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Methionine sulfoximine information


l-Methionine sulfoximine
Names
IUPAC name
(2S)-2-Amino-4-(S-methylsulfonimidoyl)butanoic acid
Other names
l-Methionine sulfoximine; MSO
Identifiers
CAS Number
  • 15985-39-4 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
1725509
ChEBI
  • CHEBI:28490
ChemSpider
  • 80339
ECHA InfoCard 100.016.224 Edit this at Wikidata
EC Number
  • 217-845-8
PubChem CID
  • 89034
UNII
  • M9P6YZ6JX9 checkY
InChI
  • InChI=1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)/t4-,11?/m0/s1
    Key: SXTAYKAGBXMACB-DPVSGNNYSA-N
SMILES
  • CS(=N)(=O)CC[C@@H](C(=O)O)N
Properties
Chemical formula
C5H12N2O3S
Molar mass 180.22 g·mol−1
Related compounds
Related compounds
Buthionine sulfoximine
Glufosinate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methionine sulfoximine (MSO, also known as MetSox[1]) is an irreversible glutamine synthetase inhibitor. It is the sulfoximine derivative of methionine with convulsant effects.[2]

Methionine sulfoximine is composed of two different diastereomers, which are L-S-Methionine sulfoximine and L-R-Methionine sulfoximine. These affect the longevity of the model mouse for Lou Gehrig's disease.[3] Overproduction of glutamate results to excitotoxicity, which kills the cell. Since methionine sulfoximine inhibits glutamate production in the brain, it prevents excitotoxicity. Thus, increasing the longevity of the mice.[4]

  1. ^ Carroll, P.; Waddell, S. J.; Butcher, P. D.; Parish, T. (2011). "Methionine sulfoximine resistance in Mycobacterium tuberculosis is due to a single nucleotide deletion resulting in increased expression of the major glutamine synthetase, GlnA1". Microbial Drug Resistance. 17 (3): 351–355. doi:10.1089/mdr.2010.0125. PMC 3161625. PMID 21875360.
  2. ^ Rowe, WB; Meister, A (June 1970). "Identification of L-methionine-S-sulfoximine as the convulsant isomer of methionine sulfoximine". Proceedings of the National Academy of Sciences of the United States of America. 66 (2): 500–6. Bibcode:1970PNAS...66..500R. doi:10.1073/pnas.66.2.500. PMC 283073. PMID 4393740.
  3. ^ Brusilow, William S. A. (2017-04-24). "Identification of the isomer of methionine sulfoximine that extends the lifespan of the SOD1 G93A mouse". Neuroscience Letters. 647: 165–167. doi:10.1016/j.neulet.2017.03.029. ISSN 0304-3940. PMID 28323087. S2CID 45664203.
  4. ^ Bame, Monica; Pentiak, Patricia A.; Needleman, Richard; Brusilow, William S. A. (2012-12-01). "Effect of Sex on Lifespan, Disease Progression, and the Response to Methionine Sulfoximine in the SOD1 G93A Mouse Model for ALS". Gender Medicine. 9 (6): 524–535. doi:10.1016/j.genm.2012.10.014. ISSN 1550-8579. PMID 23217569.

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Alanine transaminase

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Glutamine synthetase

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while low concentrations should activate GS activity. Inhibitors: Methionine sulfoximine (MSO): MSO is an inhibitor that binds to the glutamate site. Bound...

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Theanine

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Guanosine triphosphate

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Organosulfur chemistry

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class of compounds is derived from the discovery that methionine sulfoximide (methionine sulfoximine) is an inhibitor of glutamine synthetase. Sulfonediimines...

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Epigallocatechin gallate

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Furosemide

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Glutamate decarboxylase

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Aspartic acid

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to several amino acids, including four that are essential for humans: methionine, threonine, isoleucine, and lysine. The conversion of aspartate to these...

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Glutamic acid

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Cerebral edema

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conjunction with a rapid rise in ammonia levels. Toxic exposures to methionine sulfoximine, cuprizone, isoniazid, triethyltin, hexachlorophene, and hydrogen...

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Chloroquine

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Rose bengal

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Glufosinate

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Trypan blue

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MSO

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Glutamate dehydrogenase

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Valinomycin

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Glutamate transporter

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Glutaminase

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Vesicular glutamate transporter 1

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Sulfilimine

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include S,S-diphenylsulfilimine and sulfoximines [Category] such as methylphenylsulfoximine: In the case of a sulfoximine, the bonds can be considered single...

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Cycloserine

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Kynurenic acid

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