Metalloporphyrins in the management of neonatal hyperbilirubinemia

Seminars in Fetal and Neonatal Medicine

Volumn 15, Issue 3, 2010, Pages 164-168

  Stevenson, David K ^a   Wong, Ronald J ^a  

^a STANFORD UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Bilirubin; Heme oxygenase; Hyperbilirubinemia; Metalloporphyrin; Neonatal jaundice

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; AZALANSTAT; BILIRUBIN; CARBON MONOXIDE; CHROMIUM MESOPORPHYRIN; HEME OXYGENASE; HEME OXYGENASE INHIBITOR; IMIDAZOLE DIOXOLANE; MESOPORPHYRIN TIN; METALLOPORPHYRIN; PORPHYRIN DERIVATIVE; PROTOPORPHYRIN TIN; PROTOPORPHYRIN ZINC; UNCLASSIFIED DRUG; ZINC DEUTEROPORPHYRIN BIS GLYCOL;

ARTICLE; BIOSYNTHESIS; CATABOLISM; DOSE RESPONSE; DRUG ABSORPTION; DRUG MECHANISM; DRUG MEGADOSE; ENZYME INHIBITION; HEMOLYSIS; HUMAN; NEWBORN JAUNDICE; NONHUMAN;

BILIRUBIN; HEME OXYGENASE (DECYCLIZING); HUMANS; HYPERBILIRUBINEMIA, NEONATAL; INFANT, NEWBORN; METALLOPORPHYRINS;

EID: 77953290641     PISSN: 1744165X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.siny.2009.11.004     Document Type: Article

References (72)

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