Syntheses and photodynamic properties of glucopyranoside-conjugated indium(III) porphyrins as a bifunctional agent

Abstract

The glucopyranoside-conjugated porphyrins, H 2 TPP {p- O -( CH 2)2- O - OAcGlc } (1), [ InTPP {p- O -( CH 2)2- O - OAcGlc }] NO 3 (2), H 2 TPP {p- O -( CH 2)2- O - Glc } (3), [ InTPP {p- O -( CH 2)2- O - Glc ]- NO 3 (4) and ZnTPP {p- O -( CH 2)2- O - OAcGlc } (5) were synthesized, and characterized by 1 H NMR, 13 C NMR, ESI-MS, UV-vis spectroscopies and elemental analyses. In the 1 H NMR spectrum of 2, two sets of signals were observed for H -atoms of the phenyl group of porphyrin, indicating that 2 has the axial chirality due to a NO 3 ion coordinating to the indium atom. Abilities of the singlet oxygen production of these porphyrins, investigated by using 1,3-diphenylisobenzofuran (DPBF) as a quencher, were higher than those of the free-based and zinc porphyrins, reflecting the heavy atom effect. The photodynamic properties of these porphyrin derivatives were investigated against COLO 679. All of the glucopyranoside-conjugated porphyrins exhibited the high photocytotoxicity compared with Laserphyrin®. Above all, 4 exhibited the highest photocytotoxicity, coinciding with the high abilities of this complex for the singlet oxygen production and the cell permeability.