Meso-tetraphenyl porphyrin derivatives: The effect of structural modifications on binding to DMPC liposomes and albumin

Investigating the possible use of a tetra (hydroxyphenyl) porphyrin as a fluorescence probe for the supramolecular detection of phospholipids

“…Even if the latter is the most probable explanation, both hypotheses confirmed a location of m-THPP close to that of DPH in the interior of phospholipid bilayer, in agreement with our recent study in DPMC liposomes [11].…”

“…In a recent work [11], we demonstrated that some tetraphenyl porphyrin (TPP) derivatives exhibit an important enhancement of their fluorescence emission in the presence of dimyristoylphosphatidylcholine (DMPC) liposomes. The emission enhancement is due to the fact that the porphyrin is almost not fluorescent in aqueous media due to the self-aggregation process, but associated to lipids a progressive regeneration of the fluorescent monomer occurs inducing a very important increase in fluorescence emission.…”

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

“…The extent of penetration into the phospholipid bilayer of DMPC was dependent on the number of phenyl groups present and the distance of the glycosyl unit from the macrocyle. The dendrimeric structures showed the deepest penetration while the presence of diethylene glycol spacer increased the insertion of macrocycle compared to those without the linker [382] . The incorporation of glycosyl units into a hemoprotein is quiet rare.…”

“…Porphyrin 269 and DMPC mixed liposomes aggregated on addition of α-mannose specific concanavalin A suggesting that the macrocycle was embedded into the phospholipid bilayer while the sugar unit extended out into the aqueous phase [204] . A range of hydroxylated (mTHPP, pTHPP, 473, 512b) and glycosylated (30, 39, 206, 504b) derivatives of TPP were also examined for the effect their different structural characteristics had on their binding affinity to DMPC liposomes and HSA [382] . The glycosyl derivatives displayed greater solubility in aqueous medium but such conjugation decreased the affinity for the phospholipid bilayer of DMPC in all cases but increased binding to HSA with 39 displaying the best results.…”

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

“…Thus, the carbohydrate porphyrins and chlorins exhibit an intricate interplay of substituent pattern, regiochemistry and linker dependence and require quite detailed QSAR analyses. The porphyrins used in these studies were subsequently used for binding studies with DMPC liposomes and albumin [71]. Only limited aggregation in polar media and rapid binding to DMPC liposomes was found for the more polar compounds.…”