Quantitative structure property relationships to evaluate the photosensitizing capability in porphyrins and chlorins

Abstract

ABSTRACT:The wavelength of the Q band (k Q ) of sixteen compounds (porphyrins and chlorins) was related to eight descriptors (aromatic, electrostatic, and reactivity ones) by using quantitative structure property relationships (QSPR). These descriptors were calculated using density functional theory (DFT). No single linear regressions were found. So, our work demonstrates that k Q does not depend on a unique property; rather it is a multidimensional parameter. From twelve QSPR models obtained, four of them yielded regression coefficients over 0.8. In addition, the k Q values resulting from our QSPR models are closer to experiment than time dependent-DFT calculated ones. It has been proved the power of QSPR models to reproduce and predict the k Q values for new porphyrin derivatives with potential capability to be used in Photodynamic Therapy.

mTHPC – A drug on its way from second to third generation photosensitizer?

“…In parallel, advances in porphyrin chemistry have made the construction of bioconjugates much easier and now allow the preparation of selected regioisomers and more unsymmetrical derivatives. Computational approaches for the prediction of suitable candidate molecules are still in its infancy and might never reach practical use [94]. However, the picture evolving for mTHPC analogs has reached a point where comparative QSAR studies are possible and able to identify suitable compounds for use in more advanced bioconjugate targeting systems.…”

Quantum chemical studies of porphyrin‐ and expanded porphyrin‐based systems and their potential applications in nanoscience. Latin America research review

“…The same set of porphyrins and chlorins was used to explore the relation between the wavelength of the Q band (λ Q ) (the longest wavelength absorption) and eight descriptors (aromatic, electrostatic, and reactivity ones) by using quantitative structure property relationships (QSPR). [75] These descriptors were calculated using DFT. It was found that λ Q does not depend on a unique property; it is rather a multidimensional parameter.…”

A molecular study of tetrakis(p -methoxyphenyl)porphyrin and its Zn(II) complex as discotic liquid crystals

“…Macrocycles constituted by pyrrolic rings, such as metal free porphyrins, porphyrazines, phthalocyanines, and their respective metal complexes are involved in many chemical processes, such as molecular catalysis, electron transfer, photosynthesis, and light harvesting in devices such as dye sensitized solar cells . Synthesis and many applications of these systems have been carried out by several different research groups in order to develop new functional materials.…”