5,10,15,20-(tetra-4-hydroxyphenyl)porphyrin - CAS 51094-17-8
Molecular Formula:
C44H30N4O4
Molecular Weight:
678.748
COA:
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Application\Fluorophore:
Ion Indicators and Sensors
Description:
5,10,15,20-(tetra-4-hydroxyphenyl)porphyrin is a porphyrin derivative used for detection of water-soluble vitamins by matrix-assisted laser desorption/ionization (MALDI) mass spectrometry.
Synonyms:
5,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrin
Storage:
Store at -20°C
MSDS:
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InChIKey:
OXBXIINNAXASCM-UHFFFAOYSA-N
InChI:
InChI=1S/C44H30N4O4/c49-29-9-1-25(2-10-29)41-33-17-19-35(45-33)42(26-3-11-30(50)12-4-26)37-21-23-39(47-37)44(28-7-15-32(52)16-8-28)40-24-22-38(48-40)43(36-20-18-34(41)46-36)27-5-13-31(51)14-6-27/h1-24,45-50H
Canonical SMILES:
C1=CC(=O)C=CC1=C2C3=CC=C(N3)C(=C4C=CC(=O)C=C4)C5=CC=C(N5)C(=C6C=CC(=C(C7=CC=C2N7)C8=CC=C(C=C8)O)N6)C9=CC=C(C=C9)O
1.The use of asymmetrical flow field-flow fractionation with on-line detection in the study of drug retention within liposomal nanocarriers and drug transfer kinetics.
Hinna AH1, Hupfeld S2, Kuntsche J1, Brandl M3. J Pharm Biomed Anal. 2016 May 30;124:157-63. doi: 10.1016/j.jpba.2016.02.037. Epub 2016 Mar 2.
Due to their solubilizing capabilities, liposomes (phospholipid vesicles) are suited for designing formulations for intravenous administration of drug compounds which are poorly water-soluble. Despite the good in-vitro stability of such formulations with minimal drug leakage, upon i.v. injection there is a risk of premature drug loss due to drug transfer to plasma proteins and cell membranes. Here we report on the refinement of a recently introduced simple in vitro predictive tool by Hinna and colleagues in 2014, which brings small drug loaded (donor) liposomes in contact with large acceptor liposomes, the latter serving as a model mimicking biological sinks in the body. The donor- and acceptor-liposomes were subsequently separated using asymmetrical flow field-flow fractionation (AF4), during which the sample is exposed to a large volume of eluent which corresponds to a dilution factor of approximately 600. The model drug content in the donor- and acceptor fraction was quantified by on-line UV/VIS extinction measurements with correction for turbidity and by off-line HPLC measurements of collected fractions.
2.Photosensitizer and peptide-conjugated PAMAM dendrimer for targeted in vivo photodynamic therapy.
Narsireddy A1, Vijayashree K2, Adimoolam MG1, Manorama SV1, Rao NM2. Int J Nanomedicine. 2015 Nov 3;10:6865-78. doi: 10.2147/IJN.S89474. eCollection 2015.
Challenges in photodynamic therapy (PDT) include development of efficient near infrared-sensitive photosensitizers (5,10,15,20-tetrakis(4-hydroxyphenyl)-21H,23H-porphine [PS]) and targeted delivery of PS to the tumor tissue. In this study, a dual functional dendrimer was synthesized for targeted PDT. For targeting, a poly(amidoamine) dendrimer (G4) was conjugated with a PS and a nitrilotriacetic acid (NTA) group. A peptide specific to human epidermal growth factor 2 was expressed in Escherichia coli with a His-tag and was specifically bound to the NTA group on the dendrimer. Reaction conditions were optimized to result in dendrimers with PS and the NTA at a fractional occupancy of 50% and 15%, respectively. The dendrimers were characterized by nuclear magnetic resonance, matrix-assisted laser desorption/ionization, absorbance, and fluorescence spectroscopy. Using PS fluorescence, cell uptake of these particles was confirmed by confocal microscopy and fluorescence-activated cell sorting.
3.Reductive dechlorination of atrazine catalyzed by metalloporphyrins.
Nelkenbaum E1, Dror I, Berkowitz B. Chemosphere. 2009 Mar;75(1):48-55. doi: 10.1016/j.chemosphere.2008.11.074. Epub 2009 Jan 18.
Atrazine (2-chloro-4-(ethylamine)-6-(isopropylamine)-s-triazine) is a widely used herbicide which is considered a persistent groundwater contaminant. Its selective transformation mediated by cobalt or nickel porphyrins was studied in aqueous solutions at room temperature and ambient pressure. Several metalloporphyrins were examined as catalysts for the reaction and all yielded the same reaction, transforming atrazine solely to the seldomly reported form 2,4-bis(ethylamine)-6-methyl-s-triazine. The reaction involves dechlorination and migration of a methyl group to yield a symmetric product. Nickel 5,10,15,20-tetrakis(1-methyl-4-pyridinio)porphyrin tetra(p-toluenesulfonate) (TMPyP) was activated by nanosized zero-valent iron (nZVI) while cobalt porphyrins (TMPyP, 5,10,15,20-tetrakis(4-hydroxyphenyl)-21H,23H-porphine-(TP(OH)P) and 4,4',4'',4'''-(porphine-5,10,15,20-tetrayl)tetrakis (benzenesulfonic acid)-(TBSP)) were activated by titanium(III) citrate as the electron donor.
4.Chirality amplification of porphyrin assemblies exclusively constructed from achiral porphyrin derivatives.
Chen P1, Ma X, Duan P, Liu M. Chemphyschem. 2006 Nov 13;7(11):2419-23.
Two achiral porphyrin derivatives, 5,10,15,20-tetrakis(4-methoxyphenyl)-21H,23H-porphine (TPPOMe) and 5,10,15,20-tetrakis(4-hydroxyphenyl)-21H,23H-porphine (TPPOH), were spread onto an air/water interface. The spreading films were transferred onto solid substrates by the Langmuir-Schaefer (LS) method. Although both of the porphyrin derivatives are achiral species, the transferred LS multilayer films shows macroscopic supramolecular chirality, which is suggested to be due to the spontaneous symmetry breaking that occurs at the air/water interface. A strong CD signal is observed from the as-deposited TPPOH LS film, while a relatively weak CD signal is detected from that of TPPOMe. Interestingly, when the TPPOMe LS film was annealed in high vacuum, a significant amplification of the supramolecular chirality is observed. Atomic force microscopy observations confirm that TPPOMe form more ordered aggregates upon annealing. It is suggested that the small amount of chiral assemblies formed in the as-deposited LS film grow into larger ones following the "sergeants and soldiers" principle during the annealing process.
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CAS 51094-17-8 5,10,15,20-(tetra-4-hydroxyphenyl)porphyrin

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