Riboflavin derivatives for enhanced photodynamic activity against Leishmania parasites

Author(s)

Silva, Alexandre Vieira ^{[1, 2]} ; Lopez-Sanchez, Almudena ^[3] ; Junqueira, Helena Couto ^[1] ; Rivas, Luis ^[3] ; Baptista, Mauricio S. ^[1] ; Orellana, Guillermo ^[2]

Affiliation

^[1] Univ Sao Paulo, Inst Chem, Sao Paulo - Brazil

^[2] Univ Complutense Madrid, Dept Organ Chem, E-28040 Madrid - Spain

^[3] CSIC, Ctr Invest Biol, Dept Physicochem Biol, Madrid 28040 - Spain

• Document type: Journal article
• Source: Tetrahedron; v. 71, n. 3, p. 457-462, JAN 21 2015.
• Web of Science Citations: 6

Abstract

Riboflavin derivatives with various substituents (O-acyl, N-methyl, N-alkylcarboxyalkyl or N-alkyl(trialkyl) ammonium) have been prepared and spectroscopically characterized (absorption, emission and fluorescence quantum yields). Their quantum yields of photosensitized singlet molecular oxygen production (Phi(Delta) 0.24-0.58) and octanol/water partition coefficients (P-ow <= 0.01-11) were measured. Preliminary studies indicate that all derivatives display higher phototoxicity against the human protozoan parasite Leishmania than the parent riboflavin, with negligible toxicity in the absence of light. Their photodynamic action shows a higher correlation with Pow than with Phi(Delta), opening up their potential application to cutaneous diseases treatment. (C) 2014 Elsevier Ltd. All rights reserved. (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