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• W1972504878 abstract "Anthracyclines, such as daunorubicin (DNR) and doxorubicin (Dox), are widely used for cancer therapy but are limited by drug resistance and cardiotoxicity. To overcome drug resistance, we synthesized a novel class of disaccharide analogues of DNR against drug-resistant leukemia. In these disaccharide analogues (1−6) the first (inner) sugar in the carbohydrate chain is a 3-azido-2,3,6-trideoxy-l-lyxo-α-hexopyranose; the second (outer) sugars that are linked via α(1→4) to the first sugar are a series of uncommon sugars. Their cytotoxicities were examined in drug-sensitive leukemia cells K562 and doxorubicin-resistant K562/Dox cells by MTS assay. In drug-sensitive cells, compounds 1−6 were found to be active against leukemia K562 cells with IC50 in the nanomolar range (200−1100 nM), while compounds 2−5 with 2,6-dideoxy sugars showed better activity than compounds 1 and 6 with 2,3,6-trideoxy sugars. In doxorubicin-resistant K562/Dox cells, compounds 1, 3, and 5 exhibited much better activities (with IC50 between 0.29 and 2.0 μM) than DNR (with IC50 > 5 μM). Compound 3 emerged as the most active compound, showing at least 17-fold higher activity against drug-resistant cells than parent compound DNR. The IC50 values of compound 3 in both drug-sensitive and drug-resistant cells are identical, which indicates that compound 3 completely overcomes drug resistance. Structure−activity relationship (SAR) studies showed that the substitution and orientation of the 3-OH group in the second sugar significantly influence its activity against drug-resistant leukemia. These results suggest that sugar modifications of anthracyclines change their activity and overcome drug resistance." @default.
• W1972504878 created "2016-06-24" @default.
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• W1972504878 date "2006-02-02" @default.
• W1972504878 modified "2023-10-18" @default.
• W1972504878 title "Syntheses and Biological Activities of 3‘-Azido Disaccharide Analogues of Daunorubicin against Drug-Resistant Leukemia" @default.
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• W1972504878 doi "https://doi.org/10.1021/jm050916m" @default.
• W1972504878 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/16509594" @default.
• W1972504878 hasPublicationYear "2006" @default.
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