TY - JOUR

T1 - A quantitative structure-property relationship (QSPR) study of singlet oxygen generation by pteridines

AU - Buglak, Andrey A.

AU - Telegina, Taisiya A.

AU - Kritsky, Mikhail S.

PY - 2016

Y1 - 2016

N2 - The QSPR method is used in photochemistry for the prediction of the absorption wavelength, fluorescence intensity, photolysis quantum yield, etc. However, to our knowledge, no attempts have been made to use the quantum yield of singlet oxygen (O-1(2)) generation (Phi(Delta)) as an analyzed parameter in a QSPR study. We performed QSPR analysis of 29 pteridine compounds (including pterin and flavin sensitizers) for their ability to produce singlet oxygen in aqueous (D2O) solutions. Pteridines are ubiquitously present in living systems (mostly as coenzymes), possess high photochemical activity and have multiple applications as photosensitizers. Our goal was to develop a QSPR model for the fast virtual screening and prediction of the O-1(2) generation quantum yield of pteridines. Quantum-chemical descriptors were calculated using the AM1 semi-empirical method. The ability of pteridines to generate singlet oxygen was found to be significantly correlated with the HOMO orbital energy (R-2 = 0.806) and electronegativity (R-2 = 0.840). The best QSPR model obtained using electronegativity, dipole density and electrostatic charge of the N3 atom of the pteridine system allows us to predict Phi(Delta) of pterin and flavin photosensitizers. The model possesses high internal stability (q(2) = 0.881), as well as high predicting ability for the external dataset (pred_R-2 = 0.873). More QSPR analysis is needed for the prediction of Phi(Delta) of pteridines and other groups of sensitizers in aqueous as well as in non-polar solutions.

AB - The QSPR method is used in photochemistry for the prediction of the absorption wavelength, fluorescence intensity, photolysis quantum yield, etc. However, to our knowledge, no attempts have been made to use the quantum yield of singlet oxygen (O-1(2)) generation (Phi(Delta)) as an analyzed parameter in a QSPR study. We performed QSPR analysis of 29 pteridine compounds (including pterin and flavin sensitizers) for their ability to produce singlet oxygen in aqueous (D2O) solutions. Pteridines are ubiquitously present in living systems (mostly as coenzymes), possess high photochemical activity and have multiple applications as photosensitizers. Our goal was to develop a QSPR model for the fast virtual screening and prediction of the O-1(2) generation quantum yield of pteridines. Quantum-chemical descriptors were calculated using the AM1 semi-empirical method. The ability of pteridines to generate singlet oxygen was found to be significantly correlated with the HOMO orbital energy (R-2 = 0.806) and electronegativity (R-2 = 0.840). The best QSPR model obtained using electronegativity, dipole density and electrostatic charge of the N3 atom of the pteridine system allows us to predict Phi(Delta) of pterin and flavin photosensitizers. The model possesses high internal stability (q(2) = 0.881), as well as high predicting ability for the external dataset (pred_R-2 = 0.873). More QSPR analysis is needed for the prediction of Phi(Delta) of pteridines and other groups of sensitizers in aqueous as well as in non-polar solutions.

KW - PYROPHEOPHORBIDE DERIVATIVES

KW - PHOTOPHYSICAL PROPERTIES

KW - PHOTODYNAMIC THERAPY

KW - PTERIN DERIVATIVES

KW - CONGENERIC SERIES

KW - CHARGE-TRANSFER

KW - TRIPLET-STATE

KW - PREDICTION

KW - PHOTOSENSITIZERS

KW - PHOSPHORESCENCE

U2 - 10.1039/c6pp00084c

DO - 10.1039/c6pp00084c

M3 - статья

VL - 15

SP - 801

EP - 811

JO - Photochemical and Photobiological Sciences

JF - Photochemical and Photobiological Sciences

SN - 1474-905X

IS - 6

ER -