Fluorophore-appended steroidal saponin (dioscin and polyphyllin D) derivatives

Zhiqi Yang; Ella Lai-Ming Wong; Tina Yuen-Ting Shum; Chi-Ming Che; Yongzheng Hui

doi:10.1021/ol0475616

Fluorophore-appended steroidal saponin (dioscin and polyphyllin D) derivatives

Org Lett. 2005 Feb 17;7(4):669-72. doi: 10.1021/ol0475616.

Authors

Zhiqi Yang¹, Ella Lai-Ming Wong, Tina Yuen-Ting Shum, Chi-Ming Che, Yongzheng Hui

Affiliation

¹ Shanghai-Hong Kong Joint Laboratory on Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.

PMID: 15704921
DOI: 10.1021/ol0475616

Abstract

The synthesis of three fluorophore-appended derivatives of dioscin and polyphyllin D is reported herein. Starting from trillin, dansyl derivatives A-C were prepared in overall yields of 7-12% over 7-10 steps. A study of their behavior in a variety of polar solvents suggests that dansyl derivatives A-C are capable of micellar self-assembly and can maintain cytotoxicities (IC50 = 15-18 muM) against the HeLa carcinoma cell line evaluated by standard MTT assay. [structure: see text]

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Conformation
Cell Survival / drug effects
Diosgenin / analogs & derivatives*
Diosgenin / chemical synthesis
Diosgenin / chemistry
Diosgenin / toxicity
Fluorides*
Glycosylation
HeLa Cells
Humans
Models, Molecular
Saponins / chemical synthesis
Saponins / chemistry*
Steroids / chemical synthesis
Trisaccharides / chemistry

Substances

Saponins
Steroids
Trisaccharides
polyphyllin D
dioscin
Diosgenin
Fluorides