Semi-synthesis and PDT activities of a new amphiphilic chlorin derivative

Author(s)

Moritz, Milene N. O. ; Goncalves, Joyce L. S. ; Linares, Irwin A. P. ; Perussi, Janice R. ; de Oliveira, Kleber T.

• Document type: Journal article
• Source: Photodiagnosis and Photodynamic Therapy; v. 17, p. 39-47, MAR 2017.
• Web of Science Citations: 8

Abstract

An amphiphilic chlorin derivative (CHL-T) was prepared from methylpheophorbide a (CHL) and 2-Amino2-(hydroxymethyl)-1,3-propanediol (TRISMA (R)). The new chlorin was compared to other dyes (CHL and Hypericin) in relation to photophysical and photobiological activities in tumor and non-tumor cell lines. Cytotoxicity and cell death target were determined to evaluate the CHL-T efficiency, comparing to the precursor CHL and to the well-known dye hypericin (HY). All of the studied compounds exhibited absorption bands in the therapeutic window and presented a small fluorescence quantum yield compared to the reference dye (rhodamine B). CHL-T was about three times more efficient on singlet oxygen generation than the others photosensitizers. The lipophilicity order of the photosensitizers was CHL> HY > CHL-T. The tumoral HeLa cells presented improved accumulation for CHL and CHL-T compared to HY. The phototoxicity presented by the CHL-T was about ten times higher than by CHL, as demonstrated by the MIT assay. CHL-T showed more cytotoxicity to tumoral cell, comparing to non-tumoral cell in short incubation time. The cell death rises proportionally with increasing PSs concentrations, mainly by necrosis. These findings suggest that CHL-T is a potential new photosensitizer for PDT. (C) 2016 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 15/21110-4 - Exploiting Photocatalyzed Reactions Under Continuous Flow Conditions by using Porphyrinoid Systems: (C-FlowPhotoChem)
• Grantee: Kleber Thiago de Oliveira
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/07276-1 - CEPOF - Optics and Photonic Research Center
• Grantee: Vanderlei Salvador Bagnato
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC