protoporphyrin (CHEBI:15430)

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CHEBI:15430 - protoporphyrin

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ChEBI Name	protoporphyrin

ChEBI ID	CHEBI:15430

Definition	A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyrins.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:14961, CHEBI:14959, CHEBI:14960, CHEBI:26358, CHEBI:8592

Supplier Information	eMolecules:531182, eMolecules:18593072

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Molfile

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reading 76 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

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76 atoms created

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Wikipedia	License
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 contains a porphine core, a tetrapyrrole macrocycle with a marked aromatic character. Protoporphyrin IX is essentially planar, except for the N-H bonds that are bent out of the plane of the rings, in opposite (trans) directions.
Read full article at Wikipedia

Formula

C34H34N4O4

Net Charge

Average Mass

562.65832

Monoisotopic Mass

562.25801

InChI

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-

InChIKey

KSFOVUSSGSKXFI-UJJXFSCMSA-N

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

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. cofactor An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group). (via porphyrins )

Application(s):	photosensitizing agent A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	protoporphyrin (CHEBI:15430) has role Escherichia coli metabolite (CHEBI:76971) protoporphyrin (CHEBI:15430) has role metabolite (CHEBI:25212) protoporphyrin (CHEBI:15430) has role mouse metabolite (CHEBI:75771) protoporphyrin (CHEBI:15430) has role photosensitizing agent (CHEBI:47868) protoporphyrin (CHEBI:15430) is a protoporphyrins (CHEBI:26361) protoporphyrin (CHEBI:15430) is conjugate acid of protoporphyrin(2−) (CHEBI:57306) protoporphyrin (CHEBI:15430) is conjugate acid of protoporphyrinate (CHEBI:36159)

Incoming	hematoporphyrin (CHEBI:36162) has functional parent protoporphyrin (CHEBI:15430) protoporphyrin monomethyl ester (CHEBI:36160) has functional parent protoporphyrin (CHEBI:15430) protoporphyrin(2−) (CHEBI:57306) is conjugate base of protoporphyrin (CHEBI:15430) protoporphyrinate (CHEBI:36159) is conjugate base of protoporphyrin (CHEBI:15430)

IUPAC Name

7,12-diethenyl-3,8,13,17-tetramethylporphyrin-2,18-dipropanoic acid

Synonyms	Sources
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid	HMDB
3,7,12,17-tetramethyl-8,13-divinylporphyrin-2,18-dipropanoic acid	IUPAC
H₂ppIX	IUPAC
Kammerer's prophyrin	NIST Chemistry WebBook
ooporphyrin	ChemIDplus
Porphyrinogen IX	KEGG COMPOUND
Protoporphyrin	KEGG COMPOUND
Protoporphyrin IX	KEGG COMPOUND
PROTOPORPHYRIN IX	PDBeChem

Manual Xrefs	Databases
3500	DrugCentral
C00007370	KNApSAcK
C02191	KEGG COMPOUND
DB02285	DrugBank
HMDB0000241	HMDB
PP9	PDBeChem
Protoporphyrin_IX	Wikipedia
PROTOPORPHYRIN_IX	MetaCyc
View more database links

Registry Numbers	Types	Sources
251232	Gmelin Registry Number	Gmelin
380795	Reaxys Registry Number	Reaxys
553-12-8	CAS Registry Number	KEGG COMPOUND
553-12-8	CAS Registry Number	ChemIDplus
553-12-8	CAS Registry Number	NIST Chemistry WebBook
635160	Beilstein Registry Number	Beilstein
635161	Beilstein Registry Number	Beilstein

Citations

Johansson A, Faber F, Kniebühler G, Stepp H, Sroka R, Egensperger R, Beyer W, Kreth FW (2013)
Protoporphyrin IX fluorescence and photobleaching during interstitial photodynamic therapy of malignant gliomas for early treatment prognosis.
Lasers in surgery and medicine 45, 225-234 [PubMed:23533060]
[show Abstract]

Background and objective

Interstitial photodynamic therapy (iPDT) of non-resectable recurrent glioblastoma using 5-aminolevulinic acid (ALA)-induced protoporphyrin IX (PpIX) has shown a promising outcome. It remained unclear, however, to what extent inter- and intra-tumoural differences of PpIX concentrations influence the efficacy of iPDT. In the current pilot study, we analysed PpIX concentrations quantitatively and assessed PpIX induced fluorescence and photobleaching intraoperatively.

Materials and methods

Five patients harbouring non-resectable glioblastomas were included. ALA (20 or 30 mg/kg body weight) was given 5-8 hours before treatment. Stereotactic biopsies were taken throughout the tumour volume for both histological analysis and determination of PpIX concentrations, which were measured by chemical extraction. Cylindrical light diffusors were stereotactically implanted. Prior to and after irradiation, fluorescence measurements were performed. Outcome measurement was based on clinical and neuro-radiological follow up.

Results

In three patients, a strong PpIX fluorescence was seen before treatment, which was completely photobleached after iPDT. High concentrations of PpIX could be detected in viable tumour parts of these patients (mean PpIX uptake per tumour: 1.4-3.0 µM). In the other two patients, however, no or only low PpIX uptake (0-0.6 µM) could be detected. The patients with strong PpIX uptake showed treatment response and long-term clinical stabilisation (no progression in 29, 30 and 36 months), early treatment failure was seen in the remaining two patients (death after 3 and 9 months).

Conclusions

Intra-tumoural PpIX concentrations exhibited pronounced inter- and intra-tumoural variations in glioblastoma, which are directly linked to variable degrees of fluorescence intensity. High intra-tumoural PpIX concentrations with strong fluorescence intensity and complete photobleaching after iPDT seem to be associated with favourable outcome. Real-time monitoring of PpIX fluorescence intensity and photobleaching turned out to be feasible and safe and might be employed for early treatment prognosis of iPDT.

Nakamura T, Saito M, Shimada Y, Fukaya H, Shida Y, Tokuji Y (2011)
Induction of aminolevulinic acid synthase gene expression and enhancement of metabolite, protoporphyrin IX, excretion by organic germanium.
European journal of pharmacology 653, 75-81 [PubMed:21167148]
[show Abstract]

Sznarkowska A, Maleńczyk K, Kadziński L, Bielawski KP, Banecki B, Zawacka-Pankau J (2011)
Targeting of p53 and its homolog p73 by protoporphyrin IX.
FEBS letters 585, 255-260 [PubMed:21146529]
[show Abstract]

Wołuń-Cholewa M, Piedel B (2011)
In vitro photodynamic therapy of cervical cancer.
Ginekologia polska 82, 503-507 [PubMed:21913427]
[show Abstract]

Kim CH, Chung CW, Choi KH, Yoo JJ, Kim DH, Jeong YI, Kang DH (2011)
Effect of 5-aminolevulinic acid-based photodynamic therapy via reactive oxygen species in human cholangiocarcinoma cells.
International journal of nanomedicine 6, 1357-1363 [PubMed:21760730]
[show Abstract]

Ohgari Y, Miyata Y, Chau TT, Kitajima S, Adachi Y, Taketani S (2011)
Quinolone compounds enhance delta-aminolevulinic acid-induced accumulation of protoporphyrin IX and photosensitivity of tumour cells.
Journal of biochemistry 149, 153-160 [PubMed:20961864]
[show Abstract]

Ohgari Y, Miyata Y, Miyagi T, Gotoh S, Ohta T, Kataoka T, Furuyama K, Taketani S (2011)
Roles of porphyrin and iron metabolisms in the δ-aminolevulinic acid (ALA)-induced accumulation of protoporphyrin and photodamage of tumor cells.
Photochemistry and photobiology 87, 1138-1145 [PubMed:21668870]
[show Abstract]

Lyoumi S, Martin-Schmitt C, Touitou Y, Puy H, Djeridane Y (2008)
Melatonin and environmental lighting regulate ALA-S gene expression and So porphyrin biosynthesis in the rat harderian gland.
Chronobiology international 25, 851-867 [PubMed:19005892]
[show Abstract]

Chu ES, Yow CM, Shi M, Ho RJ (2008)
Effects of photoactivated 5-aminolevulinic acid hexyl ester on MDR1 over-expressing human uterine sarcoma cells.
Toxicology letters 181, 7-12 [PubMed:18625294]
[show Abstract]

Last Modified

22 February 2017

ChEBI

CHEBI:15430 - protoporphyrin

Background and objective

Materials and methods

Results

Conclusions

Objectives

Aim

Material and methods

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