Insights into the structure-activity relationship of the anticancer compound ZJ-101: A critical role played by the cyclohexene ring

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

doi:10.1016/j.bmcl.2016.04.044

Insights into the structure-activity relationship of the anticancer compound ZJ-101: A critical role played by the cyclohexene ring

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

School of Medicine

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

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, a new analog ZJ-102 was designed and synthesized to probe the importance of the cyclohexenyl group through its replacement to a phenyl group using a concise and convergent synthetic approach. The biological evaluation showed that this new analog ZJ-102 is significantly less active against cancer cells in vitro than ZJ-101, suggesting that the cyclohexenyl ring (along with its two stereogenic centers) present in ZJ-101 is important for its anticancer activity.

Original language	English (US)
Pages (from-to)	2890-2892
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	26
Issue number	12
DOIs	https://doi.org/10.1016/j.bmcl.2016.04.044
State	Published - Jun 15 2016

Keywords

Anticancer agent
Asymmetric synthesis
Drug design
Structure-activity relationship
Superstolide A analog

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2016.04.044

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title = "Insights into the structure-activity relationship of the anticancer compound ZJ-101: A critical role played by the cyclohexene ring",

abstract = "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, a new analog ZJ-102 was designed and synthesized to probe the importance of the cyclohexenyl group through its replacement to a phenyl group using a concise and convergent synthetic approach. The biological evaluation showed that this new analog ZJ-102 is significantly less active against cancer cells in vitro than ZJ-101, suggesting that the cyclohexenyl ring (along with its two stereogenic centers) present in ZJ-101 is important for its anticancer activity.",

keywords = "Anticancer agent, Asymmetric synthesis, Drug design, Structure-activity relationship, Superstolide A analog",

author = "Shah, {Aashay K.} and Shan Qian and Dawei Zhang and Head, {Sarah A.} and Liu, {Jun O.} and Zhendong Jin",

note = "Funding Information: This work was made possible by the generous support of the GAP funding from the Office of the Vice President for Research and Economic Development (OVPRED) at the University of Iowa and funding from InnoBioPharma, LLC ( D2015070002 ). Aashay K. Shah was supported by a fellowship from the University of Iowa Center for Biocatalysis and Bioprocessing , and by activities of the Predoctoral Training program in Biotechnology, NIH grant 2T32GM008365 . Special thanks are due to the Graduate College and College of Pharmacy at the University of Iowa for providing a dissertation fellowship to Aashay K. Shah. Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd. All rights reserved.",

year = "2016",

month = jun,

day = "15",

doi = "10.1016/j.bmcl.2016.04.044",

language = "English (US)",

volume = "26",

pages = "2890--2892",

journal = "Bioorganic and Medicinal Chemistry Letters",

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number = "12",

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T1 - Insights into the structure-activity relationship of the anticancer compound ZJ-101

T2 - A critical role played by the cyclohexene ring

AU - Shah, Aashay K.

AU - Qian, Shan

AU - Zhang, Dawei

AU - Head, Sarah A.

AU - Liu, Jun O.

AU - Jin, Zhendong

N1 - Funding Information: This work was made possible by the generous support of the GAP funding from the Office of the Vice President for Research and Economic Development (OVPRED) at the University of Iowa and funding from InnoBioPharma, LLC ( D2015070002 ). Aashay K. Shah was supported by a fellowship from the University of Iowa Center for Biocatalysis and Bioprocessing , and by activities of the Predoctoral Training program in Biotechnology, NIH grant 2T32GM008365 . Special thanks are due to the Graduate College and College of Pharmacy at the University of Iowa for providing a dissertation fellowship to Aashay K. Shah. Publisher Copyright: © 2016 Elsevier Ltd. All rights reserved.

PY - 2016/6/15

Y1 - 2016/6/15

N2 - 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, a new analog ZJ-102 was designed and synthesized to probe the importance of the cyclohexenyl group through its replacement to a phenyl group using a concise and convergent synthetic approach. The biological evaluation showed that this new analog ZJ-102 is significantly less active against cancer cells in vitro than ZJ-101, suggesting that the cyclohexenyl ring (along with its two stereogenic centers) present in ZJ-101 is important for its anticancer activity.

AB - 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, a new analog ZJ-102 was designed and synthesized to probe the importance of the cyclohexenyl group through its replacement to a phenyl group using a concise and convergent synthetic approach. The biological evaluation showed that this new analog ZJ-102 is significantly less active against cancer cells in vitro than ZJ-101, suggesting that the cyclohexenyl ring (along with its two stereogenic centers) present in ZJ-101 is important for its anticancer activity.

KW - Anticancer agent

KW - Asymmetric synthesis

KW - Drug design

KW - Structure-activity relationship

KW - Superstolide A analog

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Insights into the structure-activity relationship of the anticancer compound ZJ-101: A critical role played by the cyclohexene ring

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Keywords

ASJC Scopus subject areas

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