Bacterial nitroreductase for the reduction of CB1954 and analogu

Details Bacterial nitroreductase for the reduction of CB1954 and analogu Bacterial nitroreductase for the reduction of CB1954 and analogu

1998-06-01

1999-11-02

Davenport, Avis M.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

514 11, 530317, A61K 3800, A61K 3812, C07K 500, C07K 700

Patent

active

059770651

ABSTRACT:
A prodrug of the formula (I): ##STR1## where R.sup.1 is a group such that the compound R.sup.1 NH.sub.2 represents actinomycin D, doxorubicin, mitomycin C, or a nitrogen mustard of the formula (IV): ##STR2## a prodrug of the formula (II): ##STR3## where R.sup.2 is a group such that the compound R.sup.2 OH is a phenolic nitrogen mustard; and processes whereby the prodrugs shown above are made in which a prodrug precursor compound is reacted with 4-nitrobenzyl chloroformate under anhydrous conditions.

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patent: 4868303 (1989-09-01), Takase et al.
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McCalla, D.R., . et al., Nitrofurazone-reducing enzymes in E. coli and their role n drug activation in vivo, Can. J. Microbiol., vol. 1, pp. 1484-1491, (1975).
Knox, R.J., et al., "The Nitroreductase Enzyme in Walker Cells That Activates 5-(Aziridin-1-YL)-2,4-Dinitrobenzamide (CB!1954) to 5-(Aziridin-1-YL)-4-hydroxylamino-2-nitrobenzamidin is a form of NAD (P) H Dehydrogenase (Quinone) (EC.1.6.99.2)", Biochem. Pharmacol., vol. 37, pp. 4671-4677, (1988).
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Bryant, Christopher et al., "Cloning, Nucleotide Sequence, and Expression of the Nitroreductase Gene from Enterbacter cloacae", Journal of Biological Chemistry, vol. 266, No. 7, pp. 4126-4130 (Mar. 1991).
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Chemical Abstracts, vol. 95, Abstract No. 98201a (1981), Mikhailopulo, I.A. et al., "Synthesis of glycosides of nicotinamide and nicotinamide mononucleotide.".
Knox, Richard J., "A New Cytotoxic, DNA Interstrand Crosslinking Agent, 5-(Aziridin-1-YL)-4-Hydroxylamino-2-Nitrobenzamide, is Formed From 5-(Azirdin-1-YL)-2,4-in Walker Carcinoma Calls", Biochemical Pharmacology, vol. 37, No. 24, pp. 4661-4669 (1988).

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