Spectrophotometric protonation titrations were performed for the trimethyl esters (TME) of chlorin e6 (31,32-didehydrorhodochlorin-15-acetic acid) and the 71-acetal of rhodin g7 (31,32-didehydrorhodochlorin-71-oxo-15-acetic acid) using HCl as the acid and methanol as the solvent. For rhodin g7 TME, the 71-acetal formation could be clearly detected as the first step in the titration. Only two spectroscopically different protonated species were observed for each chlorin derivative in addition to the neutral forms. The two protonated species were assigned to the monocation and dication of each chlorin derivative. The following p K a values were obtained: p K3 = 4.63 and p K4 = 0.62 for chlorin e6 TME and p K3 = 4.40 and p K4 = 0.60 for the acetal of rhodin g7 TME. The protonation titration for chlorin e6 TME with HCl in acetic acid afforded UV-vis spectra similar to those obtained with HCl in methanol. The UV-vis spectrometric parameters are given for the neutral forms of chlorin e6 TME, rhodin g7 TME and its 71-acetal, as well as for the mono- and diprotonated species of chlorin e6 TME and rhodin g7 TME acetal. The protonation titration results of the chlorin e6 derivatives are compared with those previously obtained for phytyl/methyl pyropheophorbide a.
Photodynamic Therapy Mediated by a Novel Chlorin Derivative, TONS 501-Na, in EMT6 cells