Jump to main content
Jump to site search

Issue 23, 2017
Previous Article Next Article

Synthesis and in vitro phototoxicity of novel π-extension derivatives of chlorin e6

Author affiliations

Abstract

Six novel E-32-aryl substituted chlorins (5a–5f) were synthesized via improved regioselective bromination and Suzuki–Miyaura cross-coupling reactions with chlorin e6 (1) as a starting material. All the π-extension photosensitizers 5a–5f exhibited significant bathochromic-shifts (ca. 10 nm) in the far red part of the spectrum called the phototherapeutic window and decreased photobleaching under irradiation of 660 nm light. Moreover, 5a–5f possessed higher phototoxicity in vitro against HepG2 cells (IC50 = 0.73 ± 0.04, 2.33 ± 0.22, 0.78 ± 0.05, 0.50 ± 0.04, 2.25 ± 0.16 and 0.65 ± 0.11 μM, respectively) compared with chlorin e6 (IC50 = 28.9 ± 1.2 μM). The enhanced cellular uptake and reactive oxygen species (ROS) production of modified chlorins were found to be responsible for their increased in vitro phototoxicity.

Graphical abstract: Synthesis and in vitro phototoxicity of novel π-extension derivatives of chlorin e6

Back to tab navigation

Supplementary files

Publication details

The article was received on 30 Aug 2017, accepted on 13 Oct 2017 and first published on 16 Oct 2017


Article type: Paper
DOI: 10.1039/C7NJ03279J
Citation: New J. Chem., 2017,41, 14279-14287
  •   Request permissions

    Synthesis and in vitro phototoxicity of novel π-extension derivatives of chlorin e6

    L. Cao, X. Guo, L. Wang, S. Wang, Y. Li and W. Zhao, New J. Chem., 2017, 41, 14279
    DOI: 10.1039/C7NJ03279J

Search articles by author

Spotlight

Advertisements