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Acivicin is a fermentation product of Streptomyces; it is a glutamine analog. Acivicin inhibits γ-glutamyl transferase, CTP synthetase, GMP synthetase, and FGAM synthetase, preventing purine synthesis. Acivicin exhibits anticancer and antifungal activity, although its potential chemotherapeutic benefit is limited by high CNS toxicity. Acivicin inhibits the growth of pancreatic cancer cells and, separately, the growth of Alternaria, Magnaporthe, and Botrytis.
| Cas No. | 42228-92-2 |
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| Purity | ≥98% |
| Formula | C5H7ClN2O3 |
| Formula Wt. | 178.57 g/mol |
| Chemical Name | (2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid |
| IUPAC Name | (2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid |
| Synonym | α-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid, ACIA |
| Melting Point | 209-211°C |
| Solubility | Soluble in water to 18mg/mL. Slightly soluble in methanol, ethanol or chloroform. |
| Appearance | White to off white powder |
| Store Temp | -20°C |
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| Ship Temp | Ambient |
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Maeda K, Nakajima Y, Motoyama T, et al. Effects of acivicin on growth, mycotoxin production and virulence of phytopathogenic fungi. Lett Appl Microbiol. 2014 May 27. [Epub ahead of print]. PMID: 24863673.
Hidalgo M, Rodriguez G, Kuhn JG, et al. Clin Cancer Res. 1998 Nov;4(11):2763-70. PMID: 9829740.
Lyons SD, Sant ME, Christopherson RI. Cytotoxic mechanisms of glutamine antagonists in mouse L1210 leukemia. J Biol Chem. 1990 Jul 5;265(19):11377-81. PMID: 2358467.
Allen L, Meck R, Yunis A. The inhibition of gamma-glutamyl transpeptidase from human pancreatic carcinoma cells by (alpha S,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid (AT-125; NSC-163501). Res Commun Chem Pathol Pharmacol. 1980 Jan;27(1):175-82. PMID: 6102405.