Synthesis of a fluorescent photoaffinity probe of OSW-1 by site-selective acylation of an inactive congener and biological evaluation

K Sakurai; M Hiraizumi; N Isogai; R Komatsu; T Shibata; Y Ohta

doi:10.1039/c6cc08955k

Synthesis of a fluorescent photoaffinity probe of OSW-1 by site-selective acylation of an inactive congener and biological evaluation

Chem Commun (Camb). 2017 Jan 3;53(3):517-520. doi: 10.1039/c6cc08955k.

Authors

K Sakurai¹, M Hiraizumi¹, N Isogai¹, R Komatsu¹, T Shibata¹, Y Ohta¹

Affiliation

¹ Tokyo University of Agriculture and Technology, Department of Biotechnology and Life Science, Koganei-shi, Tokyo 184-8588, Japan. sakuraik@cc.tuat.ac.jp.

PMID: 27909709
DOI: 10.1039/c6cc08955k

Abstract

A novel fluorescent photoaffinity probe of OSW-1 was prepared in two steps from a naturally occurring inactive congener by a sequential site-selective acylation strategy using Me₂SnCl₂. It displayed highly potent anticancer activity and a similar intracellular localization property to that of a fluorescently-tagged OSW-1, thereby demonstrating its potential utility in live cell studies.

Publication types

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

MeSH terms

Acylation
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / pharmacokinetics
Antineoplastic Agents / pharmacology
Cell Proliferation / drug effects
Cholestenones / chemical synthesis*
Cholestenones / pharmacokinetics
Cholestenones / pharmacology
Fluorescent Dyes / chemical synthesis*
Fluorescent Dyes / pharmacokinetics
Fluorescent Dyes / pharmacology
HeLa Cells
Humans
Neoplasms / drug therapy
Photoaffinity Labels / chemical synthesis*
Photoaffinity Labels / pharmacokinetics
Photoaffinity Labels / pharmacology
Saponins / chemical synthesis*
Saponins / pharmacokinetics
Saponins / pharmacology

Substances

Antineoplastic Agents
Cholestenones
Fluorescent Dyes
Photoaffinity Labels
Saponins
OSW 1