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323497

Sigma-Aldrich

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

Dye content 90 %

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C72H66N8O12S4
CAS Number:
Molecular Weight:
1363.60
Beilstein:
6049195
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23

form

powder

composition

Dye content, 90%

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

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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sharif M Abdelghany et al.
Biomacromolecules, 14(2), 302-310 (2013-01-19)
meso-Tetra(N-methyl-4-pyridyl) porphine tetra tosylate (TMP) is a photosensitizer that can be used in photodynamic therapy (PDT) to induce cell death through generation of reactive oxygen species in targeted tumor cells. However, TMP is highly hydrophilic, and therefore, its ability to
Aleksandra Wojcik et al.
ACS nano, 4(11), 6697-6706 (2010-10-30)
Photoexcited cationic 5,10,15,20-tetrakis(1-methyl-4-pyridinio)porphyrin tetra(p-toluenesulfonate) (TMPyP) undergoes charge-transfer interaction with chemically reduced graphene oxide (RGO). Formation of the ground-state TMPyP-RGO complex in solution is marked by the red-shift of the porphyrin absorption band. This complexation was analyzed by Benesi-Hildebrand plot. Porphyrin
Marina K Kuimova
Physical chemistry chemical physics : PCCP, 14(37), 12671-12686 (2012-07-19)
This article describes an emerging method for quantitative measurement and spatial imaging of microviscosity within individual domains of live cells. The method is based on fluorescence detection from small synthetic molecules termed 'molecular rotors', which are characterised by a strong
Development of a multifunctional membrane for chromatic warning and enhanced adsorptive removal of heavy metal ions: Application to cadmium.
Zhang L, et al.
Journal of Membrane Science, 379(1), 69-79 (2011)
Enhanced photocurrent generation in nanostructured chromophore/carbon nanotube hybrid layer-by-layer multilayers.
Baba A, et al.
The Journal of Physical Chemistry C, 114(35), 14716-14721 (2010)

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