127822-97-3

Upstream product

• 872-85-5 pyridine-4-carbaldehyde 
• 109-97-7 pyrrole 
• 123-08-0 4-hydroxy-benzaldehyde 
• 139547-52-7 5-(4-pyridyl)10,15,20-tri(p-anisyl)porphyrin 

Relevant academic research and scientific papers

The synthesis and photodynamic properties of meso-substituted, cationic porphyrin derivatives in HeLa cells

A series of asymmetric porphyrins with varying substituents, such as 4-hydrophenyl and N-methyl-4-pyridyl, were synthesized and characterized and their cell uptake, intracellular localization, cytotoxicities and phototoxicities were evaluated in vitro. The most phototoxic of the porphyrins synthesized, 5,10-di-(N-methyl-4-pyridyl)-15,20-(4-hydroxyphenyl)-21,23H-porphyrin, which was mainly localized in the mitochondria and displayed low levels of dark toxicity toward human cancer HeLa cells, offers potential application in photodynamic therapy.

Synthesis of Porphyrinyl-Nucleosides

Several porphyrinyl-nucleosides were prepared in the reaction of the OH group of one, two or four meso-p-hydroxyphenyl substituents of porphyrin with 5'-O-tosylates of 2',3'-O-isopropylidene-adenosine or -uridine, or 5'-O-tosylthymidine; the remaining porphyrin meso-substituents were p-tolyl, p-hydroxyphenyl or 4-pyridyl.The following porphyrinyl-nucleosides were obtained with 8-17percent yield: meso-di(p-tolyl)di(p-phenylene-5'-O-2',3'-O-isopropylidene-adenosine) (or -uridine)porphyrins 1,2, the respective meso-tetranucleosideporphyrins 3,4-meso-mono(p-phenylene-5'-O-thymidine)porphyrins 5-7, meso-di(p-tolyl)di(p-phenylene-5'-O-thymidine)porphyrins 8,9 and the meso-di(p-hydroxyphenyl)di(p-phenylene-5'-O-thymidine)porphyrins 10.Other compounds prepared belonged to the series: meso(4-pyridyl)4-n(p-phenylene-5'-O-2',3'-O-isopropylideneuridine)nporphyrin, n = 1,2 or 4, 11-13.N-Methylation gave the water soluble iodide salts: (N-methyl-4-pyridinium)4-n(p-phenylene-5'-O-2',3'-isopropylideneuridine)nporphyrins, n = 1,2 or 4, 14-16.The ms fab showed in most cases stepwise detachment of the CH2(5')-nucleoside fragments.The porphyrins meso disubstituted by thymidine represent a convenient substrate for the build-up of both nucleoside units into the oligo/polynucleotide chains.

Porphyrinyl-uridines as the First Water Soluble Porphyrinyl-nucleosides

Meso-derivatives of porphine containing N-methyl-4-pyridinium and 5'-O-p-phenylene-2',3'-O-protected-uridine substituents were obtained as the first representatives of water soluble porphyrinyl-nucleosides.