116206-76-9

Basic information

• Product Name: 5,10-bis(4-aminophenyl)-15,20-diiphenylporphyrin
• Synonyms: 5,10-bis(4-aminophenyl)-15,20-diiphenylporphyrin
• CAS NO: 116206-76-9
• Molecular Weight: 644.778
• Mol File: 116206-76-9.mol

Chemical Properties

• CAS DataBase Reference: 5,10-bis(4-aminophenyl)-15,20-diiphenylporphyrin(CAS DataBase Reference)
• NIST Chemistry Reference: 5,10-bis(4-aminophenyl)-15,20-diiphenylporphyrin(116206-76-9)
• EPA Substance Registry System: 5,10-bis(4-aminophenyl)-15,20-diiphenylporphyrin(116206-76-9)

Safety Data

• Hazardous Substances Data: 116206-76-9(Hazardous Substances Data)

Upstream product

• 917-23-7 5,15,10,20-tetraphenylporphyrin 

Downstream Products

• 125964-54-7 C₄₄H₃₀CuN₆ 

Relevant articles and documents

Synthesis and characterization of aminoporphyrin-end-functionalized poly(N-isopropylacrylamide) with photodynamic and thermoresponsive effects

The novel aminoporphyrin-end-functionalized poly(N-isopropylacrylamide) (PNIPAM) polymer H2N-TPP-PNIPAM (TPP=5,10,15,20-tetraphenyl-21H,23H- porphyrin) behaves as a multifunctional platform that displays a photodynamic effect, thermosensitivity

Synthesis and in vitro PDT activity of miscellaneous porphyrins with amino acid and uracil

The synthesis of a series of modularized porphyrins bearing bioactive molecule is described. Starting with meso-tetraphenylporphyrin, the compounds with two nitro functional groups were synthesized via regiospecific nitration reaction. After reduction to the amino group and subsequent coupling with l-phenylalanine or 1-carboxylmethyl-5-fluorouracil (5-Fu acid), the functionalized porphyrins were metallized with Co(II) or Mn(II) to form miscellaneous porphyrins in good yields. The spectra of all the porphyrins were furnished. In vitro photodynamic therapy of the porphyrins against Ec9706 cell line was evaluated by standard cytotoxicity assays.

An alternative approach to amino porphyrins

(Chemical Equation Presented) Modified nitration of tetraphenylporphyrin at para of phenyl with HNO3/Cl3CCOOH and one-pot nitration of free tetraarylporphyrins to metalized 2-nitroporphyrin in high yield are described. A novel reduce

One-pot Synthesis of a Truncated Cone-shaped Porphyrin Macrocycle and Its Self-assembly into Permanent Porous Material

Here, we report the synthesis of a truncated cone-shaped triangular porphyrinic macrocycle, P3L3, via a single step imine condensation of a cis-diaminophenylporphyrin and a bent dialdehyde-based linker as building units. X-ray diffra

(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.

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

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

Synthesis, characterization and in vitro photodynamic antimicrobial activity of basic amino acid-porphyrin conjugates

Photodynamic antimicrobial chemotherapy (PACT), as a novel and effective modality for the treatment of infection with the advantage of circumventing multidrug resistance, receives great attention in recent years. The photosensitizer is the crucial element in PACT, and cationic porphyrins have been demonstrated to usually be more efficient than neutral and negatively charged analogues towards bacteria in PACT. In this work, three native basic amino acids, l-lysine, l-histidine and l-arginine, were conjugated with amino porphyrins as cationic auxiliary groups, and 13 target compounds were synthesized. This paper reports their syntheses, structural characterizations, oil-water partition coefficients, singlet oxygen generation yields, photo-stability, as well as their photo inactivation efficacies against methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli and Pseudomonas aeruginosa in vitro. The preliminary structure-activity relationship was discussed. Compound 4i, with porphyrin bearing four lysine moieties, displays the highest photo inactivation efficacy against the tested bacterial strains at 3.91 1/4M with a low light dose (6 J/cm2), and it is stable in serum and lower cytotoxicity to A929 cells. These basic amino acid-porphyrin conjugates are potential photosensitizers for PACT.

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.

Synthetic strategies towards ruthenium-porphyrin conjugates for anticancer activity

The conjugation of porphyrins to metal fragments is a strategy for making new compounds that are expected to combine the phototoxicity and the tumour-localization properties of the porphyrin chromophore with the cytotoxicity of the metal fragment for additive antitumour effect. We report here the preparation of new classes of porphyrin-ruthenium conjugates with potential bio-medical applications. Ruthenium was chosen because several Ru compounds have shown promising anticancer activity. The conjugation with the porphyrin moiety was accomplished either through peripheral pyridyl rings (e.g.meso-4′-tetrapyridylporphyrin, 4′TPyP) or through bpy units (e.g.meso-(p-bpy-phenyl)porphyrins, bpyn-PPs, n = 1-4). The number of Ru fragments attached to the porphyrins ranges from 1 to 4 and the total charge of the conjugates from -4 to +8. Different types of peripheral fragments, both Ru(iii) and Ru(ii), have been used: in some cases they are structurally similar to established anticancer compounds. Examples are [Na]4[4′ TPyP{trans-RuCl4(dmso-S)}4] (2), that bears four NAMI-type Ru(iii) fragments, or [4′TPyP{Ru([9]aneS3)(en)}4][CF 3SO3]8 (3) and [bpy4-PP{Ru([9]aneS3) (dmso-S)}4][CF3SO3]8 (9) (en = ethane-1,2-diamine, [9]aneS3 = 1,4,7-trithiacyclononane) that have four half-sandwich Ru(ii) compounds. The Ru fragments may either contain one or more labile ligands, such as in 2 or in 9, or be coordinatively saturated and substitutionally inert, such as in 3 or in [bpy4-PP{Ru([12]aneS4)} 4][CF3SO3]8 (11) ([12]aneS4 = 1,4,7,10-tetrathiacyclododecane). Most of the ruthenium-porphyrin conjugates described in this work are soluble - at least moderately - in aqueous solution and are thus suitable for biological investigations, in particular for cytotoxicity and photo-cytotoxicity tests. The Royal Society of Chemistry 2009.