Tritolylporphyrin dimer as a new potent hydrophobic sensitizer for photodynamic therapy of melanoma.

Abstract

We report the synthesis, photochemical and photophysical properties and preliminary studies on biological effect of a new tritolylporphyrin dimer (T-D). Absorption and emission properties of T-D suggest its possible use in photodynamic therapy. T-D is capable of singlet oxygen production with 0.8 quantum yield. It also has a high photostability. The photodynamic properties of the dimer were examined following the growth of SKMEL 188 (human melanoma) cells irradiated with red light (cut off < 630 nm). The surviving fraction of the cells decreased about 3-fold (vs. non-irradiated cells) for an 81 J/cm dose. Our results suggest that tritolylporphyrine dimer T-D may be an interesting hydrophobic sensitizer for photodynamic therapy.

Photodynamic effects of two water soluble porphyrins evaluated on human malignant melanoma cells in vitro.

“…Due to these limitations chemists were challenged to replace Photofrin with other porphyrins or new agents with bioactivity suitable for use in PDT. Currently, various second-generation photosensitisers, such as chlorins, phtalocyanins and others are under investigation (Wesley et al, 2000;Drzewiecka et al, 2001;Lottner et al, 2002).…”

The Menace of Melanoma: A Photodynamic Approach to Adjunctive Cancer Therapy

“…Zealand albino rabbit eyes liposomal preparation of benzoporphyrin derivative (BPD), verteporfin [136] in vitro S91 mouse and SKMEL 188 human melanoma cells indocyanine green (ICG) [137] in vitro B16A45 (B16) mouse melanoma cells delta-aminolevulinic acid (ALA) and meta(tetrahydroxyphenyl)chlorin or m-THPC [138] in vitro B16 mouse melanoma cells m-THPC and four apoptosis inhibitors: BAPTA-AM, Forskolin, DSF, and Z.VAD.fmk [47] in vitro Bro, SKMel-23, SKMel-28 5-aminolevulinic acid (ALA) [139] In vitro SKMEL 188 human melanoma cells tritolylporphyrin dimer (T-D). [140] in vivo [155] in vivo 10 choroidal melanomas in rabbits liposomal preparation of benzoporphyrin derivative [156] in vivo M2R mouse melanoma tumors implanted in CD1 nude mice bacteriochlorophyll-serine (Bchl-Ser), [157] in vitro uveal melanoma cells hematoporphyrin esters (HPE) [158] in vivo For melanoma treatment, where PDT will be more effective as a post-operative adjunctive treatment, very few reports highlight its effectiveness even though laboratory studies using melanoma cells show promise. Clinically, PDT has shown promise in the treatment of both ocular amelanotic melanomas [164] and skin metastases [165] however, more extensive clinical studies need to be conducted before PDT is accepted as the adjunctive therapy of choice [166] ( Table 3).…”

An analysis of the photophysical and optical limiting properties of a novel 1,3,5-tristyrylBODIPY dye

“…Photosensitization by molecular dyes forms the basis of singlet oxygen generation for applications such as photodynamic therapy (PDT) [1], photodynamic antimicrobial chemotherapy (PACT) [2,3], and the photodegradation of organic pollutants [4]. Molecular photosensitizers such as phthalocyanines, naphthalo cyanines, porphyrins, chlorins, bacteriochlorins, and texa phyrins [5][6][7][8] are among the most widely used dyes in PDT research. Structurallymodified boron dipyrromethene (BODIPY) dyes [9][10][11][12] can also be used in this context.…”