创建日期
2005-11-16 15:48:42 UTC
更新日期
2020-04-23 20:56:37 UTC
描述
Protoporphyrins are tetrapyrroles containing 4 methyl, 2 propionic, and 2 vinyl side chains. Protoporphyrin is produced by oxidation of the methylene bridge of protoporphyrinogen. Protoporphyrin IX is the only naturally occurring isomer; it is an intermediate in heme biosynthesis, combining with ferrous iron to form protoheme IX, the heme prosthetic group of hemoglobin. Protoporphyrin IX is created by the enzyme protoporphyrinogen oxidase. The enzyme ferrochelatase converts it into heme. Protoporphyrin IX naturally occurs in small amounts in feces. Protoporphyrin IX is also responsible for the brown pigment (ooporphyrin) of birds' eggs. Protoporphyrin IX is used as a branch point in the biosynthetic pathway leading to heme (by insertion of iron) and chlorophylls (by insertion of Mg and further side-chain transformation). Protoporphyrin IX can be used to treat liver disorders, mainly as the sodium salt. Under certain conditions, protoporphyrin IX can act as a neurotoxin, a phototoxin, and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. A phototoxin causes cell damage upon exposure to light. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of porphyrins are associated with porphyrias such as porphyria variegate, acute intermittent porphyria, and hereditary coproporphyria (HCP). In particular, it is accumulated and excreted excessively in the feces in acute intermittent porphyria, protoporphyria, and variegate porphyria. There are several types of porphyrias (most are inherited). Hepatic porphyrias are characterized by acute neurological attacks (seizures, psychosis, extreme back and abdominal pain, and an acute polyneuropathy), while the erythropoietic forms present with skin problems (usually a light-sensitive blistering rash and increased hair growth). The neurotoxicity of porphyrins may be due to their selective interactions with tubulin, which disrupt microtubule formation and cause neural malformations (PMID: 3441503).
同义词
1:3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid
2:3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoic acid
3:H2PpIX
4:Kammerer's prophyrin
5:Ooporphyrin
6:Porphyrinogen IX
7:3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionate
8:3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoate
9:3,3'-(3,7,12,17-Tetramethyl-8,13-divinylporphine-2,18-diyl)di
10:PpIX
11:Protoporphyrin
12:Protoporphyrin-"ix"
13:Protoporphyrin-IX
化学名称
3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid
传统名称
3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid
代谢物结构字符串
CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O
inchi标识符
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-
印记键
KSFOVUSSGSKXFI-UJJXFSCMSA-N
分类学
description: belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.
description:Porphyrins
kingdom:Organic compounds
super_class:Organoheterocyclic compounds
class:Tetrapyrroles and derivatives
sub_class:Porphyrins
molecular_framework:
本体论
term:Physiological effect
definition:The effect on an organism physiology, resulting from its exposure to a chemical.
parent_id:
level:1
type:parent
term:Health effect
definition:A health condition or observation associated with a stimuli or with a biological activity of a chemical.
parent_id:7693
*level:2
type:parent
term:Health condition
definition:A health effect that consists on short or long-term disease, condition, disorder, syndrome or constant abnormality.
parent_id:7694
**level:3
type:parent
term:Porphyria
definition:An inherited metabolic disorder that involves certain enzymes in the heme bio-synthetic pathway resulting in the overproduction and accumulation of the porphyrins. (do).
parent_id:7695
***level:4
type:child
term:Hereditary coproporphyria
definition:
parent_id:7695
***level:4
type:child
synonym:Hcp
term:Disposition
definition:A concept that describes the origin of a chemical, its location within an organism, or its route of exposure.
parent_id:
level:1
type:parent
term:Route of exposure
definition:A mean by which a chemical agent comes in contact with an organism, either under intended or unintended circumstances.
parent_id:7724
*level:2
type:parent
term:Enteral
definition:Chemical exposure via the alimentary canal (mouth to anus).
parent_id:7743
**level:3
type:parent
term:Ingestion
definition:Chemical exposure facilitated by entry through the mouth.
parent_id:7744
***level:4
type:child
synonym:Digestion
term:Source
definition:Natural or synthetic origin of a chemical.
parent_id:7724
*level:2
type:parent
term:Endogenous
definition:
parent_id:7735
**level:3
type:child
term:Food
definition:
parent_id:7735
**level:3
type:child
term:Biological
definition:A living organism (species or a higher taxonomy rank), in which a chemical can be found.
parent_id:7735
**level:3
type:parent
term:Plant
definition:A living organism belonging to the kingdom plantea. typically, it grows in a permanent site, absorbs water and inorganic substances through its roots, and synthesizes nutrients in its leaves by photosynthesis using the green pigment chlorophyll. examples incude trees, shrubs, herbs, grasses, ferns, and mosses.
parent_id:7736
***level:4
type:child
synonym:Flora
term:Biological location
definition:The physiological origin within an organism, including anatomical compnents, biofluids and excreta.
parent_id:7724
*level:2
type:parent
term:Cell and elements
definition:An anatomical organizational level comprising of a single cell (or a fragment in some exceptions). a cell is defined by its type or function. it is the smallest unit of living structure capable of independent existence, composed of a membrane-enclosed mass of protoplasm and containing a nucleus or nucleoid.
parent_id:7725
**level:3
type:parent
term:Cell
definition:
parent_id:7732
***level:4
type:parent
term:Element
definition:
parent_id:7732
***level:4
type:parent
term:Tissue and substructures
definition:An anatomical organizational level including multiple cells yet not comprising a complete organ .
parent_id:7725
**level:3
type:parent
term:Adipose tissue
definition:A specialized form of connective tissue consisting primarily of adipocytes (fat cells), surrounded by a meshwork of collagen fibers. (NCI)
parent_id:7729
***level:4
type:child
synonym:Fat tissue
synonym:Body fat
synonym:Adipose
term:Epidermis
definition:The epithelial portion of the skin (cutis). it consists of the following layers: stratum corneum (horny layer), stratum granulosum (granular layer), stratum spinosum (prickle cell layer), and stratum basale (basal cell layer). (nci).
parent_id:7729
***level:4
type:child
term:Organ and components
definition:An anatomical organizational level including multiple tissues or substructures, which enables a common biological function.
parent_id:7725
**level:3
type:parent
term:Intestine
definition:The portion of the gastrointestinal tract that includes the small and large intestines.
parent_id:7727
***level:4
type:child
term:Testicle
definition:Either of the paired male reproductive glands that produce the male germ cells and the male hormones. (nci).
parent_id:7727
***level:4
type:child
synonym:Testes
synonym:Testis
term:Spleen
definition:An abdominal organ that is part of the hematopoietic and immune systems. it is composed of the white pulp and the red pulp and is surrounded by a capsule. (nci).
parent_id:7727
***level:4
type:child
term:Bladder
definition:The distensible sac-like organ that functions as a reservoir of urine, collecting from the kidneys and eliminating via the urethra. (nci).
parent_id:7727
***level:4
type:child
term:Liver
definition:An abdominal organ that has variable lobation which are composed mainly of hepatic lobules. (nci).
parent_id:7727
***level:4
type:child
term:Skin
definition:An organ that constitutes the external surface of the body. it consists of the epidermis, dermis, and skin appendages. (nci).
parent_id:7727
***level:4
type:child
term:Kidney
definition:The organs of the urinary tract located in the retroperitoneal cavity adjacent to the spine and composed of the renal cortex and the renal medulla. (nci).
parent_id:7727
***level:4
type:child
synonym:Kidneys
term:Endocrine gland
definition:
parent_id:7727
***level:4
type:parent
term:Biofluid and excreta
definition:A liquid, semi-solid or solid material originating in the body.
parent_id:7725
**level:3
type:parent
term:Blood
definition:A liquid tissue with the primary function of transporting oxygen and carbon dioxide (nci). it supplies the tissues with nutrients, removes waste products, and contains various components of the immune system defending the body against infection.
parent_id:7731
***level:4
type:child
term:Subcellular
definition:An anatomical organizational level including a component within a biological cell .
parent_id:7725
**level:3
type:parent
term:Cytoplasm
definition:The portion of the cell contained within the plasma membrane but excluding the nucleus.
parent_id:7730
***level:4
type:child
synonym:Cytoplasma
term:Membrane
definition:
parent_id:7730
***level:4
type:child
term:Mitochondria
definition:
parent_id:7730
***level:4
type:child
term:Cell membrane
definition:A cellular compartment that separates a cellВ interiorВ from its exterior.
parent_id:7730
***level:4
type:child
synonym:Cellular membrane
term:Process
definition:Biological or chemical events, or a series thereof, leading to a known function or end-product.
parent_id:
level:1
type:parent
term:Naturally occurring process
definition:Naturally-occurring molecular events or a series thereof, leading to a known function or end-product.
parent_id:7659
*level:2
type:parent
term:Biological process
definition:Biological or chemical events or a series thereof, leading to a known function or end-product within an organism.
parent_id:7660
**level:3
type:parent
term:Biochemical pathway
definition:A linked series of chemical reactions that occur in a defined order within or between organism cells, and lead to a known function or end product.
parent_id:7661
***level:4
type:parent
term:Role
definition:The purpose or function assumed by a chemical, either naturally or as intended by humans .
parent_id:
level:1
type:parent
term:Indirect biological role
definition:An indirect function of a chemical which affect the physiological state of any organism (apart from the source organism, if of biological source).
parent_id:7671
*level:2
type:parent
term:Neurotoxin
definition:A chemical substance that interferes with the normal functioning of the nervous system.
parent_id:7691
**level:3
type:child
synonym:Neurotoxic
synonym:Neurotoxic agent
term:Phototoxin
definition:A chemical substance that leads to cell damage upon exposure to light.
parent_id:7691
**level:3
type:child
term:Metabotoxin
definition:An endogenous metabolite that causes adverse health effects at chronically high levels.
parent_id:7691
**level:3
type:child
term:Biological role
definition:The biological function of a chemical. the biological role answers the question how a chemical is involved in molecular processes in an organism. this can include biochemical effects of non-endogenous chemicals, which are also assigned an industrial application such as pharmaceuticals. the biological role is limited to cellular levls, and will not include role at system process level, such as a chemical which has a role in a disease.
parent_id:7671
*level:2
type:parent
term:Metabolite
definition:A chemical substance produced during metabolism process, as an intermediate or end-product.
parent_id:7672
**level:3
type:child
term:Industrial application
definition:The assumed function of a chemical utilized by human.
parent_id:7671
*level:2
type:parent
term:Pharmaceutical industry
definition:A pharmacologic activity for which a chemical substance is utilized owing to its biological role.
parent_id:7678
**level:3
type:parent
term:Pharmaceutical
definition:
parent_id:7679
***level:4
type:child
term:Photosensitizing agent
definition:A chemical substance that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. (chebi).
parent_id:7679
***level:4
type:child
实验性质
1:
kind:water_solubility
value:0.169 mg/mL at 25 °C
source:
2:
kind:melting_point
value:300 °C
source:
预测性质
1:
kind:logp
value:4.40
source:ALOGPS
2:
kind:logs
value:-4.41
source:ALOGPS
3:
kind:solubility
value:0.022 g/L
source:ALOGPS
4:
kind:logp
value:6.78
source:ChemAxon
5:
kind:pka_strongest_acidic
value:3.68
source:ChemAxon
6:
kind:pka_strongest_basic
value:4.96
source:ChemAxon
7:
kind:iupac
value:3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid
source:ChemAxon
8:
kind:average_mass
value:562.6582
source:ChemAxon
9:
kind:mono_mass
value:562.258005596
source:ChemAxon
10:
kind:smiles
value:CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O
source:ChemAxon
11:
kind:formula
value:C34H34N4O4
source:ChemAxon
12:
kind:inchi
value: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-
source:ChemAxon
13:
kind:inchikey
value:KSFOVUSSGSKXFI-UJJXFSCMSA-N
source:ChemAxon
14:
kind:polar_surface_area
value:131.96
source:ChemAxon
15:
kind:refractivity
value:163.81
source:ChemAxon
16:
kind:polarizability
value:66.03
source:ChemAxon
17:
kind:rotatable_bond_count
value:8
source:ChemAxon
18:
kind:acceptor_count
value:6
source:ChemAxon
19:
kind:donor_count
value:4
source:ChemAxon
20:
kind:physiological_charge
value:-2
source:ChemAxon
21:
kind:formal_charge
value:0
source:ChemAxon
22:
kind:number_of_rings
value:5
source:ChemAxon
23:
kind:bioavailability
value:No
source:ChemAxon
24:
kind:rule_of_five
value:No
source:ChemAxon
25:
kind:ghose_filter
value:No
source:ChemAxon
26:
kind:veber_rule
value:No
source:ChemAxon
27:
kind:mddr_like_rule
value:Yes
source:ChemAxon
生物学性质
1:
cellular:(1):Cytoplasm
cellular:(2):Membrane
cellular:(3):Mitochondria
2:
biospecimen:(1):Blood
3:
tissue:(1):Adipose Tissue
tissue:(2):Adrenal Medulla
tissue:(3):Bladder
tissue:(4):Epidermis
tissue:(5):Erythrocyte
tissue:(6):Fibroblasts
tissue:(7):Intestine
tissue:(8):Kidney
tissue:(9):Leukocyte
tissue:(10):Liver
tissue:(11):Platelet
tissue:(12):Spleen
tissue:(13):Testis
tissue:(14):Thyroid Gland
4:
[1]:
name:Acute Intermittent Porphyria
smpdb_id:SMP00344
kegg_map_id:
[2]:
name:Congenital Erythropoietic Porphyria (CEP) or Gunther Disease
smpdb_id:SMP00345
kegg_map_id:
[3]:
name:Hereditary Coproporphyria (HCP)
smpdb_id:SMP00342
kegg_map_id:
[4]:
name:Porphyria Variegata (PV)
smpdb_id:SMP00346
kegg_map_id:
[5]:
name:Porphyrin Metabolism
smpdb_id:SMP00024
kegg_map_id:map00860
正常浓度
1:
biospecimen:Blood
concentration_value:0.66 +/- 0.18
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
2:
biospecimen:Blood
concentration_value:0.53 +/- 0.13
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Male
subject_condition:Normal
3:
biospecimen:Blood
concentration_value:1.09 +/- 0.57
concentration_units:uM
subject_age:Newborn (0-30 days old)
subject_sex:Both
subject_condition:Normal
异常浓度
1:
biospecimen:Blood
concentration_value:0-1.244
concentration_units:uM
patient_age:Adult (>18 years old)
patient_sex:Male
patient_information:Protoporphyria, Erythropoietic
疾病参考
1:
name:Protoporphyria, Erythropoietic
omim_id:177000
[1]:
reference_text:MAGNUS IA, JARRETT A, PRANKERD TA, RIMINGTON C: Erythropoietic protoporphyria. A new porphyria syndrome with solar urticaria due to protoporphyrinaemia. Lancet. 1961 Aug 26;2(7200):448-51.
pubmed_id:13765301
代谢途径的数据库编号
PROTOPORPHYRIN_IX
综合参考
Games, David E.; Jackson, Anthony H.; Jackson, J. Richard; Belcher, Roderick V.; Smith, Sydney G. Biosynthesis of protoporphyrin-IX from coproporphyrinogen-III. Journal of the Chemical Society, Chemical Communications (1976), (6), 187-8.
一般参考
1:
protein_accession:HMDBP00251
name:Coproporphyrinogen-III oxidase, mitochondrial
uniprot_id:P36551
gene_name:CPOX
protein_type:Unknown
2:
protein_accession:HMDBP01021
name:Protoporphyrinogen oxidase
uniprot_id:P50336
gene_name:PPOX
protein_type:Unknown
3:
protein_accession:HMDBP01058
name:Ferrochelatase, mitochondrial
uniprot_id:P22830
gene_name:FECH
protein_type:Unknown
4:
protein_accession:HMDBP02077
name:Ferritin light chain
uniprot_id:P02792
gene_name:FTL
protein_type:Unknown
5:
protein_accession:HMDBP09176
name:Ferrochelatase
uniprot_id:Q53FU1
gene_name:
protein_type:Enzyme
6:
protein_accession:HMDBP09179
name:Ferrochelatase
uniprot_id:Q5TZY0
gene_name:
protein_type:Enzyme
7:
protein_accession:HMDBP09180
name:Ferrochelatase
uniprot_id:Q7KZA3
gene_name:DKFZp686P18130
protein_type:Enzyme
蛋白质结合
1:
reference_text:Messmann H, Knuchel R, Baumler W, Holstege A, Scholmerich J: Endoscopic fluorescence detection of dysplasia in patients with Barrett's esophagus, ulcerative colitis, or adenomatous polyps after 5-aminolevulinic acid-induced protoporphyrin IX sensitization. Gastrointest Endosc. 1999 Jan;49(1):97-101.
pubmed_id:9869731
2:
reference_text:Stankiewicz A, Lutz W, Krajewska B, Szulc B: [Plasma indicators of iron metabolism in persons occupationally exposed to organic solvents with normal and increased levels of protoporphyrin IX in erythrocytes]. Pol Tyg Lek. 1986 Jul 7;41(27):851-4.
pubmed_id:3763462
3:
reference_text:Stankiewicz A: [Erythrocyte protoporphyrin IX in occupational exposure to asbestos]. Med Pr. 1984;35(5):351-4.
pubmed_id:6530952
4:
reference_text:Sudworth CD, Stringer MR, Cruse-Sawyer JE, Brown SB: Fluorescence microspectroscopy technique for the study of intracellular protoporphyrin IX dynamics. Appl Spectrosc. 2003 Jun;57(6):682-8.
pubmed_id:14658702
5:
reference_text:Kufner G, Schlegel H, Jager R: A spectrophotometric micromethod for determining erythrocyte protoporphyrin-IX in whole blood or erythrocytes. Clin Chem Lab Med. 2005;43(2):183-91.
pubmed_id:15843214
6:
reference_text:Stankiewicz A: The concentration of protoporphyrin IX in workers occupationally exposed to lead. Mater Med Pol. 1989 Apr-Jun;21(2):100-2.
pubmed_id:2488459
7:
reference_text:Krieg RC, Fickweiler S, Wolfbeis OS, Knuechel R: Cell-type specific protoporphyrin IX metabolism in human bladder cancer in vitro. Photochem Photobiol. 2000 Aug;72(2):226-33.
pubmed_id:10946577
8:
reference_text:Bailey GG, Needham LL: Simultaneous quantification of erythrocyte zinc protoporphyrin and protoporphyrin IX by liquid chromatography. Clin Chem. 1986 Dec;32(12):2137-42.
pubmed_id:3779978
9:
reference_text:Chisolm J Jr, Brown DH: Micro-scale photofluorometric determination of "free erythrocyte pophyrin" (protoporphyrin IX). Clin Chem. 1975 Oct;21(11):1669-82.
pubmed_id:1164799
10:
reference_text:Casas A, Batlle AM, Butler AR, Robertson D, Brown EH, MacRobert A, Riley PA: Comparative effect of ALA derivatives on protoporphyrin IX production in human and rat skin organ cultures. Br J Cancer. 1999 Jul;80(10):1525-32.
pubmed_id:10408393
11:
reference_text:Smits T, Robles CA, van Erp PE, van de Kerkhof PC, Gerritsen MJ: Correlation between macroscopic fluorescence and protoporphyrin IX content in psoriasis and actinic keratosis following application of aminolevulinic acid. J Invest Dermatol. 2005 Oct;125(4):833-9.
pubmed_id:16185285
12:
reference_text:Bartosova J, Hrkal Z: Accumulation of protoporphyrin-IX (PpIX) in leukemic cell lines following induction by 5-aminolevulinic acid (ALA). Comp Biochem Physiol C Toxicol Pharmacol. 2000 Jul;126(3):245-52.
pubmed_id:11048674
13:
reference_text:Sakai T, Takeuchi Y, Ikeya Y, Araki T, Ushio K: [Automated HPLC method for determining zinc protoporphyrin IX and protoporphyrin IX in erythrocytes of workers exposed to lead]. Sangyo Igaku. 1988 Nov;30(6):467-74.
pubmed_id:3221502
14:
reference_text:Stankiewicz A, Lutz W, Szeszko A: [Protoporphyrin IX level in erythrocytes of persons with alcoholic liver cirrhosis]. Pol Tyg Lek. 1985 Jul 15;40(28):787-9.
pubmed_id:4059100
15:
reference_text:Star WM, Aalders MC, Sac A, Sterenborg HJ: Quantitative model calculation of the time-dependent protoporphyrin IX concentration in normal human epidermis after delivery of ALA by passive topical application or lontophoresis. Photochem Photobiol. 2002 Apr;75(4):424-32.
pubmed_id:12003134
16:
reference_text:von Beckerath M, Juzenas P, Ma LW, Iani V, Lofgren L, Moan J: The influence of UV exposure on 5-aminolevulinic acid-induced protoporphyrin IX production in skin. Photochem Photobiol. 2001 Dec;74(6):825-8.
pubmed_id:11783939
17:
reference_text:Gottsch JD, Graham CR Jr, Hairston RJ, Chen CH, Green WR, Stark WJ: Protoporphyrin IX photosensitization of corneal endothelium. Arch Ophthalmol. 1989 Oct;107(10):1497-500.
pubmed_id:2803100
18:
reference_text:Bissonnette R, Zeng H, McLean DI, Korbelik M, Lui H: Oral aminolevulinic acid induces protoporphyrin IX fluorescence in psoriatic plaques and peripheral blood cells. Photochem Photobiol. 2001 Aug;74(2):339-45.
pubmed_id:11547574
19:
reference_text:Rick K, Sroka R, Stepp H, Kriegmair M, Huber RM, Jacob K, Baumgartner R: Pharmacokinetics of 5-aminolevulinic acid-induced protoporphyrin IX in skin and blood. J Photochem Photobiol B. 1997 Oct;40(3):313-9.
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