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323497 Sigma-Aldrich

5,10,15,20-Tetrakis(1-methyl-4-pyridinio)porphyrin tetra(p-toluenesulfonate)

Dye content 97 %

Synonym: meso-Tetra(N-methyl-4-pyridyl)porphine tetratosylate salt, TMPyP

  • CAS Number 36951-72-1

  • Empirical Formula (Hill Notation) C72H66N8O12S4

  • Molecular Weight 1363.60

  •  Beilstein/REAXYS Number 6049195

  •  MDL number MFCD00013468

  •  PubChem Substance ID 24859370

  •  NACRES NA.23

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Properties

Related Categories Biochemicals and Reagents, Chelators and Ion Probes, Chelators and Ion Probes for Spectroscopy, Fluorescent Indicators and Probes, Fluorescent Probes, Labels, Particles and Stains,
Quality Level   200
composition   Dye content, 97%
solubility   water: soluble 50 mM(lit.)
λmax   421 nm
SMILES string   Cc1ccc(cc1)S([O-])(=O)=O.Cc2ccc(cc2)S([O-])(=O)=O.Cc3ccc(cc3)S([O-])(=O)=O.Cc4ccc(cc4)S([O-])(=O)=O.C[n+]5ccc(cc5)-c6c7ccc(n7)c(-c8cc[n+](C)cc8)c9ccc([nH]9)c(-c%10cc[n+](C)cc%10)c%11ccc(n%11)c(-c%12cc[n+](C)cc%12)c%13ccc6[nH]%13
InChI   1S/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-,43-38-,44-39-,44-40-;;;;
InChI key   AKZFRMNXBLFDNN-GVHKZQBISA-K

Description

General description

5,10,15,20-Tetrakis(1-methyl-4-pyridinio)porphyrin tetra(p toluenesulfonate) (TMPyP) is a positively charged, two-photon dye, that can bind to DNA in cell cultures and affect the cell viability. Long term encapsulation of TMPyP by nanoparticles is reported to prevent the dye from direct contact with cells, but the dye can still kill the cells via singlet-oxygen production on exposure to infrared light. Nanostructured catalyst of platinum nanoparticles supported on TMPyP functionalized graphene is prepared by hydrothermal polyol process. TMPyP is reported to show excellent ¹O2 luminescence signals on incubation with the fungus, Candida albicans. On photoexcitation, TMPyP undergoes charge-transfer interaction with chemically reduced graphene oxide. It is also reported to be a promising photodynamic therapy photosensitizer.

Application

5,10,15,20-Tetrakis(1-methyl-4-pyridinio)porphyrin tetra(p-toluenesulfonate) (TMPyP), a cationic porphyrin, was used to study the noncovalent functionalization of graphene with cationic porphyrins using UV–vis and fluorescence methods. TMPyP may be used as an optical indicator ligand in the preparation of multifunctional membrane for visual warning and enhanced adsorptive removal of cadmium ions in aqueous solutions. TMPyP was also used to fabricate the (TMPyP)- single-walled carbon nanotubes (SWNT)/sodium copper chlorophyllin-SWNT layer-by-layer film from noncovalently adsorbed composites.

Packaging

100, 250 mg in glass insert

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Novel Graphene‑Based Nanostructures Production, Functionalization, and Engineering

Manuela Melucci,1 Simone Ligi,2 Vincenzo Palermo3* 1ISOF – Consiglio Nazionale delle Ricerche (CNR), Italy 2GNext sas, Italy 3ISOF – Consiglio Nazionale delle Ricerche (CNR), Italy *Email: vincenzo.p...
Keywords: Absorption, Asymmetric synthesis, Catalysis, Deposition, Electronics, Evaporation, Nucleic acid annealing, Oxidations, Reductions, Semiconductor, Silylations, Solvents, Sonication

Sensor Dyes

In 1998 R.F. Furchgott, L.J. Ignarro, and F. Murad received the Nobel Prize in Physiology and Medicine for their discoveries concerning nitric oxide as a signaling molecule in the cardiovascular syst...
Monika Baeumle
BioFiles 2011, 6.3, 23.
Keywords: Applications, Biochemistry, Biological processes, Cancer, Cardiovascular, Central Nervous System, Diseases, Extinction coefficient, Indicators, Inflammation, Methods, Microscopy, Neurotransmission, Sol-gel, Type

Peer-Reviewed Papers
15

References

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