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P8293

Sigma-Aldrich

Protoporphyrin IX

≥95%

Sinônimo(s):

3,7,12,17-Tetramethyl-8,13-divinyl-2,18-porphinedipropionic acid, Kammerer’s porphyrin, Ooporphyrin

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About This Item

Fórmula empírica (Notação de Hill):
C34H34N4O4
Número CAS:
Peso molecular:
562.66
Beilstein:
380795
Número CE:
Número MDL:
Código UNSPSC:
41106305
ID de substância PubChem:
NACRES:
NA.32

Ensaio

≥95%

forma

powder

fluorescência

λex 402 nm; λem 625 nm (bound to HRP)
λex 409 nm; λem 633 nm

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

Cc1c(CCC(O)=O)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(C)c5C=C)c(C)c4C=C)c(C)c3CCC(O)=O

InChI

1S/C34H34N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-

chave InChI

KSFOVUSSGSKXFI-UJJXFSCMSA-N

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Descrição geral

Protoporphyrin IX belongs to the porphyrin family, which are a class of tetrapyrroles. It is the iron-free form of hemin and amphiphilic in nature. It is the precursor of heme in its biosynthetic pathway.
Protoporphyrin IX imparts red color to heme and is the major porphyrin in blood. It is synthesized from protoporphyrinogen IX in the presence of protoporphyrinogen IX oxidase.

Aplicação

Protoporphyrin IX has been used:
  • as a standard in protoporphyrin assays
  • in fluorescence spectra analysis
  • to treat cells in cell culture to study heme-mediated ferroportin 1 transcription
Activates soluble guanylyl cyclase.

Ações bioquímicas/fisiológicas

Protoporphyrin IX penetrates human erythrocytes and aids the release of oxygen from them. It forms complexes with myoglobin and hemoglobin. It is a photosensitizer used in the photodynamic therapy of cancer.
Protoporphyrin IX levels are elevated in tumor cells due to metabolism anomalies compared to normal cells.

Pictogramas

Exclamation mark

Palavra indicadora

Warning

Frases de perigo

Classificações de perigo

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves


Certificados de análise (COA)

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Visite a Biblioteca de Documentos

Intrinsic fluorescence of protoporphyrin IX from blood samples can yield information on the growth of prostate tumours
de Oliveira Silva FR, et al.
Journal of Fluorescence, 20(6), 1159-1165 (2010)
Aggregation Behavior of Protoporphyrin IX in Aqueous Solutions: Clear Evidence of
Vesicle Formation
Luigi Monsu Scolaro
The Journal of Physical Chemistry B, 106, 2453-2459 (2002)
Takafumi Nakano et al.
PloS one, 13(6), e0198345-e0198345 (2018-06-02)
Porphyria cutanea tarda (PCT), the most common of the human porphyrias, arises from a deficiency of uroporphyrinogen decarboxylase. Studies have shown a high prevalence of hepatitis C virus (HCV) infection in patients with PCT. While these observations implicate HCV infection
Fluorescent cancer-selective alkylphosphocholine analogs for intraoperative glioma detection.
Swanson KI
Neurosurgery, 76(2), 115-123 (2015)
Ki Mo Kim et al.
Environmental toxicology and pharmacology, 48, 85-93 (2016-10-23)
Coniferaldehyde (CA) exerts anti-inflammatory properties by inducing heme oxygenase-1 (HO-1). To define the regulation mechanism by which CA induces a cytoprotective function and HO-1 expression, the up-stream regulations involved in the activation of nuclear transcription factor-erythroid 2-related factor (Nrf)-2/HO-1 pathway

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