Insights into the structure–activity relationship of the anticancer compound ZJ-101, a derivative of marine natural product superstolide A: A critical role played by the conjugated trienyl lactone moiety

Shan Qian; Aashay K. Shah; Sarah A. Head; Jun O. Liu; Zhendong Jin

doi:10.1016/j.bmcl.2016.06.057

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Insights into the structure–activity relationship of the anticancer compound ZJ-101, a derivative of marine natural product superstolide A: A critical role played by the conjugated trienyl lactone moiety

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Insights into the structure–activity relationship of the anticancer compound ZJ-101, a derivative of marine natural product superstolide A: A critical role played by the conjugated trienyl lactone moiety

Shan Qian, Aashay K. Shah, Sarah A. Head, Jun O. Liu and Zhendong Jin

Bioorganic & medicinal chemistry letters, Vol.26(15), pp.3411-3413

08/01/2016

DOI: 10.1016/j.bmcl.2016.06.057

PMCID: PMC5013146

PMID: 27374243

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https://www.ncbi.nlm.nih.gov/pmc/articles/5013146View

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Abstract

[Display omitted] Compound ZJ-101, a structurally simplified analog of the marine natural product superstolide A, was previously developed in our laboratory. In the subsequent structure–activity relationship study, two new analogs, ZJ-105 and ZJ-106, were designed and synthesized to probe the importance of the conjugated trienyl lactone moiety of the molecule by replacing the C2–C3 double bond in ZJ-101 with a single bond and switching the geometry of the C4–C5 double bond in ZJ-101 from Z to E, respectively. Biological evaluation showed that ZJ-105 completely loses antiproliferative activity whereas ZJ-106 is significantly less active against cancer cells in vitro than ZJ-101, suggesting that the conjugated trienyl lactone moiety of the molecule is critical for its anticancer activity.

Anticancer agent

Asymmetric synthesis

Drug design

Structure–activity relationship

Superstolide A analog

Details

Title: Subtitle: Insights into the structure–activity relationship of the anticancer compound ZJ-101, a derivative of marine natural product superstolide A: A critical role played by the conjugated trienyl lactone moiety
Creators: Shan Qian - University of Iowa
Aashay K. Shah - University of Iowa
Sarah A. Head - Johns Hopkins Medicine
Jun O. Liu - Johns Hopkins Medicine
Zhendong Jin - University of Iowa
Resource Type: Journal article
Publication Details: Bioorganic & medicinal chemistry letters, Vol.26(15), pp.3411-3413
DOI: 10.1016/j.bmcl.2016.06.057
PMID: 27374243
PMCID: PMC5013146
NLM abbreviation: Bioorg Med Chem Lett
ISSN: 0960-894X
eISSN: 1464-3405
Publisher: Elsevier Ltd
Grant note: name: InnoBioPharma; DOI: 10.13039/100012675, name: University of Iowa Center for Biocatalysis and Bioprocessing, award: 2T32GM008365; DOI: 10.13039/100000002, name: NIH
Language: English
Date published: 08/01/2016
Academic Unit: Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
Record Identifier: 9984366024702771

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