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Quantitative structure–activity relationship analysis of perfluoroiso-propyldinitrobenzene derivatives known as photosystem II electron transfer inhibitors

2012; Elsevier BV; Volume: 1817; Issue: 8 Linguagem: Inglês

10.1016/j.bbabio.2012.01.010

1879-2650

Mehmet Sayım Karacan, Çiğdem Yakan, Mehmet Yakan, Nurcan Karacan, Sergey K. Zharmukhamedov, Alexandr V. Shitov, Dmitry A. Los, Vyacheslav V. Klimov, Suleyman I. Allakhverdiev,

Antioxidant Activity and Oxidative Stress

Quantitative structure-activity relationship (QSAR) analysis of the twenty-six perfluoroisopropyl-dinitrobenzene (PFIPDNB) derivatives was performed to explain their ability to suppress photochemical activity of the plants photosystem II using chloroplasts and subchloroplast thylakoid membranes enriched in photosystem II, called DT-20. Compounds were optimized by semi-empirical PM3 and DFT/B3LYP/6-31G methods. The Heuristic and the Best Multi-Linear Regression (BMLR) method in CODESSA were used to select the most appropriate molecular descriptors and to develop a linear QSAR model between experimental pI(50) values and the most significant set of the descriptors. The obtained models were validated by cross-validation (R(2)(cv)) and internal validation to confirm the stability and good predictive ability. The obtained eight models with five-parameter show that: (a) coefficient (R(2)) value of the chloroplast samples are slightly higher than that of the DT-20 samples both of Heuristic and BMLR models; (b) the coefficients of the BMLR models are slightly higher than that of Heuristic models both of chloroplasts and DT-20 samples; (c) The YZ shadow parameter and the indicator parameter, for presence of NO(2) substituent in the ring, are the most important descriptor at PM3-based and DFT-based QSAR models, respectively. This article is part of a Special Issue entitled: Photosynthesis Research for Sustainability: from Natural to Artificial.