Bioactivation of CB 1954: Reaction of the active 4-hydroxylamino derivative with thioesters to form the ultimate DNA-DNA interstrand crosslinking species

Biochemical Pharmacology

Volumn 42, Issue 9, 1991, Pages 1691-1697

  Knox, Richard J ^a   Friedlos, Frank ^a   Marchbank, Tania ^a   Roberts, John J ^a  

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

5 (1 AZIRIDINYL) 2,4 DINITROBENZAMIDE; 5 (1 AZIRIDINYL) 4 HYDROXYAMINO 2 NITROBENZAMIDE; ACETYL COENZYME A; ACETYLTHIOCHOLINE; ANTINEOPLASTIC AGENT; BUTYRYL COENZYME A; PROPIONYL COENZYME A; RADIOISOTOPE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CATTLE; CONTROLLED STUDY; CYTOTOXICITY; DNA CROSS LINKING; DRUG DNA BINDING; METABOLIC ACTIVATION; NONHUMAN; PRIORITY JOURNAL; THYMUS; TUMOR CELL;

ACETYL COENZYME A; ACETYLTHIOCHOLINE; ANIMAL; AZIRIDINES; BIOTRANSFORMATION; CELL LINE; CROSS-LINKING REAGENTS; DNA; MODELS, CHEMICAL; NAD(P)H DEHYDROGENASE (QUINONE); OXIDATION-REDUCTION; SUPPORT, NON-U.S. GOV'T; TIME FACTORS;

EID: 0026075733     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/0006-2952(91)90503-W     Document Type: Article

References (17)

1. A new cytotoxic, DNA interstrand crosslinking agent, 5-(aziridin- 1- yl)- 4-hydroxylamino- 2-nitrobenzamide, is formed from 5-(aziridin-l-yl)-2,4-dinitrobenzamide (CB 1954) by a nitroreductase enzyme in Walker carcinoma cells
2. The nitroreductase enzyme in Walker cells that activates 5-(aziridin-l-yl)-2,4-dinitrobenz-amide (CB 1954) to 5-(aziridin-l-yl)-4-hydroxyl-amino-2-nitrobenzamideisaform of NAD (P) Hdehydro-genase (quinone) EC 1.6.99.2)
3. The differences in kinetics of rat and human DT diaphorase result in a differential sensitivity of derived cell lines to CB 1954 (5-(aziridin-l-yl)-2,4-dinitrobenzamide)
4. Seryl-t-RNA synthetase and activation of the carcinogen 4-nitroquinoline 1-oxide
5. N-Hydroxy-2-acetyllaminofluorene sulfotransferase: its probable role in carcinogenesis and in protein-(methion-5-yl) binding in rat liver
6. Mechanism of cytotoxicity of anticancer platinum drugs; evidence that cis-diamminedichloroplatinum(II) and cis-diamine-1,1 -cyclobutanedicarboxylato)platinum(II) differ only in the kinetics of their interaction with DNA
7. Quantitative estimation of cisplatin-induced DNA interstrand cross-links and their repair in mammalian cells: relationship to toxicity
8. 2,4-Dinitro-5-ethyleneiminobenzamide (CB 1954): a potent and selective inhibitor of the growth of the Walker carcinoma 256
9. CB 1954 revisited I. Disposition kinetics and metabolism
10. CB 1954 revisited II. Toxicity and antitumour activity
11. Metabolic activation of 4-nitroquinoline 1-oxide and its binding to nucleic acid
12. Metabolic activation of 2-acetylaminofluorene
13. Mechanisms of reaction, tissue distribution, and inhibition of arylhydroxamic acid acyltransferase
14. The metabolism of the anti-tumour agent 5-(l-aziridinyl)-2,4-dinitrobenzamide (CB 1954)
15. Adducts from the reaction of O,O'-diacetyl or O-acetyl derivatives of the carcinogen 4-hydroxyaminoquinoline 1-oxide with purine nucleosides
16. The binding of N-hydroxy-2-acetylaminofluorene to DNA and repair of the adducts in primary rat hepatocyte cultures
17. CB 1954 (2,4-dinitro-5-aziridinyl benzamide) becomes a DNA interstrand crosslinking agent in Walker tumour cells