Carbohydrate–Porphyrin Conjugates with Two‐Photon Absorption Properties as Potential Photosensitizing Agents for Photodynamic Therapy

Abstract

International audienceWe report the synthesis of a series of conjugated zinc porphyrin oligomers designed as photodynamic therapy agents. These compounds exhibit exceptionally high two-photon absorption cross-sections, redshifted linear absorption spectra, and high singlet oxygen quantum yields, making them ideal for one-photon- and two-photon-excited photodynamic therapy. These products are substituted by three α-mannose units on each chromophore with the aim to target tumor cells with over-expressing lectin-type membrane receptors

La lumiére pourrait-elle traiter le cancer par interactions lumiére-vivant ?

“…Plusieurs familles de photosensibilisateurs à absorption biphotonique ont été développées au laboratoire. Ces molécules sont efficacement excitées par un laser femtoseconde déclenchant l'effet non linéaire souhaité ce qui permet d'envisager une PDT à deux photons [19,20].…”

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

“…21. 84 They exhibit high two-photon absorption (TPA) properties at wavelengths suitable for biological tissues, which, combined with their high singlet oxygen quantum yields (from 0.43 up to 0.75), makes them promising PS. …”

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

“…Diethylene glycol linkers also found use in Maillard's synthesis of a range of glycosylated zinc dimer/trimer derivatives (418-421) for application in 2-photon absorption PDT [231] . All derivatives were substituted with three α-mannose units on each porphyrin in the hope of targeting tumor cells which contained over-expressed lectin-type membrane receptors.…”

“…Next, the photophysical properties of glycoporphyrins (418, 419, 421) were compared to data of 1PA (one-photon absorption) and 2PA (two-photon absorption) nonglycosylated derivatives (422) [231][232][233] . The 1PA absorption studies of 418 and 419 are very similar to that of 422 and 423, however, all the transitions of the former were slightly blue-shifted compared to the latter pair.…”

“…Another study found that all oligomeric derivatives (418-421) displayed exceptionally high two-photon absorption at wavelengths suitable for biological tissues as well as significantly high singlet oxygen quantum yields (Φ Δ from 0.43 up to 0.75) which make them promising PSs for twophoton excited PDT to treat tumor cells with overexpressing lectin-type receptors [231] . [234] .…”