127800-97-9

Upstream product

• 872-85-5 pyridine-4-carbaldehyde 
• 109-97-7 pyrrole 
• 122-85-0 para-acetamidobenzaldehyde 
• 71188-40-4 5,10,15-tris(4'-pyridyl)-20-(phenyl)porphyrin 

Relevant academic research and scientific papers

NMR Study of Hyperporphyrin Effects in the Protonations of Porphyrins with 4-Aminophenyl and 4-Pyridyl Meso Substituents

Titrations for a series of porphyrins bearing either 4-aminophenyl or 4-pyridyl meso substituents were performed using methanesulfonic acid in DMSO and followed by proton NMR. Special emphasis was placed on identifying the intermediate protonation stages that are described as hyperporphyrins, that is, where there exist strong charge-transfer interactions between the peripheral aminophenyl groups and the protonated porphyrin ring. In particular, evidence was gathered to support the significance of a novel resonance form involving charge transfer between two peripheral substituents, an aminophenyl group and a protonated pyridinium group. 1H NMR and NOESY spectra provide evidence for the importance of such resonance effects in the triply protonated triamino/monopyridyl hyperporphyrin (A3PyPH3+3).

Synthesis, DNA binding and cancer cell toxicity of Cu(II)-complexes of a tricationic nitro-porphyrin or analogous porphyrins with pendant Schiff bases derived from reduction of the nitro group

Three Cu-complexes, one is containing 5-(4-Nitrophenyl)-10,15,20-tris (4-N-methylpyridinium) porphyrin ligand (labeled as CuP-1) and the others with meso-10,15,20-tris (4-N-methylpyridinium)-5-(4′-X-schiff base) porphyrin ligands (X referred to salicylald

Comparison of photo-oxidation reactions in batch and a new photosensitizer-immobilized microfluidic device

A glass microfluidic device has been functionalized with photoactive porphyrins for performing reactions which are mediated by singlet molecular oxygen. The resulting device was used to investigate the photochemical oxidation of cholesterol, α-terpinene, and citronellol under flow conditions, and the results were compared with similar batch reactions.

Photophysical and bactericidal properties of pyridinium and imidazolium porphyrins for photodynamic antimicrobial chemotherapy

Despite advances achieved over the last decade, infections caused by multi-drug-resistant bacterial strains are increasingly becoming important societal issues that need to be addressed. New approaches have already been developed in order to overcome this problem. Photodynamic antimicrobial chemotherapy (PACT) could provide an alternative to fight infectious bacteria. Many studies have highlighted the value of cationic photosensitizers in order to improve this approach. This study reports the synthesis and the characterization of cationic porphyrins derived from methylimidazolium and phenylimidazolium porphyrins, along with a comparison of their photophysical properties with the well-known N-methylpyridyl (pyridinium) porphyrin family. PACT tests conducted with the tetracationic porphyrins of these three families showed that these new photosensitizers may offer a good alternative to the classical pyridinium porphyrins, especially against S.aureus and E.coli. In addition, they pave the way to new cationic photosensitizers by the means of derivatization through amide bond formation.

Hyperporphyrin effects in the spectroscopy of protonated porphyrins with 4-aminophenyl and 4-pyridyl meso substituents

Spectrophotometric titrations for a full series of 4-aminophenyl/4-pyridyl meso-substituted porphyrins were carried out using methanesulfonic acid in DMSO to study the hyperporphyrin effect across different substitution patterns. The series included zero, one, two (cis and trans), three, and four meso(4-aminophenyl) groups, with the remaining meso substituents being 4-pyridyl groups. The peripheral pyridyl groups consistently protonate before the interior porphyrin pyrrole nitrogens, which protonate before the aminophenyl groups. Aminophenyl substituents increase the basicity of the pyrrole nitrogens and lead to distinctive hyperporphyrin spectra with a broad Soret band and a strong red absorption. The structure proposed to give rise to these spectra is the previously proposed charge-transfer interaction between the aminophenyl and the protonated pyrrole. A novel hyperporphyrin structure involving charge-transfer interactions between two peripheral substituents is also proposed in one case, the triply protonated (+3) porphyrin with three aminophenyls and one pyridyl substituent; two of the aminophenyl groups delocalize the charges on the interior nitrogens, while the third aminophenyl group delocalizes with the protonated pyridyl.

Towards sequence selective DNA binding: Design, synthesis and DNA binding studies of novel bis-porphyrin peptidic nanostructures

A new series of peptidic nanostructures bearing two intercalating moieties was designed and synthesized to achieve selective recognition of DNA sequences. A cationic porphyrin was attached to a glutamic acid side chain and the latter introduced into a pep

The synthesis of new potential photosensitizers [1-3]. Part 4. Photophysical properties of some monophenyltripyridyl-porphyrin derivatives

Six monophenyltripyridylporphyrin derivatives were synthesized and characterized by spectroscopy in order to demonstrate their potential usefulness as photosensitizers for anticancer therapy purposes. Compounds 1 and 3-5 are amphiphilic, thus they may be

Enantioselective recognition of dicarboxylic acid guests based on an allosteric effect of a chiral double-decker porphyrin which changes the stoichiometry upon the guest binding

A double-decker porphyrin 1R bearing one chiral substituent per porphyrin ring was synthesised. The host 1R showed highly cooperative binding towards chiral guest 2R with stoichiometry of the complex (1:2) and its stepwise association constants (K1 and K2

Mesoporous silicon nanoparticles for targeted two-photon theranostics of prostate cancer

A novel non-toxic porous silicon nanoparticle grafted with a mannose-6-phosphate analogue and applicable in 2-photon imaging and photodynamic therapy was specifically designed for targeting prostate cancer cells.

Synthesis of a porphyrin with histidine-like chelate: an efficient path towards molecular PDT/SPECT theranostics

The goal of “personalised” medicine has seen a growing interest in the development of theranostic agents. Bifunctional, and targeted-trifunctional, theranostic water-soluble porphyrins with a histidine-like chelating group have been synthesisedviacopper-catalysed azide-alkyne cycloaddition (CuAAC) “click” chemistry in high yield and purity. They are capable of photodynamic treatment and [99mTc(CO)3]+complexation for single-photon emission computed tomography (SPECT) imaging, with a radiochemical yield of >95%. The toxicity and phototoxicity were evaluated on HT-29 cells, DU145, and DU145-PSMA cell lines, with the targeted theranostic showing more potent phototoxicity towards DU145-PSMA expressing cells.