caa a22 4500 463208609 CHVBK 20180405153133.0 cr unu---uuuuu 170326e20070401xx s 000 0 eng 10.1007/s10863-007-9075-0 doi (NATIONALLICENCE)springer-10.1007/s10863-007-9075-0 Interaction of cationic meso -porphyrins with liposomes, mitochondria and erythrocytes [Elektronische Daten] [Fabio Engelmann, Ildemar Mayer, Dino Gabrielli, Henrique Toma, Alicia Kowaltowski, Koiti Araki, Mauricio Baptista] Two series of cationic porphyrins meso-(3N-methylpyridinium)phenylporphyrin (3P1, 3P2c, 3P2t, 3P3 and 3P4) and meso-(4N-methylpyridinium)phenylporphyrin (4P1, 4P2c, 4P2t, 4P3 and 4P4) were studied to obtain a comprehensive understanding of factors that influence the binding of cationic porphyrins to liposomes and mitochondria, as well as their photodynamic efficiencies in erythrocytes. Binding and photodynamic efficiency were found to be inversely proportional to the number of positively charged groups and directly proportional to n-octanol/water partition coefficients (log POW), except for the cis molecules 3P2c and 4P2c. In the cis molecules, binding and photodynamic efficiency were much higher than expected, indicating that specific interactions not accounted by log POW enhance photodynamic efficiency. The effect of mitochondrial transmembrane electrochemical potentials on cationic porphyrin binding constants was estimated to be as large as 15%, and may be useful to selectively target this organelle when promoting photodynamic therapy to induce apoptosis. Springer Science+Business Media, LLC, 2007 Cationic porphyrins nationallicence Amphiphilic porphyrins nationallicence Membrane binding nationallicence Partition coefficient nationallicence Erythrocyte lysis nationallicence Photodynamic activity nationallicence Engelmann Fabio Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut Mayer Ildemar Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut Gabrielli Dino Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut Toma Henrique Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut Kowaltowski Alicia Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut Araki Koiti Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut Baptista Mauricio Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut Journal of Bioenergetics and Biomembranes Kluwer Academic Publishers-Plenum Publishers; http://www.springer-ny.com 39/2(2007-04-01), 175-185 0145-479X 39:2<175 2007 39 10863 https://doi.org/10.1007/s10863-007-9075-0 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10863-007-9075-0 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Engelmann Fabio Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut NATIONALLICENCE 700 1- Mayer Ildemar Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut NATIONALLICENCE 700 1- Gabrielli Dino Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut NATIONALLICENCE 700 1- Toma Henrique Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut NATIONALLICENCE 700 1- Kowaltowski Alicia Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut NATIONALLICENCE 700 1- Araki Koiti Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut NATIONALLICENCE 700 1- Baptista Mauricio Instituto de Química, Universidade de São Paulo, C. Postal 26077, CEP 05513-970, São Paulo, Brazil aut NATIONALLICENCE 773 0- Journal of Bioenergetics and Biomembranes Kluwer Academic Publishers-Plenum Publishers; http://www.springer-ny.com 39/2(2007-04-01), 175-185 0145-479X 39:2<175 2007 39 10863 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer