Synthesis and antitumor activity of novel 3-oxo-23-hydroxybetulinic acid derivatives

Hengyuan Zhang; Peiqing Zhu; Jie Liu; Xue Yang; Shengtao Xu; Hequan Yao; Jieyun Jiang; Wencai Ye; Xiaoming Wu; Jinyi Xu

doi:10.1016/j.ejmech.2014.09.058

Synthesis and antitumor activity of novel 3-oxo-23-hydroxybetulinic acid derivatives

Hengyuan Zhang
, Peiqing Zhu
, Jie Liu
, Xue Yang
, Shengtao Xu
, Hequan Yao
, Jieyun Jiang
, Wencai Ye
, Xiaoming Wu
, Jinyi Xu

Microbiology, Immunology, and Molecular Genetics

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

21 Scopus citations

Abstract

A series of novel derivatives of 3-oxo-23-hydroxybetulinic acid was designed, synthesized, and evaluated for their antiproliferative activity against a panel of cancer cell lines (HL-60, BEL-7402, SF-763, HeLa, B16 and A375). The results indicated that majority of the derivatives exhibited more significant antitumor activity than the parent compound. In particular compound 10e showed the most potent activity with IC₅₀values of 5.85, 6.23 and 7.22 μM against B16, SF-763 and BEL-7402 cells, respectively. Furthermore, 10e inhibited tumor growth by 51.8% and 62.7% (w/w) in H22 and B16 xenograft mouse models, comparable to cyclophosphamide and 5-fluorouracil, respectively.

Original language	English
Pages (from-to)	159-167
Number of pages	9
Journal	European Journal of Medicinal Chemistry
Volume	87
DOIs	https://doi.org/10.1016/j.ejmech.2014.09.058
State	Published - Nov 24 2014

Bibliographical note

Publisher Copyright:
© 2014 Elsevier Masson SAS.

Funding

The project was funded by the National Natural Science Foundation of China (No. 81273377 ), Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University), Ministry of Education of China (No. CMEMR2013-B05 ), the Project for Research and Innovation of Graduates in Universities of Jiangsu Province ( CXLX13_306 ) and the Project Program of State Key Laboratory of Natural Medicines, China Pharmaceutical University (No. SKLNMZZCX201404 ).

Funders	Funder number
Project for Research and Innovation of Graduates in Universities of Jiangsu Province	CXLX13_306
National Natural Science Foundation of China (NSFC)	81273377
Ministry of Education of the People's Republic of China	CMEMR2013-B05
Guangxi Normal University
State Key Laboratory of Natural Medicines, China Pharmaceutical University	SKLNMZZCX201404
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources

Keywords

3-Oxo-23-hydroxybetulinic acid
Antiproliferative activity
Antitumor activity
B16 melanoma
Chemical modification

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.ejmech.2014.09.058

Cite this

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title = "Synthesis and antitumor activity of novel 3-oxo-23-hydroxybetulinic acid derivatives",

abstract = "A series of novel derivatives of 3-oxo-23-hydroxybetulinic acid was designed, synthesized, and evaluated for their antiproliferative activity against a panel of cancer cell lines (HL-60, BEL-7402, SF-763, HeLa, B16 and A375). The results indicated that majority of the derivatives exhibited more significant antitumor activity than the parent compound. In particular compound 10e showed the most potent activity with IC50values of 5.85, 6.23 and 7.22 μM against B16, SF-763 and BEL-7402 cells, respectively. Furthermore, 10e inhibited tumor growth by 51.8\% and 62.7\% (w/w) in H22 and B16 xenograft mouse models, comparable to cyclophosphamide and 5-fluorouracil, respectively.",

keywords = "3-Oxo-23-hydroxybetulinic acid, Antiproliferative activity, Antitumor activity, B16 melanoma, Chemical modification",

author = "Hengyuan Zhang and Peiqing Zhu and Jie Liu and Xue Yang and Shengtao Xu and Hequan Yao and Jieyun Jiang and Wencai Ye and Xiaoming Wu and Jinyi Xu",

note = "Publisher Copyright: {\textcopyright} 2014 Elsevier Masson SAS.",

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doi = "10.1016/j.ejmech.2014.09.058",

language = "English",

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AU - Zhang, Hengyuan

AU - Zhu, Peiqing

AU - Liu, Jie

AU - Yang, Xue

AU - Xu, Shengtao

AU - Yao, Hequan

AU - Jiang, Jieyun

AU - Ye, Wencai

AU - Wu, Xiaoming

AU - Xu, Jinyi

PY - 2014/11/24

Y1 - 2014/11/24

N2 - A series of novel derivatives of 3-oxo-23-hydroxybetulinic acid was designed, synthesized, and evaluated for their antiproliferative activity against a panel of cancer cell lines (HL-60, BEL-7402, SF-763, HeLa, B16 and A375). The results indicated that majority of the derivatives exhibited more significant antitumor activity than the parent compound. In particular compound 10e showed the most potent activity with IC50values of 5.85, 6.23 and 7.22 μM against B16, SF-763 and BEL-7402 cells, respectively. Furthermore, 10e inhibited tumor growth by 51.8% and 62.7% (w/w) in H22 and B16 xenograft mouse models, comparable to cyclophosphamide and 5-fluorouracil, respectively.

AB - A series of novel derivatives of 3-oxo-23-hydroxybetulinic acid was designed, synthesized, and evaluated for their antiproliferative activity against a panel of cancer cell lines (HL-60, BEL-7402, SF-763, HeLa, B16 and A375). The results indicated that majority of the derivatives exhibited more significant antitumor activity than the parent compound. In particular compound 10e showed the most potent activity with IC50values of 5.85, 6.23 and 7.22 μM against B16, SF-763 and BEL-7402 cells, respectively. Furthermore, 10e inhibited tumor growth by 51.8% and 62.7% (w/w) in H22 and B16 xenograft mouse models, comparable to cyclophosphamide and 5-fluorouracil, respectively.

KW - 3-Oxo-23-hydroxybetulinic acid

KW - Antiproliferative activity

KW - Antitumor activity

KW - B16 melanoma

KW - Chemical modification

UR - https://www.scopus.com/pages/publications/84907575885

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DO - 10.1016/j.ejmech.2014.09.058

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SN - 0223-5234

VL - 87

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JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

ER -

Synthesis and antitumor activity of novel 3-oxo-23-hydroxybetulinic acid derivatives

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

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Cite this