Dihydroabikoviromycin

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Dihydroabikoviromycin
Category Antibiotics
Catalog number BBF-01397
CAS 38704-36-8
Molecular Weight 163.22
Molecular Formula C10H13NO

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Description

It is produced by the strain of Streptomyces olivaceus, Str. reticuli.

Specification

Synonyms 7-Ethylidene-1a alpha,2,3,7-tetrahydrocyclopent(b)oxireno(c)piperiidine
IUPAC Name (10Z)-10-ethylidene-2-oxa-6-azatricyclo[5.3.0.01,3]dec-8-ene
Canonical SMILES CC=C1C=CC2C13C(O3)CCN2
InChI InChI=1S/C10H13NO/c1-2-7-3-4-8-10(7)9(12-10)5-6-11-8/h2-4,8-9,11H,5-6H2,1H3/b7-2-
InChI Key XFDNFSFFQFVZGJ-UQCOIBPSSA-N

Properties

Antibiotic Activity Spectrum viruses
Boiling Point 290.31°C at 760 mmHg
Density 1.05 g/cm3

Reference Reading

1. Genotoxicity of dihydroabikoviromycin, a secondary metabolite of Streptomyces anulatus
J Holmalahti, J Mäki-Paakkanen, L Kangas, A von Wright Mutat Res. 1996 Jul 5;368(3-4):157-63. doi: 10.1016/s0165-1218(96)90057-9.
The potential genotoxicity of dihydroabikoviromycin was assessed in bacterial and sister-chromatid exchange (SCE) test systems. Direct cytotoxicity was also assayed using bioluminescence methods to screen for differences in cell viability among different tumour cell lines following exposure to the drug. Differential killing tests with Escherichia coli WP2 and its repair-deficient derivative CM871 indicated that a functional DNA repair system was protective against the action of dihydroabikoviromycin, implying that this compound causes some form of DNA damage and is almost certainly therefore genotoxic. Dose-dependent reversion from His- to His+ with dihydroabikoviromycin was observed in the Ames test with Salmonella typhimurium TA100, but not in frameshift tester strain TA98. Dihydroabikoviromycin also induced the sfiA gene, as indicated by beta-galactosidase induction in an SOS-chromotest with E. coli PQ37 strain. A dose-related increase in SCEs by dihydroabikoviromycin was observed in CHO cells. Growth of tumour cells was also suppressed by dihydroabikoviromycin at a dose of 10 micrograms/ml.

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