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Merck

P8293

Sigma-Aldrich

Protoporphyrin IX

≥95%

Sinónimos:

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 (notación de Hill):
C34H34N4O4
Número de CAS:
Peso molecular:
562.66
Beilstein/REAXYS Number:
380795
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.32
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Quality Level

assay

≥95%

form

powder

fluorescence

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

storage temp.

2-8°C

SMILES string

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-

InChI key

KSFOVUSSGSKXFI-UJJXFSCMSA-N

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General description

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.[1][2][3]
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.[4]

Application

Activates soluble guanylyl cyclase.
Protoporphyrin IX has been used:
  • as a standard in protoporphyrin assays[5]
  • in fluorescence spectra analysis[6]
  • to treat cells in cell culture to study heme-mediated ferroportin 1 transcription[7]

Biochem/physiol Actions

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.[1][2]
Protoporphyrin IX levels are elevated in tumor cells due to metabolism anomalies compared to normal cells.[4]

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Referencia del producto
Descripción
Precios

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Visite la Librería de documentos

Feng Liu et al.
Sensors (Basel, Switzerland), 18(6) (2018-06-03)
A label-free sensing platform is developed based on switching the structure of aptamer for highly sensitive and selective fluorescence detection of ochratoxin A (OTA). OTA induces the structure of aptamer, transforms into G-quadruplex and produces strong fluorescence in the presence
Agata Szade et al.
EMBO molecular medicine, 11(12), e09571-e09571 (2019-11-12)
Granulocyte colony-stimulating factor (G-CSF) is used in clinical practice to mobilize cells from the bone marrow to the blood; however, it is not always effective. We show that cobalt protoporphyrin IX (CoPP) increases plasma concentrations of G-CSF, IL-6, and MCP-1
Heme controls ferroportin1 (FPN1) transcription involving Bach1, Nrf2 and a MARE/ARE sequence motif at position -7007 of the FPN1 promoter.
Marro S
Haematologica, 95(8), 1261-1268 (2010)
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)

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