5,20-BIS(4-Sulphophenyl)-10,15-Bis(2-Methoxy-4-Sulphophenyl)-21-Thiaporphyrin as a new Potent Sensitizer in Photodynamic Therapy

Abstract

The main purpose of the study was to investigate the effectiveness of a new photosensitizer for photodynamic therapy. 5,20-bis(4-sulphophenyl)-10,15-bis (2-methoxy-4-sulphophenyl)-21-thiaporphyrin (21-thiaporphyrin) was compared to chlorin e6 and tetra(m-hydroxyphenyl)porphyrin (m-THPP) for its ability to sensitize tumors and skin to light. Chlorin e6 and m-THPP induced a strong tumor and skin photosensitization. In contrast, the same doses of 21-thiaporphyrin produced no skin sensitization and gave approximately 10 mm tumor necrosis after light exposure, in comparison to the 5-6 mm necrosis induced by chlorin e6 or m-THPP under identical conditions. 21-Thiaporphyrin, tested as a potential photosensitizer, induced no skin sensitization even at doses as high as 7.5 mg/kg body weight. 21-Thiaporphyrin presents a high potency in tumor sensitizing, i.e. a feature required for an efficient photosensitizer in photodynamic therapy applications.

New potent sensitizers for photodynamic therapy: 21-oxaporphyrin, 21-thiaporphyrin and 21,23-dithiaporphyrin induce extensive tumor necrosis

“…Previous studies revealed that STSP exerts its photodynamic action both in vitro on human cancer cell lines, i.e. LS 180 and CX-2 colon adenocarcinomas, and Hu 1703 He urinary bladder transitional cell carcinoma (Marcinkowska et al 1997) and in vivo on Morris hepatoma growing in Bualo rats (Zio økowski et al 1995).…”

“…The electronic spectra of new sensitizers revealed that the most red-shifted Q band is located at 670±695 nm, and this is a favorable spectroscopic feature for PDT. Previous experiments on animal tumor models revealed that 21-thiaporphyrin, (Marcinkowska et al 1997;Zio økowski et al 1995), is a potent tumor photosensitizer. Now, we report on other compounds that can be used in photodynamic therapy, namely 21-oxaporphyrin (OXA) and 21,23-dithiaporphyrin (DTP).…”

Recent developments in heteroporphyrins and their analogues

“…The aggregation properties of 212 and 213 were similar to regular anionic water-soluble porphyrins [179]. Latos-Grażyński and co-workers [180,181] have used similar reaction conditions and prepared the disulfonated water-soluble 21-selenaporphyrin in which the sulfonated groups were at oposition (the structure is not shown in Chart 18). Detty and co-workers [182,183] recently synthesized the tetrasulfonated water-soluble 21-thiaporphyrin 212, 21,23dithiaporphyrin 213 and 21,23-diselenaporphyrin 214 as tetrasodium salts by sulfonation of the corresponding porphyrin by treatment with sulfuric acid followed by treatment with NaOH.…”

Temoporfin (Foscan®, 5,10,15,20‐Tetra(m‐hydroxyphenyl)chlorin)—A Second‐generation Photosensitizer†,‡

“…The only significant drawback of these porphyrins was their weak absorption in the area of 630 nm which meant nothing was gained in this regard compared to Photofrin Ò . Nevertheless, a number of in vitro and in vivo tests established the basic PDT properties and advantage of the mTHPP porphyrin (33)(34)(35)(36)(37)(38)(39)(40)(41).…”