Quantum chemistry studies of meta-tetra(hydroxyphenyl)chlorin (mTHPC) and its isomers

Quantum chemistry methods were used to study the meta-tetra(hydroxyphenyl)chlorin (mTHPC) and its isomers. The mTHPC (Foscan®) is a commercial chlorin, used in photodynamic therapy (PDT) and is classified as a second-generation drug in PDT. The present work is to obtain quantum chemistry properties which can explain the high efficiency of the mTHPC compared with its isomers (ortho and para) and other chlorins. Based in the chemical hardness and ionization potential obtained from HOMO and LUMO orbitals energy, our results show that all chlorins have similar reactivity. Moreover, all chlorins have approximately the same capacity to storage energy in the triplet excited state, with energy differences between the ground state and the triplet excited state of 1.38, 1.39 and 1.36 eV for oTHPC, mTHPC and pTHPC, respectively. The calculated UV spectra (a very important quantity which can be correlated with the photosensitizer (PS) efficiency property), shows that the present chlorins all have a peak at 622 nm. Finally, after analysis of the dipole moment differences, between the three isomers, an explanation about the greater mTHPC efficiency in PDT, was possible. Due to its greater lipophilic character, mTHPC is absorbed by tumor cells to a greater degree than oTHPC and pTHPC. Our findings are consistent with literature and can be used to help new drug design for use in PDT.