coproporphyrins

Summary

Summary: Porphyrins with four methyl and four propionic acid side chains attached to the pyrrole rings. Elevated levels of Coproporphyrin III in the urine and feces are major findings in patients with HEREDITARY COPROPORPHYRIA.

Top Publications

  1. Gross U, Honcamp M, Daume E, Frank M, Düsterberg B, Doss M. Hormonal oral contraceptives, urinary porphyrin excretion and porphyrias. Horm Metab Res. 1995;27:379-83 pubmed
    ..Treatment with the OCs successfully stabilized the latent phase of premenstrual forms of acute hepatic porphyrias. This study demonstrates that low-dose OCs do not affect urinary porphyrin excretion. ..
  2. Moriondo V, Marchini S, Di Gangi P, Ferrari M, Nascimbeni F, Rocchi E, et al. Role of Multidrug-Resistance Protein 2 in coproporphyrin transport: results from experimental studies in bile fistula rat models. Cell Mol Biol (Noisy-le-grand). 2009;55:70-8 pubmed
  3. Nataf R, Skorupka C, Amet L, Lam A, Springbett A, Lathe R. Porphyrinuria in childhood autistic disorder: implications for environmental toxicity. Toxicol Appl Pharmacol. 2006;214:99-108 pubmed
    ..Following DMSA there was a significant (P = 0.002) drop in urinary porphyrin excretion. These data implicate environmental toxicity in childhood autistic disorder. ..
  4. Frank M, Doss M, de Carvalho D. Diagnostic and pathogenetic implications of urinary coproporphyrin excretion in the Dubin-Johnson syndrome. Hepatogastroenterology. 1990;37:147-51 pubmed
    ..an increase in porphobilinogen deaminase (uroporphyrinogen synthase) activity, or 4. a membrane-associated transport disorder with secondary metabolic changes of the isomer pool and enzyme activities. ..
  5. Ahle G, Wierzba S, Haupts M, König M, Gehlen W. Acute left hemispheric syndrome with cortical lesions in a patient with secondary porphyrinuria. J Neurol. 2005;252:983-4 pubmed
  6. Aziz S, Leroy P, Servaes R, Eggermont E, Fevery J. Bilirubin-IXbeta is a marker of meconium, like zinc coproporphyrin. J Pediatr Gastroenterol Nutr. 2001;32:287-92 pubmed
    ..In addition, samples were also submitted to diazo coupling with ethyl anthranilate. Total coproporphyrins and zinc coproporphyrin were assayed for comparison...
  7. Aziz S, Kotal P, Leroy P, Servaes R, Eggermont E, Fevery J. Bilirubin-IXalpha and -IXbeta pigments, coproporphyrins and bile acids in meconium and stools from full-term and preterm neonates during the first month of life. Acta Paediatr. 2001;90:81-7 pubmed
    ..Both zinc coproporphyrin and bilirubin-lXbeta are characteristic compounds of human meconium, diconjugated bilirubin-IXalpha is low or absent in meconium of very preterm infants, and faecal and serum bile acids are high. ..
  8. Borelli C, Merk K, Schaller M, Jacob K, Vogeser M, Weindl G, et al. In vivo porphyrin production by P. acnes in untreated acne patients and its modulation by acne treatment. Acta Derm Venereol. 2006;86:316-9 pubmed
    ..Statistical analysis demonstrated a significant reduction in the porphyrin fractions only in the isotretinoin group which was associated with clinical improvement 2 months after starting therapy. ..
  9. Komagoe K, Tamagake K, Katsu T. The influence of aggregation of porphyrins on the efficiency of photogeneration of hydrogen peroxide in aqueous solution. Chem Pharm Bull (Tokyo). 2006;54:1004-9 pubmed
    ..The present results demonstrated the importance of the state of aggregation of porphyrin to photogenerate H2O2, and the results may help to develop a new type of medicine for photodynamic therapy. ..

More Information

Publications62

  1. Gross U, Frank M, Doss M. Hepatic complications of erythropoietic protoporphyria. Photodermatol Photoimmunol Photomed. 1998;14:52-7 pubmed
    ..In patients with severe cholestatic hepatic failure, liver transplantation is the treatment of choice. ..
  2. Mel nikova YaI -, Kravchuk Z, Preygerzon V, Martsev S. Functional activation of antibodies on modification with Pd(II) coproporphyrin I N-Hydroxysuccinimide ester. Biochemistry (Mosc). 1997;62:924-7 pubmed
  3. Shimizu T, Tawa T, Maruyama T, Oguchi S, Yamashiro Y, Yabuta K. A case of infantile Dubin-Johnson syndrome with high CT attenuation in the liver. Pediatr Radiol. 1997;27:345-7 pubmed
    ..This high attenuation may be a finding specific to infantile DJS and, therefore, abdominal CT may be helpful in the diagnosis. ..
  4. Fretzayas A, Kitsiou S, Papadopoulou A, Nicolaidou P. Clinical expression of co-inherited Dubin-Johnson and thalassaemic heterozygous states. Dig Liver Dis. 2007;39:369-74 pubmed
    ..We report the first family with modified clinical expression of Dubin-Johnson heterozygous state due to genotypic interaction with co-inherited beta and deltabeta thalassaemia, an interaction that has never been described. ..
  5. Takahashi M, Nagao T, Imazeki Y, Matsuzaki K, Minamitani H. Roles of reactive oxygen species in monocyte activation induced by photochemical reactions during photodynamic therapy. Front Med Biol Eng. 2002;11:279-94 pubmed
    ..The result affirms the predominant role of singlet oxygen and superoxide anion radicals in monocyte activation in the VSD effect during PDT. ..
  6. Malina L, Lochman I, Meyer W, Michalikova H. Autoantibodies in sporadic porphyria cutanea tarda. Arch Dermatol Res. 2003;295:109-11 pubmed
    ..The origin of mostly antinuclear antibodies against liver antigens (50, 45 and 56 kDa), detected in seven patients, was not identified and their etiopathogenetic implications remain unknown. ..
  7. Pinelli A, Mussini C, Bertolini B, Buratti M, Trivulzio S. Increased excretion of urine coproporphyrins during daunorubicin administration in patients affected by acute myelogenous leukemia. Pharmacol Res. 2003;48:515-8 pubmed
    ..Erythrocyte and urine porphyrin levels were increased as a result of the leukemic process, but urine coproporphyrins were further increased by daunorubicin treatment...
  8. Carrasco Letelier L, Eguren G, de Mello F, Groves P. Preliminary field study of hepatic porphyrin profiles of Astyanax fasciatus (Teleostei, Characiformes) to define anthropogenic pollution. Chemosphere. 2006;62:1245-52 pubmed
    ..fasciatus is a good bio-indicator of exposure to environmental contaminants, and we propose that this abundant fish species be considered as a sentinel organism for monitoring potential disturbances to freshwater ecosystems. ..
  9. Macours P, Cotton F. Improvement in HPLC separation of porphyrin isomers and application to biochemical diagnosis of porphyrias. Clin Chem Lab Med. 2006;44:1433-40 pubmed
    ..The present RP-HPLC method is specific and efficient for routine analysis of porphyrins in human urine, feces and plasma. ..
  10. O Riordan T, Soini A, Papkovsky D. Monofunctional derivatives of coproporphyrins for phosphorescent labeling of proteins and binding assays. Anal Biochem. 2001;290:366-75 pubmed
    ..Potential applications of these reagents in in vitro diagnostics are discussed. ..
  11. Oberndorfer S, Hitzenberger P, Gruber W, Seidel J, Urbanits S, Doss M, et al. Secondary coproporphyrinuria in a patient with the full clinical picture of a hereditary acute hepatic porphyria. A misleading clinical and biochemical course. J Neurol. 2002;249:1325-6 pubmed
  12. Akgur F, Olguner M. In utero meconium exposure increases spinal cord necrosis in arat model of myelomeningocele. J Pediatr Surg. 2002;37:1384-5; author reply 1383 pubmed
  13. Afonso S, Enriquez De Salamanca R, Batlle A. Photodynamic and light independent action of 8 to 2 carboxylic free porphyrins on some haem-enzymes. Int J Biochem Cell Biol. 2001;33:1208-14 pubmed
    ..On the basis of these results, no correlation between enzyme alterations and the physico-chemical properties of porphyrins could be established. ..
  14. Usta I, Sibai B, Mercer B, Kreamer B, Gourley G. Use of maternal plasma level of zinc-coproporphyrin in the prediction of intrauterine passage of meconium: a pilot study. J Matern Fetal Med. 2000;9:201-3 pubmed
    ..Plasma ZCP might be a promising test for prediction of intrauterine passage of meconium in high-risk patients if confirmed by larger studies. The implications of this prediction on management remain unknown. ..
  15. Tébar M, Aguilera L. [Acute intermittent porphyria and inappropriate ADH syndrome]. Rev Esp Anestesiol Reanim. 2010;57:311-3 pubmed
    ..The diagnosis was confirmed by laboratory findings of elevated d-aminolevulinic acid and porphobilinogen levels and normal stool porphyrins. The patient improved with intravenous hematin infused over 4 days. ..
  16. Wang Q, Ye L, Zhao H, Chen J, Zhou Y. Benchmark dose approach for low-level lead induced haematogenesis inhibition and associations of childhood intelligences with ALAD activity and ALA levels. Sci Total Environ. 2011;409:1806-10 pubmed publisher
    ..It was concluded that blood ALAD activity is a sensitive indicator of early haematological damage due to low-level Pb exposures for children. ..
  17. Benz de Bretagne I, Respaud R, Vourc H P, Halimi J, Caille A, Hulot J, et al. Urinary elimination of coproporphyrins is dependent on ABCC2 polymorphisms and represents a potential biomarker of MRP2 activity in humans. J Biomed Biotechnol. 2011;2011:498757 pubmed publisher
    ..This study provides a proof of concept that UCP I/(I + III) ratio can be used as a biomarker of MRP2 function in clinical studies as it provides quantitative information about the in vivo activity of MRP2 in a given patient. ..
  18. Bannerman R, Garrick L, Rusnak Smalley P, Hoke J, Edwards J. Hemoglobin deficit: an inherited hypochromic anemia in the mouse. Proc Soc Exp Biol Med. 1986;182:52-7 pubmed
  19. Slachtova L, Seda O, Behunova J, Mistrik M, Martasek P. Genetic and biochemical study of dual hereditary jaundice: Dubin-Johnson and Gilbert's syndromes. Haplotyping and founder effect of deletion in ABCC2. Eur J Hum Genet. 2016;24:704-9 pubmed publisher
    ..In this study, we found a novel deletion in ABCC2 gene, described genetic and biochemical features of dual hereditary jaundice and confirmed the existence of founder effect and common haplotype among seven Roma families. ..
  20. Schoenfeld N, Mamet R, Mevasser R, Atsmon A. Experimental latent and acute porphyria in the non-fasted rat; preventive effect of propranolol. Scand J Clin Lab Invest. 1991;51:667-73 pubmed
    ..It is shown that dl-propranolol affects a few parameters in the haem biosynthetic pathway. Its beneficial effect in porphyria is probably the result of increasing the concentration of haem in the free haem pool...
  21. Iida K, Nakamura M, Hanamitsu H, Kajiwara M. Identification of tetrapyrrole compounds excreted by Rhodobacter sphaeroides and sources of the methyl hydrogens of bacteriochlorophyll a biosynthesized by R. sphaeroides, based on 13C-NMR spectral analysis of coproporphyrin III tetramethyl ester. Chem Pharm Bull (Tokyo). 2007;55:1067-9 pubmed
  22. Badiu C, Cristofor D, Voicu D, Coculescu M. Diagnostic traps in porphyria: case report and literature review. Rev Med Chir Soc Med Nat Iasi. 2004;108:584-91 pubmed
    ..The clinician should be aware of the protean manifestations of porphyrias and include them in clinical judgment in various situations. ..
  23. Yang Z, Philips J, Doty R, Giraudi P, Ostrow J, Tiribelli C, et al. Kinetics and specificity of feline leukemia virus subgroup C receptor (FLVCR) export function and its dependence on hemopexin. J Biol Chem. 2010;285:28874-82 pubmed publisher
    ..Together, these data argue that hemopexin has a role in assuring systemic iron balance during homeostasis in addition to its established role as a scavenger during internal bleeding or hemolysis. ..
  24. Heyer N, Echeverria D, Woods J. Disordered porphyrin metabolism: a potential biological marker for autism risk assessment. Autism Res. 2012;5:84-92 pubmed publisher
    ..manifested principally as significantly elevated urinary concentrations of pentacarboxyl (penta) and coproporphyrins, is commonly observed among some children with ASD...
  25. Palma Carlos A, Palma Carlos M. Solar urticaria and porphyrias. Eur Ann Allergy Clin Immunol. 2005;37:17-20 pubmed
    ..Due to the risk of severe forms of disease sometimes drugs induced porphyrias must be considered in all cases of solar urticaria and a correct laboratory study done in the suspected cases. ..
  26. Freesemann A, Bhutani L, Jacob K, Doss M. Interdependence between degree of porphyrin excess and disease severity in congenital erythropoietic porphyria (Günther's disease). Arch Dermatol Res. 1997;289:272-6 pubmed
    ..These findings suggest a close relationship between the metabolic disturbance reflected by porphyrin excess and the severity of disease expression. ..
  27. Yamamoto M, Nagano T, Okura I, Arakane K, Urano Y, Matsumoto K. Production of singlet oxygen on irradiation of a photodynamic therapy agent, zinc-coproporphyrin III, with low host toxicity. Biometals. 2003;16:591-7 pubmed
    ..These results demonstrate the photodynamic generation of 1O2 by Zincphyrin. ..
  28. Wang J, Qi L, Zheng B, Liu F, Moore M, Ng J. Porphyrins as early biomarkers for arsenic exposure in animals and humans. Cell Mol Biol (Noisy-le-grand). 2002;48:835-43 pubmed
    ..Significant alteration in the porphyrin excretion profiles of the younger age (<20 y) arsenic exposed group suggested that porphyrins could be used as early warning biomarkers for chronic exposure to arsenic. ..
  29. Jacob K, Egeler E, Gross U, Doss M. Investigations on the formation of urinary coproporphyrin isomers I-IV in 5-aminolevulinic acid dehydratase deficiency porphyria, acute lead intoxication and after oral 5-aminolevulinic acid loading. Clin Biochem. 1999;32:119-23 pubmed
    ..We analyzed the excretion of total urinary coproporphyrins and the composition of the respective isomers I-IV with ion-pair HPLC methods in these conditions...
  30. Ding Y, Lin B, Huie C. Binding studies of porphyrins to human serum albumin using affinity capillary electrophoresis. Electrophoresis. 2001;22:2210-6 pubmed
  31. Hamblin M, Viveiros J, Yang C, Ahmadi A, Ganz R, Tolkoff M. Helicobacter pylori accumulates photoactive porphyrins and is killed by visible light. Antimicrob Agents Chemother. 2005;49:2822-7 pubmed
    ..Both virulent and drug-resistant strains are killed. The data suggest that phototherapy might be used to treat H. pylori infection in the human stomach. ..
  32. Patwardhan S, Richter C, Vogt A, Blume Peytavi U, Canfield D, Kottner J. Measuring acne using Coproporphyrin III, Protoporphyrin IX, and lesion-specific inflammation: an exploratory study. Arch Dermatol Res. 2017;309:159-167 pubmed publisher
    ..Furthermore, these measurements may be more sensitive and specific in evaluating treatment effects and early signs of acne lesion progression compared to investigators' lesion counts. ..
  33. Yasuma A, Ochiai T, Azuma M, Nishiyama H, Kikuchi K, Kondo M, et al. Exogenous coproporphyrin III production by Corynebacterium aurimucosum and Microbacterium oxydans in erythrasma lesions. J Med Microbiol. 2011;60:1038-42 pubmed publisher
    ..This study supports the view that excess Copro III synthesis by C. aurimucosum and M. oxydans leads to accumulation of porphyrin in cutaneous tissue, which emits a coral-red fluorescence when exposed to Wood's light...
  34. Clavero S, Bishop D, Haskins M, Giger U, Kauppinen R, Desnick R. Feline acute intermittent porphyria: a phenocopy masquerading as an erythropoietic porphyria due to dominant and recessive hydroxymethylbilane synthase mutations. Hum Mol Genet. 2010;19:584-96 pubmed publisher
    ..These animal models may permit further investigation of the pathogenesis of the acute, life-threatening neurological attacks in human AIP and the evaluation of therapeutic strategies. GenBank Accession Numbers: GQ850461-GQ850464. ..
  35. Negroni R, Arechavala A, Maiolo E. [Clinical cases in medical mycology. Case no. 20]. Rev Iberoam Micol. 2006;23:116-8 pubmed
  36. Lee W, Shalita A, Poh Fitzpatrick M. Comparative studies of porphyrin production in Propionibacterium acnes and Propionibacterium granulosum. J Bacteriol. 1978;133:811-5 pubmed
    ..The increased porphyrin production in P. granulosum is apparently associated with increased delta-aminolevulinic acid synthetase activity. ..
  37. Meng J, Gu H, Zheng R, Xing D, Wang J, Wang R, et al. [The non-trauma fluorescence analysis of the porphyrin in the blood of human superficial skin tissue]. Guang Pu Xue Yu Guang Pu Fen Xi. 2003;23:325-7 pubmed
    ..It was shown that the fluorescence spectrum of the porphyrin obtained from the superficial skin tissue of human earlobe has the same feature as that from the aqueous solution with PP IX. ..
  38. Wimmershoff F, Gardlo K, Bolsen K, Ruzicka T, Fritsch C. [High-dose vitamin therapy as prophylaxis against porphyria cutanea uremica]. Hautarzt. 2006;57:228, 230-2, 234-6 pubmed
    ..87, as opposed to the PCU group with 3.7. Considerable differences between the level of vitamin ingestion were identified between the groups. Patients with PCU took distinctly less vitamins C, E and B than patients without symptoms. ..
  39. Krishnamohan M, Qi L, Lam P, Moore M, Ng J. Urinary arsenic and porphyrin profile in C57BL/6J mice chronically exposed to monomethylarsonous acid (MMAIII) for two years. Toxicol Appl Pharmacol. 2007;224:89-97 pubmed
    ..Our results show urinary DMA(V) and porphyrin profile can be used as an early warning biomarker for chronic MMA(III) exposure before the onset of cancer. ..
  40. Lançoni G, Ravinal R, Costa R, Roselino A. Mast cells and transforming growth factor-beta expression: a possible relationship in the development of porphyria cutanea tarda skin lesions. Int J Dermatol. 2008;47:575-81 pubmed publisher
    ..The results suggest that the increased number of mast cells and of cells expressing TGF-beta, as well as their direct correlation, may contribute to the pathogenesis of the skin lesions in PCT. ..
  41. Battisti A, Morici P, Ghetti F, Sgarbossa A. Spectroscopic characterization and fluorescence imaging of Helicobacter pylori endogenous porphyrins. Biophys Chem. 2017;229:19-24 pubmed publisher
  42. Onizawa K, Okamura N, Saginoya H, Yoshida H. Characterization of autofluorescence in oral squamous cell carcinoma. Oral Oncol. 2003;39:150-6 pubmed
    ..These results suggest that the autofluorescence in oral SCC correlates with the progression of lesions, and that fluorescent substances such as protoporphyrin are produced in association with the cancerous tissue. ..
  43. Anttila J, Heinonen P, Nenonen T, Pino A, Iwai H, Kauppi E, et al. Is coproporphyrin III a copper-acquisition compound in Paracoccus denitrificans?. Biochim Biophys Acta. 2011;1807:311-8 pubmed publisher
    ..Coproporphyrin III may work as a copper-acquisition compound in P. denitrificans. ..
  44. Kellner H, Zoller W, Jacob K, Fuessl H. [Renal and enteral elimination of coproporphyrin isomers in Rotor's syndrome. A family study]. Klin Wochenschr. 1988;66:953-6 pubmed
    ..The coproporphyrin isomer I/III relation is shifted towards isomer I. Phenotypically normal relatives with normal bilirubin plasma levels may have alterations in both their renal and enteral coproporphyrin excretion. ..
  45. Azzouzi A, Steunou A, Durand A, Khalfaoui Hassani B, Bourbon M, Astier C, et al. Coproporphyrin III excretion identifies the anaerobic coproporphyrinogen III oxidase HemN as a copper target in the Cu?-ATPase mutant copA? of Rubrivivax gelatinosus. Mol Microbiol. 2013;88:339-51 pubmed publisher
    ..In light of these results and similar findings in Escherichia coli, the potential role of copper ions in the evolution of [4Fe-4S] enzymes and the Cu(+) -ATPases is discussed. ..
  46. Geier D, Pretorius H, Richards N, Geier M. A quantitative evaluation of brain dysfunction and body-burden of toxic metals. Med Sci Monit. 2012;18:CR425-31 pubmed
    ..to mild brain dysfunction had significant increases in the mean urinary concentration of uroporphyrins (uP), coproporphyrins I (cP I), and total cP (cP I + III), as well as a trend towards significantly increased mean urinary ..
  47. Hobbs C, Reid J, Shepherd M. The coproporphyrin ferrochelatase of Staphylococcus aureus: mechanistic insights into a regulatory iron-binding site. Biochem J. 2017;474:3513-3522 pubmed publisher
    ..aureus ferrochelatase, providing a molecular explanation for the observed substrate inhibition patterns. This work therefore has implications for how haem biosynthesis in S. aureus is regulated by iron availability. ..
  48. Zuijderhoudt F, Kamphuis J, Kluitenberg W, Dorresteijn de Bok J. Precision and accuracy of a HPLC method for measurement of fecal porphyrin concentrations. Clin Chem Lab Med. 2002;40:1036-9 pubmed
    ..The precision of porphyrin measurements was not influenced by the type of porphyria. Recoveries of added coproporphyrin and protoporphyrin were 90% and 108%; coefficients of variation were 6% and 19%, respectively. ..
  49. Fritsch C, Bolsen K, Ruzicka T, Goerz G. Congenital erythropoietic porphyria. J Am Acad Dermatol. 1997;36:594-610 pubmed
  50. Choi M, Yun S, Beom H, Park H, Lee J. Comparative study of the bactericidal effects of 5-aminolevulinic acid with blue and red light on Propionibacterium acnes. J Dermatol. 2011;38:661-6 pubmed publisher
    ..acnes than blue light phototherapy without the addition of ALA. However, pretreatment with ALA could enhance markedly the efficacy of red light phototherapy. ..
  51. Tanke H, de Haas R, Sagner G, Ganser M, van Gijlswijk R. Use of platinum coproporphyrin and delayed luminescence imaging to extend the number of targets FISH karyotyping. Cytometry. 1998;33:453-9 pubmed
    ..Here we introduce the concept of the use of delayed luminescence labels such as phosphorescent platinum coproporphyrins (PtCP) to extend the number of simultaneously detectable targets in multicolor FISH karyotyping...
  52. Vanden Eijnden S, Blum D, Clercx A, Goyens P, de Laet C, Vamos E. Cutaneous porphyria in a neonate with tyrosinaemia type 1. Eur J Pediatr. 2000;159:503-6 pubmed
    ..This porphyria is tentatively attributed to a secondary accumulation of coproporphyrins due to cholestasis, as reported in the bronze baby syndrome and recently described in neonates with purpuric ..
  53. Bosia J, D Ascenzo M, Borzi S, Cozzi S, Defelitto J, Curciarello J. [The Dubin-Johnson syndrome: case report and review of literature]. Acta Gastroenterol Latinoam. 2008;38:194-8 pubmed
    ..By using this methodology, we were not able to quantify the isomeric profile of the urinary coproporphyrins nor 99mTc-HIDA cholescintigraphy...