Size-controlled assemblies of porphyrin-modified pullulan photosensitizers

Abstract

Pullulan conjugates (i.e. PFP1, PFP4) formed via DCC/DMAP coupling of porphyrin derivatives possessing one (P1) or four (P4) carboxylic acid moieties with folate-appended pullulans (PF) were prepared for application as photosensitizers (PS) for photodynamic therapy. To maximize the desired PS characteristics, the assembly size of PS should be less than 200 nm in water medium. In a PBS buffer solution, PFP4 forms smaller assemblies (~100 nm) than PFP1 (~320 nm) due to its enhanced intramolecular hydrophilicity.

Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics

“…This was attributed due to the core tetrakis(4-carboxyphenyl)porphyrin molecule, which is more hydrophilic with three extra carboxylic groups as compared to 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin. 363 Drasar and co-workers reported the aggregation of a series of glycosylated porphyrins with glycosylated groups directly attached to the meso position via a C atom linkage, and 5,15diglycosylated compounds with 10,20-meso-perfluorophenyl groups in mixed solvent systems such as DMF−water, DMSO−water, and CH 3 CN−water. 118,177 These studies indicate that the self-aggregation of sugar porphyrins also depends on the position of sugar moiety attached.…”

“…This was attributed due to the core tetrakis(4-carboxyphenyl)-porphyrin molecule, which is more hydrophilic with three extra carboxylic groups as compared to 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin. 363 …”

“…They observed a smaller aggregate (∼100 nm) for tetrakis­(4-carboxyphenyl)­porphyrin-pullulan conjugate as compared to the other conjugate (∼320 nm). This was attributed due to the core tetrakis­(4-carboxyphenyl)­porphyrin molecule, which is more hydrophilic with three extra carboxylic groups as compared to 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin …”

Enhanced in vitro photocytotoxicity of water-soluble dendritic pheophorbide-a

“…S3). Particle sizes of >200 nm can be problematic in PDT applications due to the resulting insufficient circulation time in the bloodstream [26]. As shown in Fig.…”