Physical chemistry of porphyrins and their interactions with membranes: the importance of pH.

The physicochemical properties of dicarboxylic porphyrins are examined with particular emphasis on acid-base equilibria. Interactions with membranes appear to be dominated by the charge of the propionic acid chains and the hydrophobic character of other peripheral substituents. A physicochemical basis for the effect of pH on the incorporation of porphyrins within membranes is given. The effect of lowered tumour pH on the incorporation of porphyrins within membranes and on porphyrin retention is discussed.