Three-Arm, Biotin-Tagged Carbazole–Dicyanovinyl–Chlorambucil Conjugate: Simultaneous Tumor Targeting, Sensing, and Photoresponsive Anticancer Drug Delivery

Yarra Venkatesh, S. Karthik, Y. Rajesh, Mahitosh Mandal, Avijit Jana, N. D.Pradeep Singh

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

The design, synthesis, and in vitro biological studies of a biotin–carbazole–dicyanovinyl–chlorambucil conjugate (Bio-CBZ-DCV-CBL; 6) are reported. This conjugate (6) is a multifunctional single-molecule appliance composed of a thiol-sensor DCV functionality, a CBZ-derived phototrigger as well as fluorescent reporter, and CBL as the anticancer drug, and Bio as the cancer-targeting ligand. In conjugate 6, the DCV bond undergoes a thiol–ene click reaction at pH<7 with intracellular thiols, thereby shutting down internal charge transfer between the donor CBZ and acceptor DCV units, resulting in a change of the fluorescence color from green to blue, and thereby, sensing the tumor microenvironment. Subsequent photoirradiation results in release of the anticancer drug CBL in a controlled manner.

Original languageEnglish (US)
Pages (from-to)3482-3486
Number of pages5
JournalChemistry - An Asian Journal
Volume11
Issue number24
DOIs
StatePublished - Dec 19 2016
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

Keywords

  • antitumor agents
  • cancer
  • drug delivery
  • glutathione sensing
  • photochemistry

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