Seminars in Fetal & Neonatal Medicine
Volume 15, Issue 3 , Pages 164-168 , June 2010

Metalloporphyrins in the management of neonatal hyperbilirubinemia

References 

  1. Stevenson DK, Wong RJ, Hintz SR, Vreman HJ. The jaundiced newborn. Understanding and managing transitional hyperbilirubinemia. Minerva Pediatr. 2002;54:373–382
  2. Dennery PA, Seidman DS, Stevenson DK. Neonatal hyperbilirubinemia. N Engl J Med. 2001;344:581–590
  3. Stevenson DK, Wong RJ, DeSandre GH, Vreman HJ. A primer on neonatal jaundice. Adv Pediatr. 2004;51:263–288
  4. Kappas A, Drummond GS, Simionatto CS, Anderson KE. Control of heme oxygenase and plasma levels of bilirubin by a synthetic heme analogue, tin-protoporphyrin. Hepatology. 1984;4:336–341
  5. Stevenson DK, Rodgers PA, Vreman HJ. The use of metalloporphyrins for the chemoprevention of neonatal jaundice. Am J Dis Child. 1989;143:353–356
  6. McDonagh AF, Lightner DA. Phototherapy and the photobiology of bilirubin. Semin Liver Dis. 1988;8:272–283
  7. Vreman HJ, Wong RJ, Stevenson DK. Phototherapy: current methods and future directions. Semin Perinatol. 2004;28:326–333
  8. Watchko JF, Daood MJ, Biniwale M. Understanding neonatal hyperbilirubinaemia in the era of genomics. Semin Neonatol. 2002;7:143–152
  9. American Academy of Pediatrics . Management of hyperbilirubinemia in the newborn infant 35 or more weeks of gestation. Pediatrics. 2004;114:297–316
  10. Kaplan M, Muraca M, Hammerman C, et al. Imbalance between production and conjugation of bilirubin: a fundamental concept in the mechanism of neonatal jaundice. Pediatrics. 2002;110:e47
  11. Watchko JF. Kernicterus and the molecular mechanisms of bilirubin-induced CNS injury in newborns. Neuromolecular Med. 2006;8:513–530
  12. Watchko JF, Daood MJ, Mahmood B, Vats K, Hart C, Ahdab-Barmada M. P-glycoprotein and bilirubin disposition. J Perinatol. 2001;21(Suppl. 1):S43–S47
  13. Landaw SA, Winchell HS, Boone RF. Measurement of endogenous carbon monoxide production in hemolytic disease of the inborn. Clin Res. 1971;19:208A
  14. Maines MD. Heme oxygenase: function, multiplicity, regulatory mechanisms, and clinical applications. FASEB J. 1988;2:2557–2568
  15. Maines MD. Heme oxygenase: clinical applications and functions. Boca Raton: CRC Press; 1992;
  16. McCoubrey WK, Huang TJ, Maines MD. Isolation and characterization of a cDNA from the rat brain that encodes hemoprotein heme oxygenase-3. Eur J Biochem. 1997;247:725–732
  17. Tenhunen R, Marver HS, Schmid R. The enzymatic conversion of heme to bilirubin by microsomal heme oxygenase. Proc Natl Acad Sci USA. 1968;61:748–755
  18. Baranano DE, Rao M, Ferris CD, Snyder SH. Biliverdin reductase: a major physiologic cytoprotectant. Proc Natl Acad Sci USA. 2002;99:16093–16098
  19. Foresti R, Green CJ, Motterlini R. Generation of bile pigments by haem oxygenase: a refined cellular strategy in response to stressful insults. Biochem Soc Symp. 2004;177–192
  20. Stocker R, Yamamoto Y, McDonagh AF, Glazer AN, Ames BN. Bilirubin is an antioxidant of possible physiological importance. Science. 1987;235:1043–1046
  21. Furchgott RF, Jothianandan D. Endothelium-dependent and -independent vasodilation involving cyclic GMP: relaxation induced by nitric oxide, carbon monoxide and light. Blood Vessels. 1991;28:52–61
  22. Marks GS, Brien JF, Nakatsu K, McLaughlin BE. Does carbon monoxide have a physiological function?. Trends Pharmacol Sci. 1991;12:185–188
  23. Acevedo CH, Ahmed A. Hemeoxygenase-1 inhibits human myometrial contractility via carbon monoxide and is upregulated by progesterone during pregnancy. J Clin Invest. 1998;101:949–955
  24. Brune B, Ullrich V. Inhibition of platelet aggregation by carbon monoxide is mediated by activation of guanylate cyclase. Mol Pharmacol. 1987;32:497–504
  25. Brouard S, Otterbein LE, Anrather J, et al. Carbon monoxide generated by heme oxygenase 1 suppresses endothelial cell apoptosis. J Exp Med. 2000;192:1015–1026
  26. Prabhakar NR, Dinerman JL, Agani FH, Snyder SH. Carbon monoxide: a role in carotid body chemoreception. Proc Natl Acad Sci USA. 1995;92:1994–1997
  27. Leinders-Zufall T, Shepherd GM, Zufall F. Regulation of cyclic nucleotide-gated channels and membrane excitability in olfactory receptor cells by carbon monoxide. J Neurophysiol. 1995;74:1498–1508
  28. Ryter SW, Otterbein LE, Morse D, Choi AM. Heme oxygenase/carbon monoxide signaling pathways: regulation and functional significance. Mol Cell Biochem. 2002;234–235:249–263
  29. Cudmore M, Ahmad S, Al-Ani B, et al. Negative regulation of soluble Flt-1 and soluble endoglin release by heme oxygenase-1. Circulation. 2007;115:1789–1797
  30. Loboda A, Jazwa A, Grochot-Przeczek A, et al. Heme oxygenase-1 and the vascular bed: from molecular mechanisms to therapeutic opportunities. Antioxid Redox Signal. 2008;10:1767–1812
  31. Odrcich MJ, Graham CH, Kimura KA, et al. Heme oxygenase and nitric oxide synthase in the placenta of the guinea pig during gestation. Placenta. 1998;19:509–516
  32. Appleton SD, Chretien ML, McLaughlin BE, et al. Selective inhibition of heme oxygenase, without inhibition of nitric oxide synthase or soluble guanylyl cyclase, by metalloporphyrins at low concentrations. Drug Metab Dispos. 1999;27:1214–1219
  33. Stevenson DK, Vreman HJ. Carbon monoxide and bilirubin production in neonates. Pediatrics. 1997;100:252–254
  34. Vreman HJ, Wong RJ, Sanesi CA, Dennery PA, Stevenson DK. Simultaneous production of carbon monoxide and thiobarbituric acid reactive substances in rat tissue preparations by an iron–ascorbate system. Can J Physiol Pharmacol. 1998;76:1057–1065
  35. Kaplan M, Na'amad M, Kenan A, et al. Failure to predict hemolysis and hyperbilirubinemia by IgG subclass in blood group A or B infants born to group O mothers. Pediatrics. 2009;123:e132–e137
  36. Ostrander CR, Cohen RS, Hopper AO, Cowan BE, Stevens GB, Stevenson DK. Paired determinations of blood carboxyhemoglobin concentration and carbon monoxide excretion rate in term and preterm infants. J Lab Clin Med. 1982;100:745–755
  37. Drummond GS, Kappas A. Prevention of neonatal hyperbilirubinemia by tin protoporphyrin IX, a potent competitive inhibitor of heme oxidation. Proc Natl Acad Sci USA. 1981;78:6466–6470
  38. Maines MD. Zinc-protoporphyrin is a selective inhibitor of heme oxygenase activity in the neonatal rat. Biochim Biophys Acta. 1981;673:339–350
  39. Cornelius CE, Rodgers PA. Prevention of neonatal hyperbilirubinemia in rhesus monkeys by tin-protoporphyrin. Pediatr Res. 1984;18:728–730
  40. Stout DL, Becker FF. The effects of tin-protoporphyrin administration on hepatic xenobiotic metabolizing enzymes in the juvenile rat. Drug Metab Dispos. 1988;16:23–26
  41. Davis DR, Bail SP. Tin-protoporphyrin suppression of hyperbilirubinemia in the jaundiced Gunn rat. Dev Pharmacol Ther. 1988;11:281–287
  42. Land EJ, McDonagh AF, McGarvey DJ, Truscott TG. Photophysical studies of tin(IV)-protoporphyrin: potential phototoxicity of a chemotherapeutic agent proposed for the prevention of neonatal jaundice. Proc Natl Acad Sci USA. 1988;85:5249–5253
  43. Mitrione SM, Villalon P, Lutton JD, Levere RD, Abraham NG. Inhibition of human adult and fetal heme oxygenase by new synthetic heme analogues. Am J Med Sci. 1988;296:180–186
  44. Valaes TN, Harvey-Wilkes K. Pharmacologic approaches to the prevention and treatment of neonatal hyperbilirubinemia. Clin Perinatol. 1990;17:245–273
  45. Kappas A, Drummond GS, Manola T, Petmezaki S, Valaes T. Sn-protoporphyrin use in the management of hyperbilirubinemia in term newborns with direct Coombs-positive ABO incompatibility. Pediatrics. 1988;81:485–497
  46. Martinez JC, Garcia HO, Otheguy LE, Drummond GS, Kappas A. Control of severe hyperbilirubinemia in full-term newborns with the inhibitor of bilirubin production Sn-mesoporphyrin. Pediatrics. 1999;103:1–5
  47. Valaes T, Petmezaki S, Henschke C, Drummond GS, Kappas A. Control of jaundice in preterm newborns by an inhibitor of bilirubin production: studies with tin-mesoporphyrin. Pediatrics. 1994;93:1–11
  48. Reddy P, Najundaswamy S, Mehta R, Petrova A, Hegyi T. Tin-mesoporphyrin in the treatment of severe hyperbilirubinemia in a very-low-birth-weight infant. J Perinatol. 2003;23:507–508
  49. Keino H, Nagae H, Mimura S, Watanabe K, Kashiwamata S. Dangerous effects of tin-protoporphyrin plus photoirradiation on neonatal rats. Eur J Pediatr. 1990;149:278–279
  50. Hintz SR, Vreman HJ, Stevenson DK. Mortality of metalloporphyrin-treated neonatal rats after light exposure. Dev Pharmacol Ther. 1990;14:187–192
  51. Vreman HJ, Gillman MJ, Downum KR, Stevenson DK. In vitro generation of carbon monoxide from organic molecules and synthetic metalloporphyrins mediated by light. Dev Pharmacol Ther. 1990;15:112–124
  52. Wong RJ, Morioka I, Vreman HJ, Stevenson DK. Oral absorptivity of tin mesoporphyrin (SnMP) and distribution into the brain of young mice. Pediatr Res. 2005;57:A1277
  53. Morioka I, Wong RJ, Muchova L, Vreman HJ, Stevenson DK. Effect of tin mesoporphyrin on heme oxygenase activity following repeated heme loads in newborn mice. 2006;EPAS2006; 59:5575.485
  54. Wong RJ, Bhutani VK, Vreman HJ, Stevenson DK. Tin mesoporphyrin for the prevention of severe neonatal hyperbilirubinemia. NeoReviews. 2007;8:e77–e84
  55. Vreman HJ, Wong RJ, Stevenson DK. Alternative metalloporphyrins for the treatment of neonatal jaundice. J Perinatol. 2001;21(Suppl. 1):S108–S113
  56. Morisawa T, Wong RJ, Xiao H, Bhutani VK, Vreman HJ, Stevenson DK. Inhibition of heme oxygenase activity by chromium mesoporphyrin in the heme-loaded newborn mouse. 2008;E-PAS2008:6130.9
  57. He CX, Morisawa T, Zhao H, Wong RJ, Stevenson DK. Age-dependent expression of heme oxygenase-1 in mice following oral administration of chromium mesoporphyrin. J Invest Med. 2009;57:177;(#286)
  58. Vreman HJ, Lee OK, Stevenson DK. In vitro and in vivo characteristics of a heme oxygenase inhibitor: ZnBG. Am J Med Sci. 1991;302:335–341
  59. Campbell CM, Morisawa T, Zhao H, Wong RJ, Stevenson DK. Dose-dependent effects of zinc bis glycol porphyrin on the expression of heme oxygenase in newborn mice. J Invest Med. 2009;57:177;(#287)
  60. Hajdena-Dawson M, Zhang W, Contag PR, et al. Effects of metalloporphyrins on heme oxygenase-1 transcription: correlative cell culture assays guide in vivo imaging. Molec Imag. 2003;2:138–149
  61. Zhang W, Contag PR, Hardy J, et al. Selection of potential therapeutics based on in vivo spatiotemporal transcription patterns of heme oxygenase-1. J Mol Med. 2002;80:655–664
  62. Xiao H, Morisawa T, Wong RJ, Stevenson DK. Short- and long-term effects of heme oxygenase activity by chromium mesoporphyrin in newborn mice. E-PAS. 2008;2008:6130.8
  63. Morris BH, Oh W, Tyson JE, et al. Aggressive vs. conservative phototherapy for infants with extremely low birth weight. N Engl J Med. 2008;359:1885–1896
  64. Iyer S, Woo J, Cornejo MC, et al. Characterization and biological significance of immunosuppressive peptide D2702.75-84 (E → V) binding protein. Isolation of heme oxygenase-1. J Biol Chem. 1998;273:2692–2697
  65. Vlahakis JZ, Kinobe RT, Bowers RJ, Brien JF, Nakatsu K, Szarek WA. Synthesis and evaluation of azalanstat analogues as heme oxygenase inhibitors. Bioorg Medi Chem Lett. 2005;15:1457–1461
  66. Vlahakis JZ, Kinobe RT, Bowers RJ, Brien JF, Nakatsu K, Szarek WA. Imidazole-dioxolane compounds as isozyme-selective heme oxygenase inhibitors. J Med Chemy. 2006;49:4437–4441
  67. Morisawa T, Wong RJ, Bhutani VK, Vreman HJ, Stevenson DK. Inhibition of heme oxygenase activity in newborn mice by azalanstat. Can J Physiol Pharmacol. 2008;86:651–659
  68. Kinobe RT, Vlahakis JZ, Vreman HJ, et al. Selectivity of imidazole-dioxolane compounds for in vitro inhibition of microsomal haem oxygenase isoforms. Br J Pharmacol. 2006;147:307–315
  69. Lin Z, Fontaine J, Watchko JF. Coexpression of gene polymorphisms involved in bilirubin production and metabolism. Pediatrics. 2008;122:e156–e162
  70. Kaplan M, Hammerman C, Rubaltelli FF, et al. Hemolysis and bilirubin conjugation in association with UDP-glucuronosyltransferase 1A1 promoter polymorphism. Hepatology. 2002;35:905–911
  71. Kaplan M, Renbaum P, Levy-Lahad E, Hammerman C, Lahad A, Beutler E. Gilbert syndrome and glucose-6-phosphate dehydrogenase deficiency: a dose-dependent genetic interaction crucial to neonatal hyperbilirubinemia. Proc Natl Acad Sci USA. 1997;94:12128–12132
  72. Kaplan M, Hammerman C. Glucose-6-phosphate dehydrogenase deficiency: a hidden risk for kernicterus. Semin Perinatol. 2004;28:356–364

PII: S1744-165X(09)00111-5

doi: 10.1016/j.siny.2009.11.004

Seminars in Fetal & Neonatal Medicine
Volume 15, Issue 3 , Pages 164-168 , June 2010

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