36951-72-1

Basic information

• Product Name: TMPYP
• Synonyms: 5,10,15,20-TETRAKIS-(N-METHYL-4-PYRIDYL)-21,23H-PORPHYRIN TETRATOSYLATE;5,10,15,20-TETRAKIS (1-METHYL-4-PYRIDINIO) PORPHINE TETRA (P-TOLUENESULFONATE);5,10,15,20-TETRAKIS(1-METHYL-4-PYRIDINIO)-PORPHYRIN TETRA(P-TOLUENESULFONATE);5,10,15,20-TETRAKIS(1-METHYL-4-PYRIDINIO)PORPHYRIN TETRA(TOLUENE-4-SULFONATE);5,10,15,20-TETRAKIS(1-METHYL-4-PYRIDYL)-21H,23H-PORPHINE, TETRA-P-TOSYLATE SALT;ALPHA,BETA,GAMMA,DELTA-TETRAKIS(1-METHYLPIRIDINIUM-4-YL)PORPHINE P-TOLUENESULFONATE;ALPHA,BETA,GAMMA,DELTA-TETRAKIS(1-METHYLPYRIDINIUM-4-YL)PORPHINE P-TOLUENESULFONATE;MESO-TETRA-(1-METHYL-4-PYRIDINIO)PORPHYRIN TETRATOSYLATE
• CAS NO: 36951-72-1
• Molecular Formula: 4C₇H₇O₃S*C₄₄H₃₈N₈
• Molecular Weight: 1363.6
• Product Categories: Porphyrins;Synthetic Porphyrins;Analytical Chemistry;Biochemistry;Chelating Reagents;Ligands for Pharmaceutical Research;Magnetic Resonance Imaging (Chelating Reagents);Porphines;Pyridinium Compounds
• Mol File: 36951-72-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: >300℃
• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: water: soluble50MM(lit.)
• BRN: 6049195
• CAS DataBase Reference: TMPYP(CAS DataBase Reference)
• NIST Chemistry Reference: TMPYP(36951-72-1)
• EPA Substance Registry System: TMPYP(36951-72-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• F: 3-8-10
• Hazardous Substances Data: 36951-72-1(Hazardous Substances Data)

Usage

Description

TMPyP, also known as 5,10,15,20-Tetrakis(1-methyl-4-pyridinio)porphyrin tetra(p toluenesulfonate), is a positively charged, two-photon dye that can bind to DNA in cell cultures and affect cell viability. It is an organosulfonate salt that is the tetrakis(p-toluenesulfonate) salt of meso-tetrakis(N-methyl-4-pyridyl)porphine. TMPyP has been reported to show excellent 1O2 luminescence signals on incubation with the fungus, Candida albicans, and is also used in photodynamic therapy as a photosensitizer.

Uses

Used in Anticancer Applications:
TMPyP is used as a telomerase inhibitor for its potent inhibitory effect on telomerase activity, which is essential for the uncontrolled growth of cancer cells.
Used in Photodynamic Therapy:
TMPyP is used as a photosensitizer for its ability to produce singlet-oxygen on exposure to infrared light, which can kill cells and is a promising approach in photodynamic therapy.
Used in Drug Delivery Systems:
TMPyP is used as a component in the development of novel drug delivery systems, such as nanostructured catalysts of platinum nanoparticles supported on TMPyP functionalized graphene, to enhance the delivery, bioavailability, and therapeutic outcomes of various treatments.
Used in Cell Culture Research:
TMPyP is used as a two-photon dye for binding to DNA in cell cultures, allowing researchers to study the effects of the dye on cell viability and other cellular processes.
Used in Fungal Research:
TMPyP is used in the study of Candida albicans, as it shows excellent 1O2 luminescence signals on incubation with the fungus, providing valuable insights into its interactions and potential applications in antifungal treatments.

InChI:InChI=1/C44H37N8.4C7H8O3S/c1-49-21-13-29(14-22-49)41-33-5-7-35(45-33)42(30-15-23-50(2)24-16-30)37-9-11-39(47-37)44(32-19-27-52(4)28-20-32)40-12-10-38(48-40)43(36-8-6-34(41)46-36)31-17-25-51(3)26-18-31;4*1-6-2-4-7(5-3-6)11(8,9)10/h5-28H,1-4H3,(H,45,46,47,48);4*2-5H,1H3,(H,8,9,10)/q+3;;;;/p-3/b41-33-,41-34-,42-35-,42-37-,43-36-,43-38u,44-39u,44-40-;;;;

Upstream product

• 80-48-8 methyl p-toluene sulfonate 
• 16834-13-2 5,10,15,20-tetra(4-pyridyl)-21H,23H-porphine 

Downstream Products

• 92739-63-4 5,10,15,20-tetrakis(4-methylpyridinium)porphyrin tetrahydrochloride 

Relevant articles and documents

Electrocatalytic water oxidation by a water-soluble nickel porphyrin complex at neutral ph with low overpotential

The water-soluble cationic nickel(II) complex of meso-tetrakis(4-N-methylpyridyl)porphyrin (1) can electrocatalyze water oxidation to O2 in neutral aqueous solution (pH 7.0) with the onset of the catalytic wave appearing at 14;1.0 V (vs NHE). The homogeneous catalysis with 1 was verified. Catalyst 1 exhibited water oxidation activity in a pH range 2.0-8.0 and had a strict linear dependence of catalytic current on its concentration. After 10 h of constant potential electrolysis at 1.32 V (vs NHE), a negligible difference of the solution was observed by UV-vis. In addition, inspection of the working electrode by electrochemistry, scanning electron microscope (SEM), and energy dispersive X-ray spectroscopy (EDX) showed no sign of deposition of NiOx films. These results strongly argued that 1 is a real molecular electrocatalyst for water oxidation. The turnover frequency (TOF) for this process was 0.67 s-1 at 20 °C. On the basis of results from the kinetic isotope effect (KIE) and inhibition experiments, electrochemical studies in various buffer solutions with different anions and pHs, and DFT calculations, a catalytic cycle of 1 for water oxidation via a formally Ni(IV) species was proposed.

Pulsed Irradiation of Water-soluble Porphyrins

Nanosecond laser flash photolysis and pulse radiolysis have been used to characterise the excited states and radicals of meso-tetraphenylporphyrin tetrasulphonic acid as the tetrasodium salt (Na4TPPS) and of meso-tetra-N-methylpyridylporphyrin as the tetra-p-toluenesulphonate (TMPyrP).After 347 nm irradiation, aqueous Na4TPPS forms triplet states (ΦT=0.76) and photoionises monophotonically (ΦI=0.029), while TMPyrP forms only triplets (ΦT=0.92) and does not photoionise.The difference and corrected spectra of the triplet states and the semi-oxidised and semi-reduced radicals of these molecules have been obtained.