Quantum-chemistry descriptors for photosensitizers based on macrocycles

Author(s)

Bettanin, Fernanda ; Antonio, Felipe C. T. ; Honorio, Kathia M. ; Homem-de-Mello, Paula

• Document type: Journal article
• Source: CHEMICAL BIOLOGY & DRUG DESIGN; v. 89, n. 2, p. 207-220, FEB 2017.
• Web of Science Citations: 4

Abstract

Phthalocyanines, porphyrins, and chlorins have been widely studied as photosensitizers. Both experimental and computational strategies are employed in order to propose new and more active molecules derived from those macrocycles. In this context, there are two main strategies used: (i) the addition of different substituents and (ii) the complexation of the macrocycle with different metallic ions. In this work, we present selected descriptors based on quantum chemistry calculations for forty macrocycles, including some approved drugs. We have found that density functional theory is a suitable methodology to study the large sets of molecules when applying the B3LYP/LanL2DZ methodology for geometry optimization and TD-OLYP/6-31G(d) for absorption spectrum. The inclusion of solvent effects by means of continuum model is important in order to obtain the accurate electronic data. We have verified that by bonding charged or polar substituents to the macrocycle, it is possible to enhance water solvation as well as to improve spectroscopic properties because molecular orbital contributions for Q band can be affected by some substituents. Selected descriptors, electronic and steric, were pointed out as important to propose the new photosensitizers. (AU)

• FAPESP's process: 12/50680-5 - Photosensitization in life sciences
• Grantee: Mauricio da Silva Baptista
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 10/19790-3 - Theoretical study of porphyrins, phthalocyanines and CHLORINES with enphasis for use in photodynamic therapy
• Grantee: Fernanda Bettanin
• Support Opportunities: Scholarships in Brazil - Doctorate