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MedKoo Cat#: 333317 | Name: Protoporphyrin IX
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Protoporphyrin IX is an organic compound, classified as a porphyrin, that plays an important role in living organisms as a precursor to other critical compounds like heme (hemoglobin) and chlorophyll. It is a deeply colored solid that is not soluble in water. The name is often abbreviated as PPIX. Protoporphyrin IX florescence from 5-ALA administration is used in fluorescent-guided surgery of glioblastoma. Protoporphyrin IX is an important precursor for synthesis of verteporfin, an approved photosensitizer.

Chemical Structure

Protoporphyrin IX
Protoporphyrin IX
CAS#553-12-8

Theoretical Analysis

MedKoo Cat#: 333317

Name: Protoporphyrin IX

CAS#: 553-12-8

Chemical Formula: C34H34N4O4

Exact Mass: 562.2580

Molecular Weight: 562.67

Elemental Analysis: C, 72.58; H, 6.09; N, 9.96; O, 11.37

Price and Availability

Size Price Availability Quantity
1g USD 450.00 2 Weeks
2g USD 750.00 2 Weeks
5g USD 1,650.00 2 Weeks
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Related CAS #
No Data
Synonym
Protoporphyrin IX; Kammerer’s porphyrin; NSC 177389; NSC 2632; Ooporphyrin; Protoporphyrin;
IUPAC/Chemical Name
3,3'-(3,8,13,17-tetramethyl-7,12-divinylporphyrin-2,18-diyl)dipropionic acid
InChi Key
KSFOVUSSGSKXFI-UJJXFSCMSA-N
InChi Code
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 Code
O=C(O)CCC=1C=2N=C(C=C3NC(=CC4=NC(=CC=5NC(C2)=C(C5C)CCC(=O)O)C(C=C)=C4C)C(C=C)=C3C)C1C
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
Protoporphyrin IX is soluble in polar organic solvents, especially pyridine. Dissolve initially in 0.1M base (Tris base or NaOH). Add a water miscible organic solvent (EtOH, MeOH, DMSO, DMF) until the solution is 50/50 base/solvent. When a clear solution is obtained, it can be diluted into an aqueous medium and titrated or buffered to any pH >7. Use immediately. Protoporphyrin IX slowly degrades in solution.
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
The compound is encountered in nature in the form of complexes where the two inner hydrogen atoms are replaced by a divalent metal cation. When complexed with an iron(II) (ferrous) cation Fe2+, the molecule is called heme. Hemes are prosthetic groups in some important proteins. These heme-containing proteins include hemoglobin, myoglobin, and cytochrome c. Complexes can also be formed with other metal ions, such as zinc. Protoporphyrin IX is active as a photosensitizer and is a component of nitric oxide synthase for NOS generation. Protoporphyrin IX is a substrate for heme oxygenases affording cellular protection and producing biliverdin and CO, a secondary messenger in cells, and metallated (Fe) versions of heme are one of the most abundant and widely used metalloporphyrins in the biosphere. Metallated protoporphyrin derivatives especially those containing tin and first row transition metals such as Zn, Mn, Cr, Ni are extensively used as experimental heme oxygenase inhibitors. Frontier Specialty Chemicals produces a wide range of metallated protoporphyrin derivatives for your experimental needs , including 54Fe and 57Fe protoporphyrin chlorides Gallium (III) protoporphyrin derivatives display potent photodynamic antimicrobial effects and is of current interest for the treatment of antibiotic resistant infections. Electrocatalytic reduction of CO2 to formic acid was demonstrated for various metallated protoporphyrins. Cobalt (III) protoporphyrin, when inserted into myoglobin serves as a catalyst for the reduction of N2O to N2. Co(III) and Sn(IV) protoporphyrin derivatives inactivate arboviruses including Chikungunya and Zika by targeting the viral envelope. Protoporphyrin is a potential biomarker for cancer screening. Aggregation behavior of protoporphyrin in water is complex and is dependent on pH and ionic strength. Magnesium (II) Protoporphyrin is the first intermediate in the biosynthesis of chlorophylls from protoporphyrin IX. Zinc (II) protoporphyrin IX is a potent competitive inhibitor of heme oxygenase and is formed naturally in the case of iron deficiency of lead poisoning. Copper (II) protoporphyrin IX does not inhibit heme oxygenase and is used as a negative control in inhibition studies. N-methyl protoporphyrin IX is a transition state analogue and a potent inhibitor of ferrochelatase, the enzyme that inserts iron into protoporphyrin IX and is commonly used to induce haem deficiency in cell cultures. Protoporphyrin is a reactive molecule and readily reacts with electrophilic reagents at the vinyl groups to produce new derivatives and is often an undesirable reaction pathway that is involved in its degradation in solution. Mesoporphyrin IX is very similar to protoporphyrin IX and is more stable for catalytic and material science applications that do not require the beta-vinyl groups.

Preparing Stock Solutions

The following data is based on the product molecular weight 562.67 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Xu L, Qi Q, Zhu J, Ma X. N-Methyl Protoporphyrin IX: An Understudied Porphyrin. Chem Res Toxicol. 2022 Dec 19;35(12):2186-2193. doi: 10.1021/acs.chemrestox.2c00214. Epub 2022 Dec 2. PMID: 36459538; PMCID: PMC10039788. 2: Hussain Z, Qi Q, Zhu J, Anderson KE, Ma X. Protoporphyrin IX-induced phototoxicity: Mechanisms and therapeutics. Pharmacol Ther. 2023 Aug;248:108487. doi: 10.1016/j.pharmthera.2023.108487. Epub 2023 Jun 29. PMID: 37392940; PMCID: PMC10529234. 3: Courrol LC, de Oliveira Silva FR, Masilamani V. SARS-CoV-2, hemoglobin and protoporphyrin IX: Interactions and perspectives. Photodiagnosis Photodyn Ther. 2021 Jun;34:102324. doi: 10.1016/j.pdpdt.2021.102324. Epub 2021 May 15. PMID: 33965601; PMCID: PMC8123386. 4: Dibona-Villanueva L, Fuentealba D. Protoporphyrin IX-Chitosan Oligosaccharide Conjugate with Potent Antifungal Photodynamic Activity. J Agric Food Chem. 2022 Aug 3;70(30):9276-9282. doi: 10.1021/acs.jafc.2c01644. Epub 2022 Jul 22. PMID: 35866700. 5: Bernardo-Seisdedos G, Schedlbauer A, Pereira-Ortuzar T, Mato JM, Millet O. Protoporphyrin IX Binds to Iron(II)-Loaded and to Zinc-Loaded Human Frataxin. Life (Basel). 2023 Jan 12;13(1):222. doi: 10.3390/life13010222. PMID: 36676171; PMCID: PMC9866752. 6: Nasir-Moin M, Wadiura LI, Sacalean V, Juros D, Movahed-Ezazi M, Lock EK, Smith A, Lee M, Weiss H, Müther M, Alber D, Ratna S, Fang C, Suero-Molina E, Hellwig S, Stummer W, Rössler K, Hainfellner JA, Widhalm G, Kiesel B, Reichert D, Mischkulnig M, Jain R, Straehle J, Neidert N, Schnell O, Beck J, Trautman J, Pastore S, Pacione D, Placantonakis D, Oermann EK, Golfinos JG, Hollon TC, Snuderl M, Freudiger CW, Heiland DH, Orringer DA. Localization of protoporphyrin IX during glioma-resection surgery via paired stimulated Raman histology and fluorescence microscopy. Nat Biomed Eng. 2024 Jun;8(6):672-688. doi: 10.1038/s41551-024-01217-3. Epub 2024 Jul 10. PMID: 38987630. 7: Pétusseau A, Bruza P, Pogue B. Protoporphyrin IX delayed fluorescence imaging: a modality for hypoxia-based surgical guidance. J Biomed Opt. 2022 Oct;27(10):106005. doi: 10.1117/1.JBO.27.10.106005. PMID: 36217225; PMCID: PMC9549807. 8: Gibbard JA , Clarke CJ , Verlet JRR . Photoelectron spectroscopy of the protoporphyrin IX dianion. Phys Chem Chem Phys. 2021 Sep 14;23(34):18425-18431. doi: 10.1039/d1cp03075b. Epub 2021 Aug 23. PMID: 34612383. 9: Feizi S, Awad M, Nepal R, Cooksley CM, Psaltis AJ, Wormald PJ, Vreugde S. Deferiprone-gallium-protoporphyrin (IX): A promising treatment modality against Mycobacterium abscessus. Tuberculosis (Edinb). 2023 Sep;142:102390. doi: 10.1016/j.tube.2023.102390. Epub 2023 Jul 24. PMID: 37506532. 10: Hennig G, Gruber C, Vogeser M, Stepp H, Dittmar S, Sroka R, Brittenham GM. Dual-wavelength excitation for fluorescence-based quantification of zinc protoporphyrin IX and protoporphyrin IX in whole blood. J Biophotonics. 2014 Jul;7(7):514-24. doi: 10.1002/jbio.201200228. Epub 2013 Mar 1. PMID: 23450826. 11: Choi KR, Yu HE, Lee SY. Production of zinc protoporphyrin IX by metabolically engineered Escherichia coli. Biotechnol Bioeng. 2022 Nov;119(11):3319-3325. doi: 10.1002/bit.28195. Epub 2022 Aug 4. PMID: 35882952. 12: Kiening M, Lange N. A Recap of Heme Metabolism towards Understanding Protoporphyrin IX Selectivity in Cancer Cells. Int J Mol Sci. 2022 Jul 19;23(14):7974. doi: 10.3390/ijms23147974. PMID: 35887311; PMCID: PMC9324066. 13: Willows RD. Biosynthesis of chlorophylls from protoporphyrin IX. Nat Prod Rep. 2003 Jun;20(3):327-41. doi: 10.1039/b110549n. PMID: 12828371. 14: Fontana LC, Pinto JG, Vitorio GDS, Ferreira I, Pacheco-Soares C, Mamone LA, Strixino JF. Photodynamic effect of protoporphyrin IX in gliosarcoma 9l/lacZ cell line. Photodiagnosis Photodyn Ther. 2022 Mar;37:102669. doi: 10.1016/j.pdpdt.2021.102669. Epub 2021 Dec 2. PMID: 34863947. 15: Cui Y, Zhang L, Liu J, Zhang T, Sugahara A, Momotake A, Yamamoto Y, Mao ZW, Tai H. Hydrogen Evolution of a Unique DNAzyme Composed of Cobalt-Protoporphyrin IX and G-Quadruplex DNA. ChemSusChem. 2024 Jan 8;17(1):e202301244. doi: 10.1002/cssc.202301244. Epub 2023 Oct 27. PMID: 37681481. 16: Zhang C, Ma C, Zhu L, Yao M. Simultaneous determination of protoporphyrin IX and magnesium protoporphyrin IX in Arabidopsis thaliana and Camellia sinensis using UPLC-MS/MS. Plant Methods. 2023 Mar 30;19(1):34. doi: 10.1186/s13007-023-01008-y. PMID: 36998023; PMCID: PMC10061815. 17: Wang B, Xu YT, Zhang L, Zheng J, Sroka R, Wang HW, Wang XL. Protoporphyrin IX fluorescence as potential indicator of psoriasis severity and progression. Photodiagnosis Photodyn Ther. 2017 Sep;19:304-307. doi: 10.1016/j.pdpdt.2017.05.016. Epub 2017 Jun 15. PMID: 28625924. 18: Shan L. Protoporphyrin IX and IR-820 fluorophore–encapsulated organically modified silica nanoparticles. 2012 Jun 29 [updated 2012 Aug 7]. In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004–2013. PMID: 22896867. 19: Desgranges S, Juzenas P, Vasovic V, Gederaas OA, Lindgren M, Warloe T, Peng Q, Contino-Pépin C. Amphiphilic Protoporphyrin IX Derivatives as New Photosensitizing Agents for the Improvement of Photodynamic Therapy. Biomedicines. 2022 Feb 10;10(2):423. doi: 10.3390/biomedicines10020423. PMID: 35203632; PMCID: PMC8962274.

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