Cited by 1,683Sulfur Compounds in BiologyGlutathione Transferases and PolymorphismsAmino Acid Enzymes and Metabolism

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Potent and specific inhibition of glutathione synthesis by buthionine sulfoximine (S-n-butyl homocysteine sulfoximine).

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Griffith, O.W., Meister, A.·1979·Journal of Biological Chemistry

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Abstract

Buthionine sulfoximine (S-n-butyl homocysteine sulfoximine), the most potent of a series of analogs of methionine sulfoximine thus far studied (Griffith, O.W., Anderson, M.E., and Meister, A. (1979) J. Biol. Chem. 254, 1205-1210), inhibited gamma-glutamylcysteine synthetase about 20 times more effectively than did prothionine sulfoximine and at least 100 times more effectively than methionine sulfoximine. The findings support the conclusion that the S-alkyl moiety of the sulfoximine binds at the enzyme site that normally binds the acceptor amino acid. Thus, the affinity of the enzyme for the S-ethyl, S-n-propyl, and S-n-butyl sulfoximines increases in a manner which is parallel to those of the corresponding isosteric acceptor amino acid substrates, i.e. glycine, alanine, and alpha-aminobutyrate. Buthionine sulfoximine did not inhibit glutamine synthetase detectably, nor did it produce convulsions when injected into mice. Injection of buthionine sulfoximine into mice decreased the level of glutathione in the kidney to a greater extent (less than 20% of the control level) than found previously after giving prothionine sulfoximine. alpha-Methyl buthionine sulfoximine was also prepared and found to be almost as effective as buthionine sulfoximine; this compound would not be expected to undergo substantial degradative metabolism. Buthionine sulfoximine and alpha-methyl buthionine sulfoximine may be useful agents for inhibition of glutathione synthesis in various experimental systems.

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Mechanism of inhibition of glutamine synthetase by methionine sulfoximine
Ronzio, R. A., Rowe, W. B., & Meister, A. (1969) · Biochemistry · doi:10.1021/bi00831a038 · Cited by 327
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Inhibition of glutathione biosynthesis by prothionine sulfoximine (S-n-propyl homocysteine sulfoximine), a selective inhibitor of gamma-glutamylcysteine synthetase.
Griffith, O. W., Anderson, M. E., & Meister, A. (1979) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)34188-1 · Cited by 172
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Identification of L-methionine S-sulfoximine as the diastereoisomer of L-methionine SR-sulfoximine that inhibits glutamine synthetase
Manning, J. M., Moore, S., Rowe, W. B., & Meister, A. (1969) · Biochemistry · doi:10.1021/bi00834a066 · Cited by 166
Self-citation
Phosphorylation of methionine sulfoximine by glutamine synthetase.
Ronzio, R. A., & Meister, A. (1968) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.59.1.164 · Cited by 156
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gamma-Glutamylcysteine synthetase. Further purification, "half of the sites" reactivity, subunits, and specificity.
Sekura, R. D., & Meister, A. (1977) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)40500-x · Cited by 149
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Differential inhibition of glutamine and gamma-glutamylcysteine synthetases by alpha-alkyl analogs of methionine sulfoximine that induce convulsions.
Griffith, O. W., & Meister, A. (1978) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)38077-8 · Cited by 101
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Authors: Griffith, O. W., & Meister, A.
Affiliations: Cornell University (US)
Venue: Journal of Biological Chemistry
Publisher: Elsevier BV
Published: 1979-08
Volume: 254
Issue: 16
Pages: 7558-7560
ISSN: 0021-9258 (ISSN-L)
DOI: 10.1016/s0021-9258(18)35980-5
OpenAlex: W1535828429
Cited by: 1,683
References: 10
Citations by year: 2026: 12 · 2025: 25 · 2024: 33 · 2023: 30 · 2022: 33 · 2021: 34 · 2020: 26 · 2019: 27 · 2018: 28 · 2017: 25 · 2016: 33 · 2015: 35 · 2014: 38 · 2013: 36 · 2012: 29
FWCI: 3.97
Type: journal article
Language: en
Open access: hybrid
doi.org
Licence: cc-by
www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
creativecommons.org/licenses/by/4.0/ (vor, 15044 d)
Locations: Journal of Biological Chemistry (publishedVersion, cc-by)
PubMed (publishedVersion)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Sulfur Compounds in Biology
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Glutathione Transferases and Polymorphisms
Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Amino Acid Enzymes and Metabolism
Keywords: buthionine sulfoximine, glutathione synthesis inhibition, gamma-glutamylcysteine synthetase, enzyme inhibition, glutathione, glutamine synthetase
MeSH terms: Glutamate-Cysteine Ligase, Glutathione, Kinetics, Methionine Sulfoximine, Peptide Synthases, Structure-Activity Relationship

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Potent and specific inhibition of glutathione synthesis by buthionine sulfoximine (S-n-butyl homocysteine sulfoximine).

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