Discovering novel quercetin-3-O-amino acid-esters as a new class of Src tyrosine kinase inhibitors

He Huang; Qi Jia; Jingui Ma; Guangrong Qin; Yingyi Chen; Yonghua Xi; Liping Lin; Weiliang Zhu; Jian Ding; Hualiang Jiang; Hong Liu

doi:10.1016/j.ejmech.2008.09.051

Discovering novel quercetin-3-O-amino acid-esters as a new class of Src tyrosine kinase inhibitors

He Huang
, Qi Jia
, Jingui Ma
, Guangrong Qin
, Yingyi Chen
, Yonghua Xi
, Liping Lin
, Weiliang Zhu
, Jian Ding
, Hualiang Jiang
, Hong Liu

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

39 Scopus citations

Abstract

Quercetin-3-O-amino acid-esters, a new type of quercetin derivatives, were successfully prepared for the first time. Different from quercetin, the novel compounds show higher selectivity as inhibitors against Src tyrosine kinase (IC₅₀ values ranging from 3.2 μM to 9.9 μM) than against EGFR tyrosine kinase. Molecular docking reveals that both hydrophobic and hydrogen bonding interactions are important to the selectivity. Therefore, this study provides a new promising scaffold for further development of new anticancer drugs targeting Src tyrosine kinase.

Original language	English
Pages (from-to)	1982-1988
Number of pages	7
Journal	European Journal of Medicinal Chemistry
Volume	44
Issue number	5
DOIs	https://doi.org/10.1016/j.ejmech.2008.09.051
State	Published - May 2009
Externally published	Yes

Keywords

Amino acid
EGFR
Inhibitor
Quercetin
Src

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10.1016/j.ejmech.2008.09.051

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title = "Discovering novel quercetin-3-O-amino acid-esters as a new class of Src tyrosine kinase inhibitors",

abstract = "Quercetin-3-O-amino acid-esters, a new type of quercetin derivatives, were successfully prepared for the first time. Different from quercetin, the novel compounds show higher selectivity as inhibitors against Src tyrosine kinase (IC50 values ranging from 3.2 μM to 9.9 μM) than against EGFR tyrosine kinase. Molecular docking reveals that both hydrophobic and hydrogen bonding interactions are important to the selectivity. Therefore, this study provides a new promising scaffold for further development of new anticancer drugs targeting Src tyrosine kinase.",

keywords = "Amino acid, EGFR, Inhibitor, Quercetin, Src",

author = "He Huang and Qi Jia and Jingui Ma and Guangrong Qin and Yingyi Chen and Yonghua Xi and Liping Lin and Weiliang Zhu and Jian Ding and Hualiang Jiang and Hong Liu",

note = "Funding Information: We gratefully acknowledge financial support from the State Key Program of Basic Research of China (Grant 2006BAI01B02), the National Natural Science Foundation of China (Grants 20721003 and 20872153), the 863 Hi-Tech Program of China (Grants 2006AA020602, 2006AA02Z336), and 973 program (Grant 2004CB518901). ",

year = "2009",

month = may,

doi = "10.1016/j.ejmech.2008.09.051",

language = "English",

volume = "44",

pages = "1982--1988",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier Masson s.r.l.",

number = "5",

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T1 - Discovering novel quercetin-3-O-amino acid-esters as a new class of Src tyrosine kinase inhibitors

AU - Huang, He

AU - Jia, Qi

AU - Ma, Jingui

AU - Qin, Guangrong

AU - Chen, Yingyi

AU - Xi, Yonghua

AU - Lin, Liping

AU - Zhu, Weiliang

AU - Ding, Jian

AU - Jiang, Hualiang

AU - Liu, Hong

N1 - Funding Information: We gratefully acknowledge financial support from the State Key Program of Basic Research of China (Grant 2006BAI01B02), the National Natural Science Foundation of China (Grants 20721003 and 20872153), the 863 Hi-Tech Program of China (Grants 2006AA020602, 2006AA02Z336), and 973 program (Grant 2004CB518901).

PY - 2009/5

Y1 - 2009/5

N2 - Quercetin-3-O-amino acid-esters, a new type of quercetin derivatives, were successfully prepared for the first time. Different from quercetin, the novel compounds show higher selectivity as inhibitors against Src tyrosine kinase (IC50 values ranging from 3.2 μM to 9.9 μM) than against EGFR tyrosine kinase. Molecular docking reveals that both hydrophobic and hydrogen bonding interactions are important to the selectivity. Therefore, this study provides a new promising scaffold for further development of new anticancer drugs targeting Src tyrosine kinase.

AB - Quercetin-3-O-amino acid-esters, a new type of quercetin derivatives, were successfully prepared for the first time. Different from quercetin, the novel compounds show higher selectivity as inhibitors against Src tyrosine kinase (IC50 values ranging from 3.2 μM to 9.9 μM) than against EGFR tyrosine kinase. Molecular docking reveals that both hydrophobic and hydrogen bonding interactions are important to the selectivity. Therefore, this study provides a new promising scaffold for further development of new anticancer drugs targeting Src tyrosine kinase.

KW - Amino acid

KW - EGFR

KW - Inhibitor

KW - Quercetin

KW - Src

UR - https://www.scopus.com/pages/publications/62549104849

U2 - 10.1016/j.ejmech.2008.09.051

DO - 10.1016/j.ejmech.2008.09.051

M3 - Article

C2 - 19041163

AN - SCOPUS:62549104849

SN - 0223-5234

VL - 44

SP - 1982

EP - 1988

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 5

ER -

Discovering novel quercetin-3-O-amino acid-esters as a new class of Src tyrosine kinase inhibitors

Abstract

Keywords

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