Synthesis and Cytotoxic Activity of Novel Betulin Derivatives Containing Hydrazide-Hydrazone Moieties

被引：5

作者：

Wu, Jiale ^{[1
]}

Wang, Jiafeng ^{[1
]}

Han, Yinglong ^{[1
]}

Lin, Yu ^{[1
]}

Wang, Jing ^{[1
]}

Bu, Ming ^{[1
]}

机构：

[1] Qiqihar Med Univ, Coll Pharm, Qiqihar 161006, Peoples R China

来源：

NATURAL PRODUCT COMMUNICATIONS | 2021年 / 16卷 / 10期

关键词：

betulin; hydrazide; hydrazone; derivatives; antitumor activity; ANALOGS; ACID; TETRAHYDROCURCUMIN; AGENTS;

D O I：

10.1177/1934578X211055345

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of novel betulin derivatives containing hydrazide-hydrazone moieties were synthesized. All compounds were evaluated for their cytotoxicity against four human carcinoma cell lines (HepG2, A549, MCF-7 and HCT-116) and a normal human gastric epithelial cell line (GES-1). Among them, compound 6i was the most potent against HepG2 and MCF-7 cell lines, with IC50 values of 9.27 and 8.87 mu M, respectively. The results suggest that the incorporation of a hydrazide-hydrazone side chain at the C-28 position of betulin is beneficial for compounds to display significant cytotoxicity. Compound 6i may be used as a promising skeleton for antitumor agents with improved efficacy.

引用

页数：7

共 40 条

[21] Hypoxia increases the apoptotic response to betulinic acid and betulin in human non-small cell lung cancer cells [J].

Kutkowska, Justyna ;

Strzadala, Leon ;

Rapak, Andrzej .

CHEMICO-BIOLOGICAL INTERACTIONS, 2021, 333

[22] Plant extracts and betulin from Ligaria cuneifolia inhibit P-glycoprotein function in leukemia cells [J].

Laiolo, Jeronimo ;

Barbieri, Cecilia L. ;

Joray, Mariana B. ;

Lanza, Priscila A. ;

Palacios, Sara M. ;

Vera, D. Mariano A. ;

Carpinella, Maria C. .

FOOD AND CHEMICAL TOXICOLOGY, 2021, 147

[23] Biotransformation of betulin by Mucor subtilissimus to discover anti-inflammatory derivatives [J].

Li, Jianlin ;

Jiang, Baocheng ;

Chen, Chen ;

Fan, Boyi ;

Huang, Huilian ;

Chen, Guangtong .

PHYTOCHEMISTRY, 2019, 166

[24] Betulin isolated from Pyrola incarnata Fisch. inhibited lipopolysaccharide (LPS)-induced neuroinflammation with the guidance of computer-aided drug design [J].

Liu, Qian ;

Liu, Jin-Ping ;

Mei, Jia-Hui ;

Li, Shuang-Jun ;

Shi, Li-Qiao ;

Lin, Zong-Hao ;

Xie, Bai-Yan ;

Sun, Wei-Guang ;

Wang, Zhen-Yu ;

Yang, Xi-Liang ;

Zou, Yu ;

Fang, Wei .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2020, 30 (12)

[25] Schiff Bases of Tetrahydrocurcumin as Potential Anticancer Agents [J].

Mahal, Ahmed ;

Wu, Ping ;

Jiang, Zi-Hua ;

Wei, Xiaoyi .

CHEMISTRYSELECT, 2019, 4 (01) :366-369

[26] Synthesis and Cytotoxic Activity of Novel Tetrahydrocurcumin Derivatives Bearing Pyrazole Moiety [J].

Mahal A. ;

Wu P. ;

Jiang Z.-H. ;

Wei X. .

Natural Products and Bioprospecting, 2017, 7 (6) :461-469

[27] In Vitro and In Silico Evaluation of Betulin on Calcium Oxalate Crystal Formation [J].

Nirala, Ranjeet Kumar ;

Dutta, Pratuyasha ;

Malik, Md Zubbair ;

Dwivedi, Lalita ;

Shrivastav, Tulsidas G. ;

Thakur, Sonu Chand .

JOURNAL OF THE AMERICAN COLLEGE OF NUTRITION, 2019, 38 (07) :586-596

[28] Influence of oxidative stress on the antibacterial activity of betulin, betulinic acid and ursolic acid [J].

Oloyede, H. O. B. ;

Ajiboye, H. O. ;

Salawu, M. O. ;

Ajiboye, T. O. .

MICROBIAL PATHOGENESIS, 2017, 111 :338-344

[29] Anti-inflammatory effect and potential mechanism of betulinic acid on λ-carrageenan-induced paw edema in mice [J].

Ou, Zhaoping ;

Zhao, Jing ;

Zhu, Lijuan ;

Huang, Lin ;

Ma, Yurong ;

Ma, Chaoyang ;

Luo, Chenxi ;

Zhu, Zihan ;

Yuan, Zhihang ;

Wu, Jing ;

Li, Rongfang ;

Yi, Jine .

BIOMEDICINE & PHARMACOTHERAPY, 2019, 118

[30] Hydrazide-Hydrazone Small Molecules as AIEgens: Illuminating Mitochondria in Cancer Cells [J].

Patil, Sohan ;

Pandey, Shalini ;

Singh, Amit ;

Radhakrishna, Mithun ;

Basu, Sudipta .

CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (35) :8229-8235

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