Porphyrin, Chlorin, and Bacteriochlorin Isothiocyanates: Useful Reagents for the Synthesis of Photoactive Bioconjugates

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Abstract
A novel method for conjugating porphyrins and related molecules to proteins has been developed. The method, which involves synthesizing porphyrins, chlorins, and bacteriochlorins bearing a single amine-reactive isothiocyanate group represents a facile system for protein labeling with these photoactive species. Problems associated with the noncovalent binding of porphyrins to proteins are highlighted, and a method for purifying conjugates to yield exclusively covalently bound porphyrin protein species is demonstrated. Biological activity of porphyrin−bovine serum albumin conjugates formed and purified by these methods is demonstrated using laser scanning confocal microscopy.