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

Properties

• Product Name: Protoporphyrin IX, ≥95%
• biological source: Porcine
• Quality Level: 100
• Assay: ≥95%
• form: powder
• solubility: DMF: methanol (1:1): soluble-10 mg/mL, dark red-brown
• fluorescence: λ_ex 402 nm; λ_em 625 nm (bound to HRP); λ_ex 409 nm; λ_em 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

Description

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]

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• 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