Glucoside Derivatives Of Podophyllotoxin: Synthesis, Physicochemical Properties, And Cytotoxicity
Zi, Cheng-Ting1,2; Yang, Liu2; Kong, Qing-Hua2; Li, Hong-Mei2; Yang, Xing-Zhi2; Ding, Zhong-Tao3; Jiang, Zi-Hua4; Hu, Jiang-Miao2; Zhou, Jun2
Corresponding AuthorJiang, Zi-Hua(zjiang@lakeheadu.ca) ; Hu, Jiang-Miao(hujiangmiao@mail.kib.ac.cn)
2019
Source PublicationDRUG DESIGN DEVELOPMENT AND THERAPY
ISSN1177-8881
Volume13Pages:3683-3692
AbstractBackground: Widespread concern of the side effects and the broad-spectrum anticancer property of podophyllotoxin as an antitumor agent highlight the need for the development of new podophyllotoxin derivatives. Although some per-butyrylated glucosides of podophyllotoxin and 4 beta-triazolyl-podophyllotoxin glycosides show good anticancer activity, the peracetylated/free of podophyllotoxin glucosides and their per-acetylated are not well studied. Methods: A few glucoside derivatives of PPT were synthesized and evaluated for their in vitro cytotoxic activities against five human cancer cell lines, HL-60 (leukemia), SMMC-7721 (hepatoma), A-549 (lung cancer), MCF-7 (breast cancer), and SW480 (colon cancer), as well as the normal human pulmonary epithelial cell line (BEAS-2B). In addition, we investigated the structure-activity relationship and the physicochemical property-anticancer activity relationship of these compounds. Results: Compound 6b shows the highest cytotoxic potency against all five cancer cell lines tested, with IC50 values ranging from 3.27 +/- 0.21 to 11.37 +/- 0.52 mu M. We have also found that 6b displays higher selectivity than the etoposide except in the case of HL-60 cell line. The active compounds possess similar physicochemical properties: MSA > 900, %PSA < 20, ClogP > 2, MW > 700 Da, and RB > 10. Conclusion: We synthesized several glucoside derivatives of PPT and tested their cytotoxicity. Among them, compound 6b showed the highest cytotoxicity. Further studies including selectivity of active compounds have shown that the selectivity indexes of 6b are much greater than the etoposide except in the case of HL-60 cell line. The active compounds possessed similar physicochemical properties. This study indicates that active glucoside analogs of podophyllotoxin have potential as lead compounds for developing novel anticancer agents.
Keywordpodophyllotoxin glucoside synthesis cytotoxicity physicochemical properties
DOI10.2147/DDDT.S215895
Indexed BySCI ; SCI
Language英语
WOS IDWOS:000492143900002
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/70943
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorJiang, Zi-Hua; Hu, Jiang-Miao
Affiliation1.Yunnan Agr Univ, Coll Sci, Key Lab Pu Er Tea Sci, Minist Educ, Kunming 650201, Yunnan, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, 132 Lanhei Rd, Kunming 650201, Yunnan, Peoples R China
3.Yunnan Univ, Sch Chem Sci & Technol, Key Lab Med Chem Nat Resource, Minist Educ, Kunming 650091, Yunnan, Peoples R China
4.Lakehead Univ, Dept Chem, 955 Oliver Rd, Thunder Bay, ON P7B 5E1, Canada
Recommended Citation
GB/T 7714
Zi, Cheng-Ting,Yang, Liu,Kong, Qing-Hua,et al. Glucoside Derivatives Of Podophyllotoxin: Synthesis, Physicochemical Properties, And Cytotoxicity[J]. DRUG DESIGN DEVELOPMENT AND THERAPY,2019,13:3683-3692.
APA Zi, Cheng-Ting.,Yang, Liu.,Kong, Qing-Hua.,Li, Hong-Mei.,Yang, Xing-Zhi.,...&Zhou, Jun.(2019).Glucoside Derivatives Of Podophyllotoxin: Synthesis, Physicochemical Properties, And Cytotoxicity.DRUG DESIGN DEVELOPMENT AND THERAPY,13,3683-3692.
MLA Zi, Cheng-Ting,et al."Glucoside Derivatives Of Podophyllotoxin: Synthesis, Physicochemical Properties, And Cytotoxicity".DRUG DESIGN DEVELOPMENT AND THERAPY 13(2019):3683-3692.
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