Quantitative structure-activity relationship analysis of perfluoroiso-propyldinitrobenzene derivatives known as photosystem II electron transfer inhibitors.
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.
Department of Chemistry, Gazi University, Ankara, Turkey. mkaracan@gazi.edu.tr
Mehmet Sayım
MS
Karacan
Ciğdem
C
Yakan
Mehmet
M
Yakan
Nurcan
N
Karacan
Sergey K
SK
Zharmukhamedov
Alexandr
A
Shitov
Dmitry A
DA
Los
Vyacheslav V
VV
Klimov
Suleyman I
SI
Allakhverdiev
D004136:Dinitrobenzenes / Q000737:chemistry / Q000494:pharmacology*; D004579:Electron Transport / Q000187:drug effects; D045332:Photosystem II Protein Complex / Q000037:antagonists & inhibitors*; D021281:Quantitative Structure-Activity Relationship
D004136:Dinitrobenzenes; D045332:Photosystem II Protein Complex