Synthesis and cytotoxicity study of novel 3-(triazolyl)coumarins based fluorescent scaffolds

Bioorg Med Chem Lett. 2016 Nov 15;26(22):5557-5561. doi: 10.1016/j.bmcl.2016.09.078. Epub 2016 Oct 1.

Abstract

Recently a choice of fluorescent bioimaging probes have been developed as medical diagnostic tools. Herein, we have introduced a series of coumarin-based target specific probes for cancer theranostic application which play a dual role in the field of both diagnosis and therapy. A fluorogenic version of 1,3-dipolar cycloaddition between azides and alkynes (DBCO) has been introduced to develop the triazolylcoumarin based fluorescent scaffolds. These scaffolds were screened for their anticancer activity against breast cancer (MCF7) and human epitheloid cervix carcinoma (HeLa) cell line. It was established that triazolylcoumarins (5c and 5d) are having electronegative substitution in the benzene ring displayed most effective anticancer profile in both the cell lines. Compounds 5a and 5d exhibited maximum quantum yield and strong cellular uptake in the MCF-7 cell line.

Keywords: Anticancer activity; Fluorescence imaging; Fluorescence study; Theranostic application; Triazolylcoumarin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Breast Neoplasms / diagnosis
  • Breast Neoplasms / drug therapy
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Coumarins / chemistry
  • Coumarins / pharmacology*
  • Cycloaddition Reaction
  • Female
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology*
  • HeLa Cells
  • Humans
  • MCF-7 Cells
  • Optical Imaging / methods
  • Theranostic Nanomedicine
  • Triazoles / chemistry
  • Triazoles / pharmacology*
  • Uterine Cervical Neoplasms / diagnosis
  • Uterine Cervical Neoplasms / drug therapy

Substances

  • Antineoplastic Agents
  • Coumarins
  • Fluorescent Dyes
  • Triazoles