In vitro phototoxicity of glycoconjugated porphyrins and chlorins in colorectal adenocarcinoma (HT29) and retinoblastoma (Y79) cell lines

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

“…The para-O-β-glucose porphyrin derivative 68 was found to have the best phototoxicity compared to the parent porphyrin system with an IC 50 of 0.9 μM and no cytotoxicity in the absence of light with an IC 50 >15 μM. However, this compound is less PDT active compared to the Deg-porphyrin conjugates described previously (63)(64)(65). The extension of the linker between the glycoconjugate and the chromophore appears to significantly increase the PDT activity.…”

“…Expanding on earlier work using 57, 58 and 65 in HT29 and Y79 cell lines, a number of porphyrin and chlorin derivatives were explored for photocytotoxicity using weaker light doses of 1.8 J.cm -2 and excitation at >540 nm after 24 h incubation. 63 Even though the glycoconjugated derivatives had lower PDT activity compared to mTHPC they displayed IC 50 values of 2.4-0.05 μM against Y79 cells. The para-O-β-glucose porphyrin derivative 68 was found to have the best phototoxicity compared to the parent porphyrin system with an IC 50 of 0.9 μM and no cytotoxicity in the absence of light with an IC 50 >15 μM.…”

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

“…Also highlighted was the difference in the anomeric configuration the p-O-Deg-O-α-Gal compound (205, IC 50 = 0.05 μM) [198] which shows a 10-fold greater phototoxicity than the β-glucose conjugate (308, IC 50 = 0.6 μM) in Y79 cells as well as mTHPC IC 50 = 0.6 μM. Here, porphyrins 205 and 114 were identified as good PDT PS [210] . Similarly, the photochemical properties and the in vitro photocytotoxicity in HeLa cells of the four chlorin derivatives 514d-g were investigated [262] .…”

“…The glycoconjugated derivatives had lower PDT activity compared to mTHPC as well as their respective parent compounds, displaying IC 50 = 2.4-0.05 μM against Y79 cells. Among all the derivatives studied the tris-p-O-β-glucose porphyrin derivative 114 was found to have the best phototoxicity versus cytotoxicity activity compared to the parent porphyrin system with an IC 50 = 0.9 μM [210] . However, this compound is less PDT active compared to the diethyleneglycol porphyrin conjugates described before (204)(205)(206) [198] including the glucose derivative 308.…”

mTHPC – A drug on its way from second to third generation photosensitizer?

“…As before the unsymmetrical derivatives with three glucose residues showed the highest phototoxicity and no cytotoxicity. The need for real QSAR studies was indicated by the fact that linker groups between the meso phenyl and sugar residue (here diethyleneglycol spacers) and the anomeric configuration significantly improved the IC 50 values by about one order of magnitude [70]. Overall, compounds derived from the 5,10,15-tri(hydroxyphenyl)-20-phenyl frameworks (19 and 20) gave the best results.…”