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Usage

Uses

Used in Sensor Applications:
5,15-Di(4-aminophenyl)-10,20-diphenyl porphine is used as a sensing agent for its ability to interact with various molecules, which can lead to changes in its electronic properties. This characteristic makes it a promising candidate for the development of chemical and biological sensors.
Used in Imaging Probe Applications:
In the field of medical imaging, 5,15-Di(4-aminophenyl)-10,20-diphenyl porphine is used as an imaging probe due to its light-absorbing properties. It can be utilized in techniques such as fluorescence imaging and photoacoustic imaging to visualize biological structures and processes.
Used in Photodynamic Therapy:
5,15-Di(4-aminophenyl)-10,20-diphenyl porphine is used as a photosensitizer in photodynamic therapy for its capacity to absorb light and generate reactive oxygen species. This application is particularly relevant in the treatment of cancer, where the reactive species can cause damage to cancerous cells while sparing healthy tissue.
Used in Research and Development:
Due to its complex synthesis and the ongoing investigation of its potential applications, 5,15-Di(4-aminophenyl)-10,20-diphenyl porphine is also used in research and development settings to explore new methods of synthesis and to understand its interactions with biological systems and other molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5,15-Di(4-aminophenyl)-10,20-diphenyl porphine is used as a precursor or building block in the development of new drugs that may leverage its unique electronic and binding properties for targeted therapies or diagnostics.

Upstream product

• 917-23-7 5,15,10,20-tetraphenylporphyrin 
• 555-16-8 4-nitrobenzaldehdye 
• 143859-77-2 2,2'-[(4-nitrophenyl)methylene]bis(1H-pyrrole) 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

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.

Self-assembly of a donor-acceptor nanotube. a strategy to create bicontinuous arrays

The self-assembly of bolaamphiphile 1 into nanotubes containing a nanostructured electron donor/acceptor heterojunction is reported. In 10% MeOH/H2O, the tetraphenylporphyrin (TPP) and 1,4,5,8- naphthalenetetracarboxylic acid diimide chromophor

A Redox Stimulation-Activated Amphiphile for Enhanced Photodynamic Therapy

The development of more efficient photosensitizers with minimal damage to surrounding normal tissues has been a valuable and challenging subject during photodynamic therapy (PDT). Herein, a stimuli-activated porphyrinic photosensitizer (PEG-TPP-DNB; PEG =

(Aminophenyl)porphyrins as precursors for the synthesis of porphyrin-modified siloxanes

The present research reports the efficient synthesis of mono- and di-(aminophenyl)porphyrins and their metalation with Zn(II) using microwave irradiation. The subsequent reaction of amino-functionalized porphyrins with siloxane moieties bearing epoxy or carboxyl functional groups provided four new porphyrin-modified siloxanes. The structure of the resulting derivatives was established by 1H-NMR and MALDI-TOF-MS. The optical properties of the porphyrin chromophores were preserved, as proven by comparing the absorption and emission spectra of the initial porphyrins to those of the porphyrin-modified siloxanes.

Steering on-surface polymerization with metal-directed template

On-surface polymerization represents a novel bottom-up approach for producing macromolecular structures. To date, however, most of the structures formed using this method exhibit a broad size distribution and are disorderly adsorbed on the surface. Here we demonstrate a strategy of using metal-directed template to control the on-surface polymerization process. We chose a bifunctional compound which contains pyridyl and bromine end groups as the precursor. Linear template afforded by pyridyl-Cu-pyridyl coordination effectively promoted Ullmann coupling of the monomers on a Au(111) surface. Taking advantage of efficient topochemical enhancement owing to the conformation flexibility of the Cu-pyridyl bonds, macromolecular porphyrin structures that exhibit a narrow size distribution were synthesized. We used scanning tunneling microscopy and kinetic Monte Carlo simulation to gain insights into the metal-directed polymerization at the single molecule level. The results reveal that the polymerization process profited from the rich chemistry of Cu which catalyzed the C-C bond formation, controlled the size of the macromolecular products, and organized the macromolecules in a highly ordered manner on the surface.

Porphyrin chemistry pertaining to the design of anti-cancer drugs; part 1, the synthesis of porphyrins containing meso-pyridyl and meso-substituted phenyl functional groups

Condensation of pyrrole with a benzaldehyde and 4-pyridinecarboxaldehyde mixture yields the six possible meso-substituted phenyl or pyridyl porphyrins. Nitration of four of these has yielded 13 other porphyrins containing one to four 4-nitrophenyl moieties, and SnCl2 reduction of eight of these nitrophenylporphyrins gives the corresponding 4-aminophenyl(phenyl)- or 4-aminophenyl(phenyl)(4-pyridyl)-porphyrins. Twelve of the porphyrins are new, but all 27 are fully characterized by 1H NMR; resonances for every proton within each of the phenyl, pyridyl, and pyrrole rings are assigned. Trends in UV-VIS data are discussed, while IR and mass spectral data are noted for selected porphyrins. Condensation of pyrrole with a benzaldehyde and 4-pyridinecarboxaldehyde mixture yields the six possible meso-substituted phenyl or pyridyl porphyrins. Nitration of four of these has yielded 13 other porphyrins containing one to four 4-nitrophenyl moieties, and SnCl2 reduction of eight of these nitrophenylporphyrins gives the corresponding 4-aminophenyl(phenyl)- or 4-aminophenyl(phenyl)(4-pyridyl)-porphyrins. Twelve of the porphyrins are new, but all 27 are fully characterized by 1H NMR; resonances for every proton within each of the phenyl, pyridyl, and pyrrole rings are assigned. Trends in UV-VIS data are discussed, while IR and mass spectral data are noted for selected porphyrins.

Syntheses and photophysical properties of diaminotetraphenylporphyrins and their corresponding polyimides

Two free base porphyrins, 5,10-bis(4-aminophenyl)-15,20-diphenylporphyrin (cis-DATPP), 5,15-bis(4-aminophenyl)-10,20-diphenylporphyrin (trans-DATPP), and their zinc metalated analogues (cis-ZnDATPP and trans-ZnDATPP) were synthesized. A series of their co

Water-soluble sulfonate porphyrin functionalized hyaluronic acid with comb-like structure: Potential photosensitizers for photodynamic therapy

A water-soluble comb-like porphyrin polymer based on hyaluronic acid (HA) as the main chain and sulfonate substituted tetraphenylporphyrin (TASP) as side groups, named as HA-g-NH-TPP-(SO3Na) [(HA-g-TASP)], was designed and synthesized, which co

Selenoxide elimination manipulate the oxidative stress to improve the antitumor efficacy

Selenoxide elimination reaction has been widely used in the field of organic synthesis. However, few studies have been conducted to apply this reaction in biodegradable nanomedicine. In this work, the selenoxide elimination reaction was used for cancer tr

Synthesis and photophysical properties of sulfonamidophenyl porphyrins as models for activatable photosensitizers

(Chemical Equation Presented) The ability to localize agents to specific anatomic sites remains an important aspect in designing more efficient therapeutics. Light-activated therapies, in particular, allow for the focal ablation of target tissues and cells. In order to increase the specificity of these agents, stimuli-activated systems have been developed, which are nonphototoxic in the absence of activation. To this end, we propose a novel paradigm for excited state quenching and activation based upon the direct conjugation of quenching moieties to the porphyrinic macrocycle. Model compounds, based upon meso-(p-aminophenyl)porphyrins were synthesized bearing 1 to 4 sulfonamide-linked 2,4-dinitrobenzene. The singlet oxygen and fluorescence quantum yields of these compounds were obtained and compared, as well as the kinetics of activation with relevant activating agents. In addition, methods were developed to further modify the porphyrin in order to modulate the polarity and effect conjugation to biomolecules or nanoparticulate scaffolds. These systems may prove useful in the treatment of a number of disease states, such as cancer and bacterial infection.