In Vitro and In Vivo Photocytotoxicity of Boron Dipyrromethene Derivatives for Photodynamic Therapy

Abstract

To understand the effects of substitution patterns on photosensitizing the ability of boron dipyrromethene (BODIPY), two structural variations that either investigate the effectiveness of various iodinated derivatives to maximize the "heavy atom effect" or focus on the effect of extended conjugation at the 4-pyrrolic position to red-shift their activation wavelengths were investigated. Compounds with conjugation at the 4-pyrrolic position were less photocytotoxic than the parent unconjugated compound, while those with an iodinated BODIPY core presented better photocytotoxicity than compounds with iodoaryl groups at the meso-positions. The potency of the derivatives generally correlated well with their singlet oxygen generation level. Further studies of compound 5 on HSC-2 cells showed almost exclusive localization to mitochondria, induction of G(2)/M-phase cell cycle block, and onset of apoptosis. Compound 5 also extensively occluded the vasculature of the chick chorioallantoic membrane. Iodinated BODIPY structures such as compound 5 may have potential as new photodynamic therapy agents for cancer.

Bipolar tetraether lipids derived from thermoacidophilic archaeon Sulfolobus acidocaldarius for membrane stabilization of chlorin e6 based liposomes for photodynamic therapy

“…For each liposomal preparation, the experiment was performed at least three times. Acquisition of images was made pre-and post-photodynamic therapy and was compared and graded according to the criteria described elsewhere with minor modification [3,34]. Briefly, depending on the degree of the vascular occlusion of CAM after PDT, the response was graded according to the degree of vascular closure and/or destruction representing the level of treatment (Table 2).…”

Angiostatic kinase inhibitors to sustain photodynamic angio-occlusion

“…The CAM model is often used as a model for PDT-induced angioocclusion [23,34]. We observed that Visudyne ® -PDT, applied at EDD11, induced an efficient closure of the vasculature ( Fig.…”

Syntheses and photodynamic activity of some glucose-conjugated BODIPY dyes

“…Moreover, the BODIPY PSs with heavy atoms, such as I, Br, Se, S etc. may offer increased dark toxicity, and altered biodistribution as well as pharmacokinetics [39,40].…”