Hydroxy acivicin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01569 |
| CAS | 54549-02-9 |
| Molecular Weight | 194.57 |
| Molecular Formula | C5H7ClN2O4 |
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Description
Hydroxy acivicin is an antitumor agent.
Specification
| Synonyms | U 43795; U-43795 |
| IUPAC Name | (2S)-2-amino-2-[(4S,5R)-3-chloro-4-hydroxy-4,5-dihydro-1,2-oxazol-5-yl]acetic acid |
| Canonical SMILES | C1(C(ON=C1Cl)C(C(=O)O)N)O |
| InChI | InChI=1S/C5H7ClN2O4/c6-4-2(9)3(12-8-4)1(7)5(10)11/h1-3,9H,7H2,(H,10,11)/t1-,2-,3+/m0/s1 |
| InChI Key | KUYDILDQEMQBKJ-XZIMBLGRSA-N |
Properties
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
Reference Reading
1. Biochemical pharmacology of acivicin in rat hepatoma cells
M S Lui, H Kizaki, G Weber Biochem Pharmacol. 1982 Nov 1;31(21):3469-73. doi: 10.1016/0006-2952(82)90628-1.
The antiglutamine agent acivicin, L-(alpha S,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid, inhibited the growth of hepatoma 3924A cells in culture. After 7 days of incubation with the drug, an LC50 of 1.4 microM was observed by determination of colony forming ability. A combination of cytidine (1 mM), deoxycytidine (10 microM) and guanosine (10 microM) completely protected the hepatoma cells against the cytotoxic action of acivicin, but each nucleoside by itself had no effect. Acivicin (0.1 mM) inhibited the incorporation of uridine and thymidine into macromolecules, but not that of leucine. Acivicin depressed the pools of CTP, GTP, dCTP, dGTP and dTTP to 46, 62, 40, 64 and 53%, respectively, but it increased UTP level to 152% of the values of untreated cancer cells. The activity of a highly purified CTP synthetase (EC 6.3.4.2) from rat liver and hepatoma 3924A was inhibited by acivicin. The inhibition was competitive with respect to L-glutamine, and the Ki values with liver and hepatoma enzymes, determined by Dixon and reciprocal plots, were 1.1 and 3.6 microM respectively. The hydroxy analog of acivicin was also a competitive inhibitor, but it was less effective than acivicin, with a Ki value of 1.8 mM for the hepatoma enzyme. Our observations on the impact of acivicin on the behavior of pools of ribonucleotides and deoxyribonucleotides and the competitive inhibition of purified CTP synthetase from hepatoma cells suggest that a major mechanism of action for this drug is the inhibition of CTP synthetase and GMP synthetase (EC 6.3.5.2).
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
