Release Time:2019-03-11  Hits:

Indexed by: Journal Article

Date of Publication: 2017-12-07

Journal: NEW JOURNAL OF CHEMISTRY

Included Journals: SCIE

Volume: 41

Issue: 23

Page Number: 14279-14287

ISSN: 1144-0546

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 p-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 mu M, respectively) compared with chlorin e6 (IC50 = 28.9 +/- 1.2 mu M). The enhanced cellular uptake and reactive oxygen species (ROS) production of modified chlorins were found to be responsible for their increased in vitro phototoxicity.