Synthesis and structure-activity relationship of botryllamides that block the ABCG2 multidrug transporter.

Bioorganic & Medicinal Chemistry Letters
Kentaro TakadaCurtis J Henrich

Abstract

In previous work, botryllamides discovered from the marine ascidian Botryllus tyreus were characterized as selective inhibitors of the ABCG2 multidrug transporter. However, the structural basis for this activity could not be established. In this study, botryllamide F, the core botryllamide structure, and botryllamide G, the most potent botryllamide ABCG2 inhibitor, were synthesized along with a series of structural variants for evaluation of structure-activity relationships. The biological activity of synthetic botryllamide analogs implied that the 2-methoxy-p-coumaric acid portion, and the degree of double bond conjugation within this group, were critical for inhibition of ABCG2. However, variations in the substituents on the two aryl groups did not appear to significantly impact the potency or degree of inhibition.

References

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Citations

Feb 23, 2011·Marine Drugs·Manickam Sugumaran, William E Robinson
Apr 10, 2015·Marine Drugs·Lilia CherigoSergio Martinez-Luis
Sep 8, 2016·Organic Letters·Mohana Rao VippilaGregory D Cuny
Dec 23, 2016·Medicinal Research Reviews·Diana Peña-SolórzanoCristian Ochoa-Puentes
Jul 12, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Solida LongMadalena M M Pinto
Dec 24, 2011·Natural Product Reports·John W BluntMichèle R Prinsep
Mar 19, 2020·Natural Product Reports·Brice A P WilsonBarry R O'Keefe
May 1, 2014·Molecular Informatics·Floriane Montanari, Gerhard F Ecker
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Nov 12, 2019·Cancer Biology & Therapy·Jonathan D StropeWilliam D Figg
Feb 28, 2020·European Journal of Medicinal Chemistry·Frauke AntoniGünther Bernhardt
Jul 2, 2021·Chemical Reviews·Alberto MassarottiGian Cesare Tron

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