Journal
ELECTROCHIMICA ACTA
Volume 120, Issue -, Pages 334-343Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.electacta.2013.12.053
Keywords
Photosynthetic inhibitors; Redox properties; Rubrolides; Butyrolactones
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Funding
- CNPq (Conselho Nacional de Desenvolvimento Cientifico e Tecnologico)
- FAPEMIG (Fundacao de Amparo Pesquisa do Estado de Minas Gerais)
- FAPERJ (Fundacao Carlos Chagas Filho de Amparo Pesquisa do Estado do Rio de Janeiro)
- University of Ferrara (Fondo di Ateneo per la Ricerca)
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To understand and predict the relationship between the redox potential and the inhibitory effect of rubrolide analogues upon the photosynthetic electron transport chain, their redox properties were studied. The reduction potential was determined experimentally in DMSO by means of cyclic voltammetry, and theoretically by using B3LYP/6-31 G(d,p) and MPWB1 K/TZVP computational methods. A good correlation was obtained between the two datasets, MPWB1 K/TZVP being the best methodology (correlation coefficient of 0.965 and standard deviation of 0.034, against 0.932 and 0.047 for B3LYP/6-31G(d,p)). A significant relationship was observed between the redox potential of the rubrolide analogues and their ability to interfere with the Hill reaction: the higher the first reduction potential, the more effective the inhibitor. These results will allow for predicting the behavior of novel analogues as inhibitors of the Hill reaction, and directing the synthetic strategy towards more potent inhibitors targeting the photosynthetic electron transport. (C) 2013 Elsevier Ltd. All rights reserved.
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