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Merck

P8293

Protoporphyrin IX

From Porcine, ≥95%, guanylyl cyclase activator, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C34H34N4O4
CAS Number:
553-12-8
Molecular Weight:
562.66
NACRES:
NA.32
PubChem Substance ID:
24278655
UNSPSC Code:
41106305
EC Number:
209-033-7
MDL number:
MFCD00151109
Beilstein/REAXYS Number:
380795

Key Documents

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Product Name

Protoporphyrin IX, ≥95%

InChI key

KSFOVUSSGSKXFI-UJJXFSCMSA-N

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-

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

biological source

Porcine

assay

≥95%

form

powder

solubility

DMF: methanol (1:1): soluble-10 mg/mL, dark red-brown

fluorescence

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

storage temp.

2-8°C

Quality Level

100

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Application

Activates soluble guanylyl cyclase.
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

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.
Protoporphyrin IX levels are elevated in tumor cells due to metabolism anomalies compared to normal cells.

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.
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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN2857
MKCM8113
MKCL8908
MKCL3893
MKCH0349

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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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