
effect of sulindac sulfone against mammary carcinogenesis
and indicate that this compound may have a selective effect
against carcinogenesis involving alterations in the signal
transduction cascade of which Ha-ras is a component.
Evidence is consistent with the involvement of apoptosis in
the cancer-inhibitory activity observed.
- Language of Publication
- English
- Unique Identifier
- 97153276
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- MeSH Heading (Major)
- Antineoplastic Agents|*TU; Mammary Neoplasms,
Experimental|CI/GE/*PC; Sulindac|*AA/TU
- MeSH Heading
- Animal; Carcinogens|AD; Drug Screening Assays, Antitumor;
Female; Genes, ras; Methylnitrosourea|AD; Organ Culture;
Rats; Rats, Sprague-Dawley; Support, Non-U.S. Gov't;
Support, U.S. Gov't, Non-P.H.S.;
9,10-Dimethyl-1,2-benzanthracene
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0008-5472
- Country of Publication
- UNITED STATES
Record 13 from database: MEDLINE
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- Title
- Persistence of fensulfothion in a sandy-loam soil and
uptake by rutabagas, carrots and radishes using microplots.
- Author
- Greenhalgh R; Read DC
- Address
-
- Source
- J Environ Sci Health [B], 1981, 16:3, 363-79
- Abstract
- Field microplots were treated with 141 and 282 ppm
fensulfothion and 37.1 and 74.2 ppm fensulfothion sulfone.
These concentrations are equivalent to field treatment rates
of 8.48 and 16.96 kg AI/ha, fensulfothion, and 2.23 and 4.47
kg AI/ha, fensulfothion sulfone, respectively, for banded
application (10 cm wide, rows 80 cm apart). The half-lives
in a sandy loam soil were 30-39 and 14-23 days,
respectively. Fensulfothion sulfone and sulfide were the
main derivatives found in fensulfothion treated soil. The
maximum levels of these derivatives were 21.22 and 22.95 ppm,
respectively for the 8.48 kg/ha treatment and 33.90 and
42.45 ppm, respectively, for the higher treatment, which
occurred between 30-60 days. Carrots appeared to take up
more fensulfothion from soil than rutabagas or radishes. The
residue levels at harvest decreased in the order carrot peel
greater than pulp greater than rutabagas root greater than
peel greater than pulp. Residue levels of fensulfothion and
sulfone in radishes were similar to those found in
rutabagas. The ratio sulfoxide/sulfone in rutabagas ranged
from 0.4-1.5 and in carrots from 1.7-7.6. This phenomenon is
thought to be due to oxidative enzyme systems present in
rutabagas. Dimethyl phosphorothioic acid, but not dimethyl
phosphoric acid was detected (max. 1.33 ppm) in some
rutabagas samples but not in carrots.
- Language of Publication
- English
- Unique Identifier
- 81240591
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- MeSH Heading (Major)
- Insecticides, Organothiophosphate|*AN;
Organothiophosphorus Compounds|AA/*AN/ME; Soil
Pollutants|*AN; Vegetables|*AN
- MeSH Heading
- Brassica|ME; Dose-Response Relationship, Drug; Drug
Stability; Half-Life; Pesticide Residues|AN; Plants,
Edible|ME
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0360-1234
- Country of Publication
- UNITED STATES
Record 14 from database: MEDLINE
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- Title
- Structure-activity relationships of retinoids in
developmental toxicology. IV. Planar Cisoid conformational
restriction.
- Author
- Willhite CC; Dawson MI
- Address
- Department of Health Services, State of California, Toxic
Substances Control Program, Berkeley 94710.
- Source
- Toxicol Appl Pharmacol, 1990 Apr, 103:2, 324-44
- Abstract
- To evaluate the influence of the three-dimensional
configuration of retinoids on teratogenic activity, 14
retinoids were studied in hamsters. Retinoids with a
conformational restriction of the retinoic acid polyene
chain adjacent to the beta-cyclogeranylidene ring showed
increased teratogenic potency and retinoids with aromatic
conformational restriction adjacent to the polar terminus
showed potency equivalent to retinoic acid. Conformational
restriction of the polyene chain that permits rotation of
the bond adjacent to the beta-cyclogeranylidene ring
abolished teratogenic activity. Incorporation of dimethyl
substituents at positions corresponding to C1 and C4
positions of retinoic acid enhanced teratogenic potency.
Elimination of the twist chair conformation of gem-dimethyl
substituents via incorporation of a benzothiopyran or
substituted planar aromatic ring decreased teratogenic
potency. Planar cisoid conformational restriction alone was
insufficient to confer teratogenic activity in that
elimination of the polar terminus abolished teratogenic
activity. That an acidic polar terminus, as contrasted to a
carboxyl residue per se, was required for teratogenic
activity was illustrated by administration of a retinoidal
phenyl sulfone which was metabolized to the corresponding
teratogenic sulfonic acid. Retinoid teratogenicity in
hamsters depends upon the assumption of a 10,11 cisoid
and/or 12,13 cisoid rotameric form by a conjugated spacer
greater than five carbon atoms in length located between a
hydrophobic ring system and an acidic terminus, ionized at
physiologic pH. Comparison of the relative teratogenic
potencies of this series of conformationally restricted
retinoids with their activities in assays for
chemoprevention activity showed that those analogs with high
intrinsic control of epithelial or mesenchymal cell
differentiation were also the more potent teratogens. The
results suggest that those biochemical mechanisms
responsible for retinoid control of normal adult or
neoplastic cell differentiation also mediate retinoid-induced
teratogenesis.
- Language of Publication
- English
- Unique Identifier
- 90232521
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- MeSH Heading (Major)
- Abnormalities, Drug-Induced|*; Fetal Development|*DE;
Fetal Diseases|*CI; Retinoids|*TO
- MeSH Heading
- Animal; Comparative Study; Dose-Response Relationship,
Drug; Female; Fetal Death; Fetal Resorption; Hamsters;
Molecular Conformation; Pregnancy; Structure-Activity
Relationship; Support, U.S. Gov't, P.H.S.
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0041-008X
- Country of Publication
- UNITED STATES
Record 15 from database: MEDLINE
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- Title
- Unexpected similarity of the structures of the weakly
toxic amanitin (S)-sulfoxide and the highly toxic (R)-sulfoxide
and sulfone as revealed by proton nuclear magnetic resonance
and X-ray analysis.
- Author
- Wieland T; Götzendörfer C; Dabrowski J; Lipscomb WN;
Shoham G
- Address
-
- Source
- Biochemistry, 1983 Mar, 22:5, 1264-71
- Abstract
- The three-dimensional structures of the slightly toxic
diastereomeric (S)-sulfoxide of 6'-O-methyl-alpha-amanitin
[6'-O-Me-alpha-ama (S)-sulfoxide, 4] and of the
corresponding highly toxic sulfone 5 have been determined by
X-ray diffraction analysis. The same derivatives along with
6'-O-methyl-alpha-amanitin [O-Me-alpha-ama (R)-sulfoxide, 3]
and the corresponding thioether (O-Me-alpha-ama sulfide, 6]
have been investigated in dimethyl sulfoxide solutions by
360-MHz 1H NMR spectroscopy including nuclear Overhauser
effects (NOE). In addition alpha-amanitin (2) has been
reinvestigated by this high-resolution method involving the
identification of the ABMX systems of the tryptophan,
cysteine, and asparagine and discrimination between the
glycine residues. The structures of compounds 2-6 are
compared with the structure of beta-amanitin which was
solved previously by X-ray structure analysis. The results
are (1) the structures in the crystalline state of the (S)-sulfoxide
4 and sulfone 5 are practically identical and (2) in
dimethyl sulfoxide solution the structures of compounds 4
and 5 are likewise identical with each other and with those
of the (R)-sulfoxide 3 and the thioether 6. The general
structure of the peptide backbone of the alpha-amanitin
derivatives investigated here almost corresponds to that of
beta-amanitin (1), the main difference being a rotated plane
of the peptide bond between the asparagine and cysteine
residue. In order to explain the lack of high toxicity in
the (S)-sulfoxide 4 we tentatively suggest alternative
hydrogen bonding of a donor from the protein, or
displacement of the R oxygen to the S oxygen of a hydrogen
bond donor. This alternative bonding or displacement might
not occur in the sulfoxide 4. Other explanations which
include local conformational changes in the inhibitors or a
difference between the SO and SO2 local dipoles are also
possible.
- Language of Publication
- English
- Unique Identifier
- 83178939
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- MeSH Heading (Major)
- Amanitins|*/TO
- MeSH Heading
- Mathematics; Nuclear Magnetic Resonance; Stereoisomerism;
Support, U.S. Gov't, P.H.S.; X-Ray Diffraction
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0006-2960
- Country of Publication
- UNITED STATES
Record 16 from database: MEDLINE
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- Title
- Cloning and characterization of genes encoding an enzyme
which oxidizes dimethyl sulfide in Acinetobacter sp. strain
20B.
- Author
- Horinouchi M; Kasuga K; Nojiri H; Yamane H; Omori T
- Address
- Biotechnology Research Center, University of Tokyo, Japan.
- Source
- FEMS Microbiol Lett, 1997 Oct, 155:1, 99-105
- Abstract
- Acinetobacter sp. strain 20B was isolated based on the
ability to utilize dimethyl sulfide as the sole sulfur
source. Since strain 20B oxidized indole as well as dimethyl
sulfide, indigo production by recombinant Escherichia coli
clones carrying Acinetobacter DNA was used as a selection
for cloning genes encoding dimethyl sulfide oxidation genes.
The gene encoding an indole-oxidizing enzyme was also found
to oxidize dimethyl sulfide. The dimethyl sulfide-oxidizing
enzyme genes consisted of six open reading flames designated
dsoABCDEF. The deduced amino acid sequences of dsoABCDEF
were homologous with those of the multicomponent phenol
hydroxylases. DsoABCDEF oxidized dimethyl sulfide to
dimethyl sulfoxide, and dimethyl sulfoxide to dimethyl
sulfone.
- Language of Publication
- English
- Unique Identifier
- 98005684
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- MeSH Heading (Major)
- Acinetobacter|*EN/*GE/ME; Genes, Bacterial|*; Sulfides|*ME
- MeSH Heading
- Cloning, Molecular; Comparative Study; Escherichia coli|GE;
Hydroxylases|GE/ME; Oxidation-Reduction; Oxygenases|GE/ME;
Restriction Mapping; Substrate Specificity
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0378-1097
- Country of Publication
- NETHERLANDS
Record 17 from database: MEDLINE
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- Title
- Biological effects of the metabolites of dimethyl
sulfoxide.
- Author
- Kocsis JJ; Harkaway S; Snyder R
- Address
-
- Source
- Ann N Y Acad Sci, 1975 Jan, 243:, 104-9
- Abstract
- In summary, the effects of dimethyl sulfoxide (DMSO) and
its metabolites, dimethyl sulfone (DMSO2) and dimethyl
sulfide (DMS), were studied in five selected systems in rats
and mice. DMSO enhanced the taurine excretion and the
lethality produced by such aromatic hydrocarbons as benzene
and chlorobenzene in rats. In mice, DMSO decreased the
toxicity such cholinesterase inhibitors as paraoxon and
octamethyl pyrophosphoramide. DMSO also lowered the body
temperture of rats and reduced the motor activity of mice.
Although DMSO2, the major metabolite of DMSO, was not
effective in increasing the lethality of solvent
hydrocarbons, it seemed to be quite as effective with
respect to the other effects. DMS, although quite potent
with respect to lowering body temperature and reducing motor
activity, was relatively ineffective otherwise. Thus each of
the metabolites has a spectrum of activity different from
the parent compound; DMSO has the widest spectrum and DMS
the narrowest. It remains to be determined whether the
therapeutic effects of DMSO are related to the experimental
effects reported above in animals, and whether DMSO2 and DMS
may share any of the therapeutic effects of DMSO.
- Language of Publication
- English
- Unique Identifier
- 75163079
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- MeSH Heading (Major)
- Dimethyl Sulfoxide|*AA/ME/PD; Sulfur Oxides|*PD
- MeSH Heading
- Animal; Benzene|TO; Body Temperature|DE; Cholinesterase
Inhibitors|TO; Depression, Chemical; Drug Synergism;
Hydrocarbons|TO; Hypnotics and Sedatives|PD; Lethal Dose 50;
Mice; Motor Activity|DE; Rats; Support, U.S. Gov't, Non-P.H.S.;
Taurine|ME/UR; Time Factors; Tranquilizing Agents|PD
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0077-8923
- Country of Publication
- UNITED STATES
Record 18 from database: MEDLINE
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- Title
- A possible chemical explanation for the events associated
with the death of Gloria Ramirez at Riverside General
Hospital [see comments]
- Author
- Grant PM; Haas JS; Whipple RE; Andresen BD
- Address
- Forensic Science Centre, Lawrence Livermore National
Laboratory, Livermore, CA 94550, USA.
- Source
- Forensic Sci Int, 1997 Jun, 87:3, 219-37
- Abstract
- The events associated with the death of Gloria Ramirez at
Riverside General Hospital on 19 February 1994 have been
portrayed as a major medical mystery. A potential chemical
explanation for this incident has been developed. The
hypothetical scenario depends upon the oxidation of a common
solvent, dimethyl sulfoxide, through dimethyl sulfone to
dimethyl sulfate. The latter compound is a volatile and
highly toxic agent that can be quite hazardous to humans in
small amounts. It is also environmentally nonpersistent.
Much of the mystery surrounding the circumstances at the
hospital may be explainable if this postulated metabolic
pathway took place at the time of the emergency room
incident. Although dimethyl sulfate was not detected in any
analyses pertinent to this event, there are plausible
scientific explanations to account for that fact. The
sulfate anion, a hydrolysis product of dimethyl sulfate, was
measured at an appreciably elevated concentration in
Ramirez' blood. The descriptions of the symptoms of the
hospital-staff victims appear quite consistent with dimethyl
sulfate exposures. This paper attempts to make some sense of
the reported data and eyewitness accounts, and perhaps
provide new insight for any future research that could
further explain this reported occurrence of toxic exposure.
- Language of Publication
- English
- Unique Identifier
- 97391234
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- MeSH Heading (Major)
- Cause of Death|*; Dimethyl Sulfoxide|*ME; Forensic
Medicine|*MT; Mutagens|ME/*PO; Sulfones|*ME; Sulfuric Acid
Esters|ME/*PO
- MeSH Heading
- Blood Chemical Analysis; California; Emergency Service,
Hospital; Human; Oxidation-Reduction
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0379-0738
- Country of Publication
- IRELAND
Record 19 from database: MEDLINE
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- Title
- Identification of biotin sulfone, bisnorbiotin methyl
ketone, and tetranorbiotin-l-sulfoxide in human urine.
- Author
- Zempleni J; McCormick DB; Mock DM
- Address
- Department of Pediatrics, University of Arkansas for
Medical Sciences, Little Rock, USA.
- Source
- Am J Clin Nutr, 1997 Feb, 65:2, 508-11
- Abstract
- In previous studies using the HPLC and avidin-binding
assay, five unidentified avidin-binding substances were
observed in human urine. The present study investigated the
identity of these substances. Urine was collected before and
after intravenous administration of 18.5 mumol biotin to
healthy adults. Unknown substances 1 and 3 were initially
identified as biotin sulfone and bisnorbiotin methyl ketone,
respectively, by coelution with authentic standards on HPLC.
Identities were confirmed by thin-layer chromatography and
by derivatization with p-dimethyl-aminocinnamaldehyde. As
expected for biotin metabolites, the urinary excretion of
biotin sulfone and bisnorbiotin methyl ketone increased with
biotin administration. The urinary excretion of biotin
sulfone increased 21-fold from 0.2 nmol/h before to 4.2 nmol/h
after administration; the excretion of bisnorbiotin methyl
ketone increased 130-fold from 0.4 to 51.8 nmol/h. At
presumed steady state in free-living subjects (n = 6),
biotin sulfone and bisnorbiotin methyl ketone accounted for
3.6% and 7.9% of total biotin excretion, respectively.
Traces of tetranorbiotin-l-sulfoxide were also identified by
using thin-layer chromatography and derivatization with p-dimethylaminocinnamaldehyde.
However, tetranorbiotin-l-sulfoxide was not detectable in
urine by the HPLC and avidin-binding assay because this
metabolite has weak avidin-binding affinity. We conclude
that biotin sulfone and bisnorbiotin methyl ketone are
present in measurable quantities in human urine; their
quantitation should allow more accurate studies on human
biotin metabolism and turnover.
- Language of Publication
- English
- Unique Identifier
- 97174877
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- MeSH Heading (Major)
- Biotin|*AA/AD/*ME/UR; Sulfones|*UR; Sulfoxides|*UR
- MeSH Heading
- Adult; Chromatography, High Pressure Liquid|MT;
Chromatography, Thin Layer|MT; Female; Human; Injections,
Intravenous; Male; Support, U.S. Gov't, P.H.S.
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0002-9165
- Country of Publication
- UNITED STATES
Record 20 from database: MEDLINE
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- Title
- Permeation of lipophilic drugs through synthetic
elastomers.
- Author
- Bruck SD; Kojima M; Kadoma Y; Masuhara E
- Address
-
- Source
- Med Prog Technol, 1983, 10:3, 161-9
- Abstract
- Permeability studies were carried out with three
lipophilic drugs, namely, phenytoin and primidone (both
widely used in the treatment of epilepsies and convulsive
disorders), and dapsone (a sulfone antimicrobial agent used
in the treatment of leprosy and to a lesser extent in
dermatitis herpetiformis) through silica-filled
poly(dimethyl siloxane) (Silastic) membranes, and
anisotropic membranes of poly(ether-urethane)/poly(dimethyl
siloxane) block copolymer (Avcothane, Cardiothane). These
polymers are used in medical implants and in various
cardiovascular devices. While both polymers were permeable
to the drugs, the transport properties differed
significantly. In the case of the poly(dimethyl siloxane)
there was an initial large burst effect, followed by an
exponential decrease in the rate of drugs released through
the polymer films, although with dapsone the release rate
became essentially constant between 100-180 h at 37 degrees
C. In the case of the anisotropic films of the poly(ether-urethane)/poly(dimethyl
siloxane) block copolymer, the permeabilities were much
higher. Significantly, phenytoin exhibited essentially
constant rate (zero-order) kinetics between 25-150 h,
showing only a moderate burst effect that is probably not
significant therapeutically. Importantly, dapsone showed
neither a burst effect nor any significant time lag, and the
release followed constant rate (zero-order) kinetics between
12-80 h, followed by only a moderate decrease in drug
concentration up to 140 h (the experimental end-point). The
diffusion coefficients calculated from initial desorption
data at 37 degrees C for the poly(ether-urethane)/poly(dimethyl
siloxane) block copolymer are as follows: phenytoin = 8.6 X
10(-9) cm2/s, primidone = 2.8 X 10(-9) cm2/s, and dapsone =
2.4 X 10(-8) cm2/s.(ABSTRACT TRUNCATED AT 250 WORDS)
- Language of Publication
- English
- Unique Identifier
- 85110700
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- MeSH Heading (Major)
- Dapsone|*ME; Membranes, Artificial|*; Phenytoin|*ME;
Polymers|*; Primidone|*ME; Silicone Elastomers|*
- MeSH Heading
- Kinetics; Microscopy, Electron, Scanning; Permeability;
Polyurethanes; Support, Non-U.S. Gov't; Time Factors
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0047-6552
- Country of Publication
- GERMANY, WEST
Record 21 from database: MEDLINE
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- Title
- DMSO is a substrate for chloroperoxidase.
- Author
- Geigert J; DeWitt SK; Neidleman SL; Lee G; Dalietos DJ;
Moreland M
- Address
-
- Source
- Biochem Biophys Res Commun, 1983 Oct, 116:1, 82-5
- Abstract
- Dimethyl sulfoxide has been used as a nonaqueous organic
solvent in haloperoxidase reactions. However, it has been
found that this solvent is not inert under chloroperoxidase
reaction conditions, forming the halosulfoxide, the sulfone,
and the halosulfone. The biological significance of this
finding is briefly discussed.
- Language of Publication
- English
- Unique Identifier
- 84052565
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- MeSH Heading (Major)
- Chloride Peroxidase|*ME; Dimethyl Sulfoxide|*ME;
Peroxidases|*ME
- MeSH Heading
- Fungi|EN; Oxidation-Reduction
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0006-291X
- Country of Publication
- UNITED STATES
Record 22 from database: MEDLINE
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- Title
- Induction of NAD(P)H:quinone reductase in human peripheral
blood lymphocytes.
- Author
- Gordon GB; Prochaska HJ; Yang LY
- Address
- Department of Pharmacology and Molecular Sciences, Johns
Hopkins University School of Medicine, Baltimore, MD 21205.
- Source
- Carcinogenesis, 1991 Dec, 12:12, 2393-6
- Abstract
- The induction of quinone reductase [QR; NAD(P)H:(quinone
acceptor) oxidoreductase; EC 1.6.99.2] in cultured cells and
animal tissues of rodents has provided useful information on
mechanisms of protection against carcinogens. We have
developed a simple and efficient microtiter plate assay for
the direct measurement of QR basal activity and inducibility
in human peripheral blood lymphocytes (unstimulated, mitogen-stimulated
and Epstein-Barr virus-transformed) grown in suspension
culture. In these cells, QR was induced by monofunctional (electrophilic)
inducers (i.e. 1,2-dithiole-3-thione, dimethyl fumarate,
methyl vinyl sulfone) but not by bifunctional inducers (i.e.
1,1'-azonaphthalene, beta-naphthoflavone,
2,3,7,8-tetrachlorodibenzo-p-dioxin). QR is a major enzyme
of xenobiotic metabolism that carries out obligatory
two-electron reductions and thereby protects cells against
the toxicity of quinones. It is induced in many tissues
coordinately with other enzymes that protect against
electrophiles. Since lymphocytes can be sampled easily and
repetitively in man, this system may provide a simple
short-term marker for assessing the capacity of tissues to
detoxify electrophiles, such as quinones, and for measuring
the response to inducers.
- Language of Publication
- English
- Unique Identifier
- 92083635
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- MeSH Heading (Major)
- Lymphocytes|DE/*EN; NAD(P)H Dehydrogenase (Quinone)|*BI/BL
- MeSH Heading
- Adult; Aged; Cell Transformation, Viral|PH; Cells,
Cultured; Enzyme Induction; Female; Fumarates|PD;
Herpesvirus 4, Human|PH; Human; Lymphocyte Transformation|PH;
Male; Middle Age; Mitogens|PD; Sulfones|PD; Support, Non-U.S.
Gov't; Support, U.S. Gov't, P.H.S.; Thiones|PD;
Thiophenes|PD
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0143-3334
- Country of Publication
- UNITED STATES
Record 23 from database: MEDLINE
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- Title
- Effect of cross-linking agents on insulin associated
responses in adipocytes.
- Author
- Goren HJ; Kahn CR
- Address
-
- Source
- Can J Biochem, 1982, 60:10, 987-1000
- Abstract
- The effect of 10 bifunctional cross-linking agents and
four monofunctional analogues was studied on isolated
adipocytes. [125I]Insulin binding and degradation, basal and
insulin-stimulated glucose oxidation, and 3-O-methyl glucose
uptake were measured. Two cross-linkers, which possess
succinimide ester residues (disuccinimidyl suberate and
dithiobis(succinimidyl propionate)) and react selectively
with amino groups, appeared to react relatively specifically
with the insulin receptor. Both produced a slight
stimulation of basal glucose transport and metabolism, a
marked inhibition of insulin-stimulated glucose transport
and metabolism, and a marked decrease in insulin binding.
Pretreatment of cells with unlabelled insulin partially
blocked the effect of disuccinimidyl suberate, and as has
been previously shown, disuccinimidyl suberate cross-linked
insulin to its receptor. A monofunctional analogue of these
compounds was 100-fold less active in altering cellular
metabolic activity. Bisimidates, such as dimethyl
suberimidate, dimethyl adipimidate, and dimethyl
dithiobispropionimidate, also react with free amino groups
but are more hydrophilic. These agents produced similar
effects on glucose oxidation as the succinimide esters, but
had little or no effect on insulin binding. The effects of
these agents are not blocked by insulin and they do not
cross-link insulin to its receptor. Mixed bifunctional
reagents containing either a succinimide ester or an imidate
and a group which reacts with thiols produced effects
similar to the cross-linkers containing two succinimide
groups or bisimidates, respectively. The bifunctional
arylating agents difluorodinitrobenzene and
bis(fluoronitrophenyl)sulfone produce marked effects on
insulin binding and glucose oxidation at micromolar
concentrations, but the monofunctional analogue
fluorodinitrobenzene is almost equally active suggesting
that with these compounds chemical modifications and not
cross-linking was important. With neither the mixed
bifunctional reagents, nor the arylating agents, did insulin
pretreatment alter the effect of cross-linker and none of
these agents cross-linked [125I]insulin to its receptor.
These data suggest that the insulin receptor possesses a
free amino group in a hydrophobic environment in its active
site. A reactive amino group in a hydrophilic environment as
well as other reactive groups are also present in some
component of the insulin receptor-effector complex. Chemical
modification or cross-linking of these functional groups
results in an inhibition or mimicking of insulin action.
Further study will be required to identify the exact locus
of these sites.
- Language of Publication
- English
- Unique Identifier
- 83076688
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- MeSH Heading (Major)
- Adipose Tissue|*ME; Cross-Linking Reagents|*PD;
Insulin|*ME; Receptors, Insulin|*ME
- MeSH Heading
- Animal; Cells, Cultured; Glucose|ME; Male; Rats; Rats,
Inbred Strains; Succinimides|PD; Support, Non-U.S. Gov't
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0008-4018
- Country of Publication
- CANADA
Record 24 from database: MEDLINE
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- Title
- Growth inhibitory effects of dimethyl sulfoxide and
dimethyl sulfone on vascular smooth muscle and endothelial
cells in vitro.
- Author
- Layman DL
- Address
-
- Source
- In Vitro Cell Dev Biol, 1987 Jun, 23:6, 422-8
- Abstract
- The growth of bovine aortic smooth muscle and endothelial
cells was studied after exposure to dimethyl sulfoxide
(DMSO) or its major metabolite, dimethyl sulfone (DMSO2).
Both compounds caused a dose-dependent inhibition of cell
growth as determined by [3H]thymidine incorporation and by
counting the number of cells with time of exposure in
culture. The IC50 of DMSO (concentration which produces 50%
inhibition of growth) was 1% for smooth muscle cells and
2.9% for endothelial cells. Similarly, the IC50 of DMSO2 was
also 1% for smooth muscle cells, but was 1.8% for
endothelial cells. After a 4-d exposure to either compound,
the growth inhibition of smooth muscle cells was completely
reversible at 1%, partially reversible at 2 to 3% and
completely irreversible at 4%. By comparison, inhibition of
endothelial cell growth was completely reversible up to 4%
of either compound. It is concluded that the growth of
smooth muscle cells was similarly inhibited by DMSO and
DMSO2, but that smooth muscle cells were more susceptible
than endothelial cells to the growth inhibitory effects of
these compounds. In addition, DMSO2 was a more potent
inhibitor of cell growth than DMSO and its growth inhibition
was less reversible than that produced by DMSO.
- Language of Publication
- English
- Unique Identifier
- 87250195
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- MeSH Heading (Major)
- Dimethyl Sulfoxide|*PD; Endothelium|*CY/DE; Muscle,
Smooth, Vascular|*CY/DE; Sulfones|*PD
- MeSH Heading
- Animal; Aorta; Cattle; Cell Division|DE; Cell Survival|DE;
Cells, Cultured; Time Factors
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0883-8364
- Country of Publication
- UNITED STATES
Record 25 from database: MEDLINE
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- Title
- Cryoprotection by dimethyl sulfoxide and dimethyl sulfone.
- Author
- McGann LE; Walterson ML
- Address
-
- Source
- Cryobiology, 1987 Feb, 24:1, 11-6
- Abstract
- Preservation of cells and tissues at low temperatures
requires the presence of effective cryoprotectants with low
toxicity to which cells are relatively permeable. Two
similar compounds, dimethyl sulfoxide (DMSO) and dimethyl
sulfone (DMSO2), exhibit both features for cryoprotectants,
yet DMSO is a very effective cryoprotectant while DMSO2 is
ineffective. This anomaly was investigated by relating
observations on the phase behavior of DMSO and DMSO2 in
aqueous solutions to the recovery of human lymphocytes
frozen in the presence of these compounds. The lack of
cryoprotection in the presence of DMSO2 appears to be due to
the precipitation of DMSO2 from the solution at subzero
temperatures. The observation of reduced cell recovery after
freezing with increasing concentrations of DMSO2 implies
that cell damage is related to the amount of solid DMSO2
present. Precipitation of DMSO2 occurs both intra- and
extracellularly, but it is argued that intracellular
precipitation of DMSO2 is the damaging phenomenon.
Cryoprotective compounds are normally selected based on the
criteria of low toxicity and permeability to the plasma
membrane. An additional condition, solubility, must be
included for interpretation of experimental data and for
development of effective protocols for cryopreservation.
- Language of Publication
- English
- Unique Identifier
- 87132479
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- MeSH Heading (Major)
- Dimethyl Sulfoxide|*; Lymphocytes|*CY; Sulfones|*; Tissue
Preservation|*MT
- MeSH Heading
- Cell Survival; Freezing; Human; Support, Non-U.S. Gov't
- Publication Type
- JOURNAL ARTICLE
- ISSN
- 0011-2240
- Country of Publication
- UNITED STATES
Record 26 from database: MEDLINE
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- Title
- Subunit associations of (Na+ + K+)-dependent adenosine
triphosphatase. Chemical cross-linking studies.
- Author
- Periyasamy SM; Huang WH; Askari A
- Address
-
- Source
- J Biol Chem, 1983 Aug, 258:16, 9878-85
- Abstract
- Cross-linking reactions of the alpha- and beta-subunits of
the purified membrane-bound enzyme
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