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Water-Soluble Heliomycin Derivatives to Target i-Motif DNA.

Tikhomirov, AS; Abdelhamid, MAS; Nadysev, GY; Zatonsky, GV; Bykov, EE; Chueh, PJ; Waller, ZAE; (2021) Water-Soluble Heliomycin Derivatives to Target i-Motif DNA. Journal of Natural Products , 84 (5) pp. 1617-1625. 10.1021/acs.jnatprod.1c00162.

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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.

Type: Article
Title: Water-Soluble Heliomycin Derivatives to Target i-Motif DNA.
Location: United States
DOI: 10.1021/acs.jnatprod.1c00162
Publisher version: https://doi.org/10.1021/acs.jnatprod.1c00162
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
UCL classification: UCL
UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10129349
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