65952-93-4

Upstream product

• 22112-84-1 tetrakis(4-aminophenyl)porphyrin 
• 74-88-4 methyl iodide 
• 14945-24-5 N,N-dimethyl-4-[(5,10′,14′′,19′′′ )-10,15,20-tris(4-dimethylaminophenyl)-21,23-dihydroporphyrin-5-yl]aniline 

Downstream Products

• 99397-69-0 C₅₆H₆₂N₈⁽⁴⁺⁾*C₄₄H₂₆N₄O₁₂S₄^(4-) 

Relevant academic research and scientific papers

Palladium(II) tetrakis(4-N,N,N-trimethylammoniumphenylene)porphyrin supported on ion-exchange resins as efficient and reusable catalysts for C-C coupling reactions

In this research, the Heck and Suzuki reactions catalyzed by tetrakis(4-N,N,N-trimethylammoniumphenylene)porphyrinatopalladium(II) iodide, [Pd(TTMAPP)]I4, immobilized on ion-exchange resins such as Dowex 50 WX8 and Amberlite IR-120 are reported. In this manner, first, tetrakis(4-N,N-dimethylaminophenylene)porphyrin was converted to tetrakis(4-N,N,N-trimethylammoniumphenylene)porphyrin iodide, [H 2TTMAPP]I4, with methyl iodide. Then this water soluble porphyrin was metalated by palladium(II) chloride and the [Pd(TTMAPP)]I 4 was produced. This cationic palladium porphyrin was immobilized onto the ionic supports via electrostatic interactions. The catalysts, [Pd(TTMAPP)]@Dowex 50 WX8 and [Pd(TTMAPP)]@Amberlit IR-120, were characterized by FT-IR and diffuse reflectance UV-Vis spectroscopic methods, and scanning electron microscopy. These heterogeneous catalysts are thermally stable, oxygen insensitive, phosphine-free, air- and moisture-stable in the C-C coupling reactions and are reusable several times without significant loss of their catalytic activity.

Effect of overall charge and charge distribution on cellular uptake, distribution and phototoxicity of cationic porphyrins in HEp2 cells

Five cationic porphyrins bearing one to four -N(CH3)3+ groups linked to the p-phenyl positions of 5,10,15,20-tetraphenylporphyrin (TPP) were synthesized in order to study the effect of overall charge and its distribution on the cellular uptake, phototoxicity and intracellular localization using human carcinoma HEp2 cells. The di-cationic porphyrins DADP-o and DADP-a accumulated the most within cells and preferentially localize within vesicular compartments and in mitochondria. Of these two only DADP-a was phototoxic to the cells (IC50=3μM at 1J/cm2). The mono-cationic porphyrin MAP was found to be the most phototoxic of the series, and it localized mainly in lipid membranes, including the plasma membrane, ER, mitochondria, and Golgi. Both the tri-cationic porphyrin TRAP and the tetra-cationic porphyrin TEAP localized subcellularly mainly in the mitochondria, but of the two only TEAP showed moderate phototoxicity (IC50=8μM at 1J/cm2). Our results suggest that MAP is the most promising PDT photosensitizer, and that both DADP-o and TRAP might find application as transport vehicles for therapeutics into cells.

Synthesis of tetraphenylporphins with reactive groups in the phenyl rings. 7. Salts of tetrakis(N,N,N-trimethylaminophenyl)porphins

Tetrakis(N,N-dimethylaminophenyl)porphins and water-soluble salts of tetrakis(N,N,N-tnmelhylaminophenyl)porphins have been obtained by the alkylation of tetrakis(aminophenyl)porphins with methyl iodide. 1996 Plenum Publishing Corporation.