Chlorophyllin Derivatives as Photosensitizers: Synthesis and Photodynamic Properties

Author(s)

Uchoa, Adjaci F. ^{[1, 2]} ; Konopko, Aaron M. ^[1] ; Baptista, Mauricio S. ^[1]

Affiliation

^[1] Univ Sao Paulo, Dept Bioquim, BR-05513970 Sao Paulo, SP - Brazil

^[2] Univ Camilo Castelo Branco, Inst Engn Biomed, BR-12247016 Sao Jose Dos Campos, SP - Brazil

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 26, n. 12, p. 2615-2622, DEC 2015.
• Web of Science Citations: 2

Abstract

Two new photosensitizers (PSs) derived from copper-chlorophyllin were designed to have excitation wavelengths appropriate for the use in photodynamic therapy (PDT) and to have amphiphilic character with positive charge, which favors binding to cell membranes and walls and the intracellular localization in mitochondria. Herein we describe the synthesis and characterization of several properties of these two new PS, i.e., photophysical (absorption, fluorescence and singlet oxygen emission quantum yields, Φf and ΦΔ, respectively), physical-chemical (aggregation) and photobiological (binding, incorporation and cell killing). As expected, the aggregation affected not only the absorption spectra but also lowered considerably the values of Φf and ΦΔ, which could be controlled by the interaction of the PS with aqueous micelles. In vitro studies were performed in cells, mitochondria, and vesicles to determine uptake, membrane binding, cytotoxicity, phototoxicity, and intracellular localization. The positively charged derivatives showed to be considerably more efficient for cell killing than methylene blue. (AU)

• FAPESP's process: 13/07937-8 - Redoxome - Redox Processes in Biomedicine
• Grantee: Ohara Augusto
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• FAPESP's process: 12/50680-5 - Photosensitization in life sciences
• Grantee: Mauricio da Silva Baptista
• Support Opportunities: Research Projects - Thematic Grants