Water-Soluble Heliomycin Derivatives to Target i-Motif DNA

Tikhomirov, Alexander S., Abdelhamid, Mahmoud A.S., Nadysev, Georgy Y., Zatonsky, George V., Bykov, Eugene E., Chueh, Pin Ju, Waller, Zoë A.E. and Shchekotikhin, Andrey E. (2021) Water-Soluble Heliomycin Derivatives to Target i-Motif DNA. Journal of Natural Products, 84 (5). pp. 1617-1625. ISSN 0163-3864

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Abstract

Heliomycin (also known as resistomycin) is an antibiotic with a broad spectrum of biological activities. However, low aqueous solubility and poor knowledge of its chemical properties have limited the development of this natural product. Here, we present an original scheme for the introduction of aminoalkylamine residues at positions 3, 5, and 7 of heliomycin and, using this, have prepared a series of novel water-soluble derivatives. The addition of side chains to the heliomycin scaffold significantly improves their interaction with different DNA secondary structures. One derivative, 7-deoxy-7-(2-aminoethyl)amino-10-O-methylheliomycin (8e), demonstrated affinity, stabilization potential, and good selectivity toward i-motif-forming DNA sequences over the duplex and G-quadruplex. Heliomycin derivatives therefore represent promising molecular scaffolds for further development as DNA-i-motif interacting ligands and potential chemotherapeutic agents.

Item Type:	Article
Additional Information:	Publisher Copyright: © 2021 American Chemical Society and American Society of Pharmacognosy.
Uncontrolled Keywords:	analytical chemistry,molecular medicine,pharmacology,pharmaceutical science,drug discovery,complementary and alternative medicine,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1602
Faculty \ School:	Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Related URLs:	https://www.scopus.com/pages/publication...
Depositing User:	LivePure Connector
Date Deposited:	29 Apr 2026 11:18
Last Modified:	30 Apr 2026 14:30
URI:	https://ueaeprints.uea.ac.uk/id/eprint/102831
DOI:	10.1021/acs.jnatprod.1c00162

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