The Biological Effects of Bilirubin Photoisomers
Jazyk angličtina Země Spojené státy americké Médium electronic-ecollection
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
26829016
PubMed Central
PMC4735493
DOI
10.1371/journal.pone.0148126
PII: PONE-D-15-20575
Knihovny.cz E-zdroje
- MeSH
- bilirubin chemie izolace a purifikace farmakologie MeSH
- buněčné linie MeSH
- buněčný cyklus účinky léků MeSH
- cirkulární dichroismus MeSH
- fototerapie MeSH
- hem metabolismus MeSH
- isomerie MeSH
- kinetika MeSH
- lidé MeSH
- ligandy MeSH
- regulace genové exprese účinky léků MeSH
- sérový albumin metabolismus MeSH
- spektrofotometrie ultrafialová MeSH
- světlo * MeSH
- viabilita buněk účinky léků MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- bilirubin MeSH
- hem MeSH
- ligandy MeSH
- sérový albumin MeSH
Although phototherapy was introduced as early as 1950's, the potential biological effects of bilirubin photoisomers (PI) generated during phototherapy remain unclear. The aim of our study was to isolate bilirubin PI in their pure forms and to assess their biological effects in vitro. The three major bilirubin PI (ZE- and EZ-bilirubin and Z-lumirubin) were prepared by photo-irradiation of unconjugated bilirubin. The individual photoproducts were chromatographically separated (TLC, HPLC), and their identities verified by mass spectrometry. The role of Z-lumirubin (the principle bilirubin PI) on the dissociation of bilirubin from albumin was tested by several methods: peroxidase, fluorescence quenching, and circular dichroism. The biological effects of major bilirubin PI (cell viability, expression of selected genes, cell cycle progression) were tested on the SH-SY5Y human neuroblastoma cell line. Lumirubin was found to have a binding site on human serum albumin, in the subdomain IB (or at a close distance to it); and thus, different from that of bilirubin. Its binding constant to albumin was much lower when compared with bilirubin, and lumirubin did not affect the level of unbound bilirubin (Bf). Compared to unconjugated bilirubin, bilirubin PI did not have any effect on either SH-SY5Y cell viability, the expression of genes involved in bilirubin metabolism or cell cycle progression, nor in modulation of the cell cycle phase. The principle bilirubin PI do not interfere with bilirubin albumin binding, and do not exert any toxic effect on human neuroblastoma cells.
Faculty of Science Charles University Prague Prague Czech Republic
Institute of Chemical Technology Prague Prague Czech Republic
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Cremer RJ, Perryman PW, Richards DH. Influence of light on the hyperbilirubinaemia of infants. Lancet. 1958; 1: 1094–1097. PubMed
Onishi S, Isobe K, Itoh S, Kawade N, Sugiyama S. Demonstration of a geometric isomer of bilirubin-IX alpha in the serum of a hyperbilirubinaemic newborn infant and the mechanism of jaundice phototherapy. Biochem J. 1980; 190: 533–536. PubMed PMC
Onishi S, Miura I, Isobe K, Itoh S, Ogino T, Yokoyama T, et al. Structure and thermal interconversion of cyclobilirubin IX alpha. Biochem J. 1984; 218: 667–676. PubMed PMC
McDonagh AF, Palma LA. Phototherapy for neonatal jaundice. Stereospecific and regioselective photoisomerization of bilirubin bound to human serum albumin and NMR characterization of intramolecularly cyclized photoproducts. J Am Chem Soc. 1982; 104: 6867–6869.
Lightner DA, McDonagh AF. Molecular mechanisms of phototherapy for neonatal jaundice. Acc Chem Res. 1984; 17: 417–424.
Knobloch E, Mandys F, Hodr R, Hujer R, Mader R. Study of the mechanism of the photoisomerization and photooxidation of bilirubin using a model for the phototherapy of hyperbilirubinemia. J Chromatogr. 1991; 566: 89–99. PubMed
Xiong T, Qu Y, Cambier S, Mu D. The side effects of phototherapy for neonatal jaundice: what do we know? What should we do? Eur J Pediatr. 2011; 170: 1247–1255. 10.1007/s00431-011-1454-1 PubMed DOI
Tatli MM, Minnet C, Kocyigit A, Karadag A. Phototherapy increases DNA damage in lymphocytes of hyperbilirubinemic neonates. Mutat Res. 2008; 654: 93–95. 10.1016/j.mrgentox.2007.06.013 PubMed DOI
Beken S, Aydin B, Zencirogglu A, Dilli D, Ozkan E, Dursun A, et al. The effects of phototherapy on eosinophil and eosinophilic cationic protein in newborns with hyperbilirubinemia. Fetal Pediatr Pathol. 2014; 33: 151–156. 10.3109/15513815.2014.883456 PubMed DOI
Raghavan K, Thomas E, Patole S, Muller R. Is phototherapy a risk factor for ileus in high-risk neonates? J Matern Fetal Neonatal Med. 2005; 18: 129–131. PubMed
Arnold C, Pedroza C, Tyson JE. Phototherapy in ELBW newborns: Does it work? Is it safe? The evidence from randomized clinical trials. Semin Perinatol. 2014; 38: 452–464. 10.1053/j.semperi.2014.08.008 PubMed DOI
Tyson JE, Pedroza C, Langer J, Green C, Morris B, Stevenson D, et al. Does aggressive phototherapy increase mortality while decreasing profound impairment among the smallest and sickest newborns? J Perinatol. 2012; 32: 677–684. 10.1038/jp.2012.64 PubMed DOI PMC
Ostrow JD, Pascolo L, Shapiro SM, Tiribelli C. New concepts in bilirubin encephalopathy. Eur J Clin Invest. 2003; 33: 988–997. PubMed
Calligaris SD, Bellarosa C, Giraudi P, Wennberg RP, Ostrow JD, Tiribelli C. Cytotoxicity is predicted by unbound and not total bilirubin concentration. Pediatr Res. 2007; 62: 576–580. PubMed
Ahlfors CE, Wennberg RP. Bilirubin-albumin binding and neonatal jaundice. Semin Perinatol. 2004; 28: 334–339. PubMed
Roll EB. Bilirubin-induced cell death during continuous and intermittent phototherapy and in the dark. Acta Paediatr. 2005; 94: 1437–1442. PubMed
Roll EB, Christensen T. Formation of photoproducts and cytotoxicity of bilirubin irradiated with turquoise and blue phototherapy light. Acta Paediatr. 2005; 94: 1448–1454. PubMed
Roll EB, Christensen T, Gederaas OA. Effects of bilirubin and phototherapy on osmotic fragility and haematoporphyrin-induced photohaemolysis of normal erythrocytes and spherocytes. Acta Paediatr. 2005; 94: 1443–1447. PubMed
Christensen T, Roll EB, Jaworska A, Kinn G. Bilirubin- and light induced cell death in a murine lymphoma cell line. J Photochem Photobiol B. 2000; 58: 170–174. PubMed
Christensen T, Kinn G, Granli T, Amundsen I. Cells, bilirubin and light: formation of bilirubin photoproducts and cellular damage at defined wavelengths. Acta Paediatr. 1994; 83: 7–12. PubMed
Christensen T, Reitan JB, Kinn G. Single-strand breaks in the DNA of human cells exposed to visible light from phototherapy lamps in the presence and absence of bilirubin. J Photochem Photobiol B. 1990; 7: 337–346. PubMed
Silberberg D, Johnson L, Schutta H, Ritter L. Photodegradation products of bilirubin studied in myelinating cerebellum cultures. Birth Defects Orig Artic Ser. 1970; 6: 119–123. PubMed
Silberberg DH, Johnson L, Schutta H, Ritter L. Effects of photodegradation products of bilirubin on myelinating cerebellum cultures. J Pediatr 1970; 77: 613–618. PubMed
McDonagh AF, Assisi F. The ready isomerization of bilirubin IX-a in aqueous solution. Biochem J. 1972; 129: 797–800. PubMed PMC
Stoll MS, Zenone EA, Ostrow JD, Zarembo JE. Preparation and properties of bilirubin photoisomers. Biochem J. 1979; 183: 139–146. PubMed PMC
Stoll MS, Vicker N, Gray CH, Bonnett R. Concerning the structure of photobilirubin II. Biochem J. 1982; 201: 179–188. PubMed PMC
Bonnett R, Buckley DG, Hamzetash D, Hawkes GE, Ioannou S, Stoll MS. Photobilirubin II. Biochem J. 1984; 219: 1053–1056. PubMed PMC
McDonagh AF, Agati G, Fusi F, Pratesi R. Quantum yields for laser photocyclization of bilirubin in the presence of human serum albumin. Dependence of quantum yield on excitation wavelength. Photochem Photobiol. 1989; 50: 305–319. PubMed
McDonagh AF, Palma LA, Trull FR, Lightner DA. Phototherapy for neonatal jaundice. Configurational isomers of bilirubin. J Am Chem Soc. 1982; 104: 6865–6869.
Lakowicz JR (2006) Principles of fluorescence spectroscopy. New York: Springer; xxvi, 954 p. p.
Goncharova I, Orlov S, Urbanova M. The location of the high- and low-affinity bilirubin-binding sites on serum albumin: ligand-competition analysis investigated by circular dichroism. Biophys Chem. 2013; 180–181: 55–65. 10.1016/j.bpc.2013.06.004 PubMed DOI
Royer RE, Vander Jagt DL. Gossypol binds to a high-affinity binding site on human serum albumin. FEBS Lett. 1983; 157: 28–30. PubMed
Brodersen R. Binding of bilirubin to albumin. CRC Crit Rev Clin Lab Sci. 1980; 11: 305–399. PubMed
Goncharova I, Urbanova M. Stereoselective bile pigment binding to polypeptides and albumins: a circular dichroism study. Anal Bioanal Chem. 2008; 392: 1355–1365. 10.1007/s00216-008-2427-8 PubMed DOI
Zsila F. Subdomain IB is the third major drug binding region of human serum albumin: toward the three-sites model. Mol Pharm. 2013; 10: 1668–1682. 10.1021/mp400027q PubMed DOI
Ahlfors CE. Measurement of plasma unbound unconjugated bilirubin. Anal Biochem. 2000; 279: 130–135. PubMed
Mreihil K, McDonagh AF, Nakstad B, Hansen TW. Early isomerization of bilirubin in phototherapy of neonatal jaundice. Ped Res. 2010; 67: 656–659. PubMed
Vandesompele J, De Preter K, Pattyn F, Poppe B, Van Roy N, De Paepe A, et al. Accurate normalization of real-time quantitative RT-PCR data by geometric averaging of multiple internal control genes. Genome Biol. 2002; 3: RESEARCH0034 PubMed PMC
Bustin SA, Benes V, Garson JA, Hellemans J, Huggett J, Kubista M, et al. The MIQE guidelines: minimum information for publication of quantitative real-time PCR experiments. Clin Chem. 2009; 55: 611–622. 10.1373/clinchem.2008.112797 PubMed DOI
Vreman HJ, Wong RJ, Kadotani T, Stevenson DK. Determination of carbon monoxide (CO) in rodent tissue: effect of heme administration and environmental CO exposure. Anal Biochem. 2005; 341: 280–289. PubMed
Vitek L, Schwertner HA. The heme catabolic pathway and its protective effects on oxidative stress-mediated diseases. Adv Clin Chem. 2007; 43: 1–57. PubMed
Abraham NG, Kappas A. Pharmacological and clinical aspects of heme oxygenase. Pharmacol Rev. 2008; 60: 79–127. 10.1124/pr.107.07104 PubMed DOI
Gazzin S, Berengeno AL, Strazielle N, Fazzari F, Raseni A, Ostrow JD, et al. Modulation of Mrp1 (ABCc1) and Pgp (ABCb1) by bilirubin at the blood-CSF and blood-brain barriers in the Gunn rat. PLoS One. 2011; 6: e16165 10.1371/journal.pone.0016165 PubMed DOI PMC
Rigato I, Pascolo L, Fernetti C, Ostrow JD, Tiribelli C. The human multidrug-resistance-associated protein MRP1 mediates ATP-dependent transport of unconjugated bilirubin. Biochem J. 2004; 383: 335–341. PubMed PMC
Pestell RG. New roles of cyclin D1. Am J Pathol. 2013; 183: 3–9. 10.1016/j.ajpath.2013.03.001 PubMed DOI PMC
Moroy T, Geisen C. Cyclin E. Int J Biochem Cell Biol. 2004; 36: 1424–1439. PubMed
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