New Route to Glycosylated Porphyrins via Aromatic Nucleophilic Substitution (SNAr)—Synthesis and Cellular Uptake Studies

Abstract

Glycoporphyrins are group of compounds of high value for the purpose of photodynamic therapy and other biomedical applications. Despite great progress in the field, new diversity-oriented syntheses of carbohydrate-porphyrin hybrids are increasingly desired. Herein, we present efficient, mild, and metal-free conditions for synthesis of glycoporphyrins. The versatile nature of the SNAr procedure is presented in 16 examples. Preliminary biological studies have been conducted on the cytotoxicity and cellular uptake of the final molecules.

Suzuki‐Miyaura Reaction of Glycals with Base‐Labile Protecting Groups as a New Route to Glycoporphyrins

“…Despite the intensive progress in the area of glycoporphyrinoids syntheses and different approaches, [20–31] there is still need to provide new, original and versatile strategies towards them. It is probably due to the fact that general methodologies are difficult to achieve because of a very distant nature of both subunits.…”

“…And on the other hand the carbohydrate moiety allows to exploit the Warburg effect and therefore intensification of the PS affinity towards cancer cells. [18,19] Despite the intensive progress in the area of glycoporphyrinoids syntheses and different approaches, [20][21][22][23][24][25][26][27][28][29][30][31] there is still need to provide new, original and versatile strategies towards them. It is probably due to the fact that general methodologies are difficult to achieve because of a very distant nature of both subunits.…”

Rod-like nanostructures through amphiphilic OPE-porphyrin self-organization

“…17 Furthermore, since carbohydraterecognized proteins are usually overexpressed on the membrane of certain tumor cells, the introduction of one [18][19][20][21][22][23] up to four sugar moieties on a porphyrin has led to several targeted PDT applications. [24][25][26][27] Another interesting class of chromophores are oligo-phenylene-ethynylenes (OPEs). These systems have been widely exploited as rigid spacers able to electronically couple acceptor and donor supramolecular porphyrinoid based dyads [28][29][30] or to provide optimal separation in selfassembled monolayers 31 or in semiconductor nanoparticles for electronic applications.…”