Tetrapyrrolic Glycosylated Macrocycles for an Application in PDT

Abstract

The synthesis and characterization of amphiphilic glycoconjugated porphyrins, benzochlorin, and azaporphyrins were reported. Among these molecules, several were found to be efficient photosensitizers in an in vitro assay using the human tumoral cell line HT29. Moreover, glycosylated benzochlorin and azaporphyrins, whose absorption bands in the red region of the visible spectrum are substantially increased as compared to porphyrins, display a good photocytotoxicity on tumor cells after irradiation with wavelength above 590 nm. © 1999 Society of Photo-Optical Instrumentation Engineers.

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

“…In comparison the parent, unconjugated derivative 551b exhibited no phototoxicity [277] . HT29 is also susceptible to a range of other amphiphilic porphyrins, benzochlorins and azaporphyrins; again glycosylated benzochlorin and azaporphyrins displayed the best photocytotoxcity when irradiated at 590 nm [356] . In another study on OEP-type benzochlorins, all PSs (553-556b, 557) were found to be active in vitro on radiation-induced fibrosarcoma (RIF) tumor cells.…”

Current Developments in Using MESO-(TETRA) Substituted Porphyrins for PDT

“…Laranjo et al aimed to exploit this heavy atom effect by functionalizing hydroxylporphyrin derivatives with bromine via formation of 5,10,15,20-tetrakis(2-bromo-3-hydroxyphenyl)porphyrin 9 and 5,15-bis(2-bromo-3-hydroxyphenyl)porphyrin 10 as represented in Figure 4. 26 In vitro studies with A375 and WiDr cells showed that for colorectal adenocarcinoma cells, IC 50 values of 464 nM for 9 and 180 nM for 10 could be determined. Melanoma cells, with an IC 50 of 100 nM for 10 and 50 nM for 9, were more susceptible to both sensitizers.…”

“…50 For example, they synthesized glucosyl conjugated triand tetra(metahydroxyphenyl)chlorins and investigated their PDT effect in HT29 human colorectal adenocarcinoma cells (Fig. 12).…”

Structure-Photodynamic Effect Relationships of 24 Glycoconjugated Photosensitizers in HeLa Cells

“…17,27) The extensive variation of reported glycoconjugated photosensitizers and different types of photocytotoxicity tests employed make rather a difficulty to obtain the keys for rational design of glycoconjugated photosensitizers. We previously reported the synthesis of a library of 16 glycoconjugated porphyrin derivatives 28) and 8 glycoconjugated chlorins 29) (Chart 1).…”

“…Since the discovery of the glycoconjugated porphyrin derivatives by Fülling et al, 7) many glycoconjugates have been reported. [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][27][28][29][30][31][32]34) Momenteau and Mailard et al synthesized a number of O-glycosylated tetraphenylporphyrins (TPPs) and chlorins (TPCs) having various substituents (phenyl, alkyl and so on) and examined 1 O 2 generation, partition coefficients and photocytotoxicity in KB cells. 17) They reported that the photocytotoxicity varies with the sugar unit attached, and concluded that planar structure and amphiphilic character were the keys to a potent photocytotoxic effect on KB cells.…”