Adriamycin analogs. 1. Preparation and antitumor evaluation of 7-O-(.beta.-D-glucosaminyl)daunomycinone and 7-O-(.beta.-D-glucosaminyl)adriamycinone and their N-trifluoroacetyl derivatives
- 1 January 1982
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 25 (1) , 24-28
- https://doi.org/10.1021/jm00343a005
Abstract
The title compounds were prepared by Koenigs-Knorr condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-[(trifluoroacetyl)amino]-.alpha.-D-glucopyranosyl bromide with daunomycinone or a side-chain protected adriamycinone, followed by selective hydrolysis of blocking groups. Despite poor complexation with DNA and weak growth-inhibitory properties in vitro, the glucosaminyl analogs of the antitumor antibiotics daunorubicin and adriamycin, at their optimal (highest nontoxic) doses, exhibited antileukemic activity equivalent to that of adriamycin against a usually drug-refractory mouse leukemia model system (L1210) in vivo. These findings, together with other data, continue to support the hypothesis that the mechanism of action of adriamycin and related agents cannot be due exclusively to DNA binding, as has earlier been believed.This publication has 6 references indexed in Scilit:
- N-TRIFLUOROACETYLADRIAMYCIN-14-VALERATE - ADDITIONAL MOUSE ANTI-TUMOR AND TOXICITY STUDIES1978
- URINARY ANTHRACYCLINE METABOLITES FROM MICE TREATED WITH ADRIAMYCIN AND N-TRIFLUOROACETYLADRIAMYCIN-14-VALERATE1978
- HEPATOBILIARY METABOLISM AND EXCRETION OF ADRIAMYCIN AND N-TRIFLUOROACETYLADRIAMYCIN-14-VALERATE IN RAT1978
- COMPARATIVE ANTI-NEOPLASTIC ACTIVITY OF ADRIAMYCIN AND N-TRIFLUOROACETYLADRIAMYCIN-14-VALERATE1978
- AdriamycinAnnals of Internal Medicine, 1974
- The response in vitro, of continuous cultures of human lymphoblasts (CCRF-CEM cells) to chemotherapeutic agentsBiochemical Pharmacology, 1967