Abstract
The success of phototherapy depends on photochemical transformations of bilirubin within light-exposed tissues. These reactions alter the structure of bilirubin in such a way that the intact molecule or fragments of it can be excreted via the kidney or liver without having to undergo further metabolic modification. So far three photochemical reactions of bilirubin have been shown to occur in vivo, and it is likely that these three together account for most of the effect of light on bilirubin metabolism in jaundiced newborns. The three reactions are photooxidation, configurational isomerization, and structural isomerization. In this presentation I shall discuss briefly some of our evidence for the occurrence of these reactions in vivo and speculate on their relative contributions to the net effect of phototherapy. Since the interpretation of the in vivo studies is very much dependent on knowledge gleaned from in vitro photochemical studies, I shall begin with a discussion of the latter.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
D.A. Lightner, Structure, photochemistry, and organic chemistry of bilirubin, in: “Bilirubin”, K.P.M. Heirwegh and S.B. Brown, eds., CRC Press, Boca Raton (1982).
D.A. Lightner, W.P. Linnane, and C.E. Ahlfors, Bilirubin photooxidation products in the urine of phototherapy neonates, Submitted for publication.
A.F. McDonagh, D.A. Lightner, and T.A. Wooldridge, Geometric isomerization of bilirubin-IXa and its dimethyl ester. J. Chem. Soc. Chem. Commun. 110 (1979).
R. Bonnett, J.E. Davis, M.B. Hursthouse, and G.M. Sheldrick, The structure of bilirubin, Proc. Roy. Soc. Lond. B. 202: 249 (1978).
A.F. McDonagh, L.A. Palma, F.R. Trull, and D.A. Lightner, Phototherapy for neonatal jaundice. Configurational isomers of bilirubin, J. Am. Chem. Soc. 102: 6865 (1982).
H. Falk, N. Muller, M. Ratzenhofer, and K. Winsauer, The structure of “Photobilirubin”, Monatsh. Chem. 113:1421 (1982).
J.F. Ennever, A.F. McDonagh, and W.T. Speck, Phototherapy for neonatal jaundice: Optimal wavelengths of light, J. Pediatr. In press.
J.A. de Groot, R. van der Steen, R. Fokkens, and J. Lugtenburg, Synthesis and photoisomerisation of 2,3,17,18,22-pentamethyl-10,23-dihydro-1,19-[21H,24H]-bilindione, an unsymmetrical bilirubin model compound, Recl. Tray. Chim. Pays-Bas 101:219 (1982).
J.A. de Groot, R. van der Steen, R. Fokkens, and J. Lugtenburg, Synthesis and photochemical reactivity of bilirubin model compounds, Recl. Tray. Chim. Pays-Bas 101:35 (1982).
A.F. McDonagh, L.A. Palma, and D.A. Lightner, 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. 104:6867 (1982).
B.I. Green, A.A. Lamola, and C.V. Shank, Picosecond primary photoprocesses of bilirubin bound to human serum albumin, Proc. Natl. Acad. Sci. USA 78:2008 (1981).
M.S. Stoll, N. Vicker, C.H. Gray, and R. Bonnett, Concerning the structure of photobilirubin II, Biochem. J. 201:179 (1982).
M.S. Stoll, E.A. Zenone, J.D. Ostrow, and J.E. Zarembo, Preparation and properties of bilirubin photoisomers, Biochem. J. 183:139 (1979).
S. Onishi, K. Isobe, S. Itoh, N. Kawade, and S. Sugiyama, Demonstration of a geometric isomer of bilirubin-IX in the serum of a hyperbilirubinaemic newborn infant and the mechanism of jaundice phototherapy, Biochem. J. 190:533 (1980).
A.F. McDonagh, Bile Pigments: Bilatrienes and 5,15-biladienes, in: “The Porphyrins”, D. Dolphin, ed., Academic Press, New York (1979).
S. Onishi, S. Itoh, N. Kawade, K. Isobe, and S. Sugiyama, The separation of configurational isomers of bilirubin by high pressure liquid chromatography and the mechanism of jaundice phototherapy, Biochem. Biophys. Res. Commun. 90:890 (1979).
A.F. McDonagh, and L.M. Ramonas, Jaundice phototherapy: Micro flow-cell photometry reveals rapid biliary response of Gunn rats to light, Science 201: 829 (1978).
C.S. Berry, J.E. Zarembo, and J.D. Ostrow, Evidence for conversion of bilirubin to dihydroxyl derivatives in the Gunn rat, Biochem. Biophys. Res. Commun. 49:1366 (1972).
A.F. McDonagh, L.A. Palma, and D.A. Lightner, Blue light and bilirubin excretion, Science 208: 145 (1980).
A.F. McDonagh, unpublished observations.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1984 Springer Science+Business Media New York
About this chapter
Cite this chapter
McDonagh, A.F. (1984). Molecular Mechanisms of Phototherapy of Neonatal Jaundice. In: Rubaltelli, F.F., Jori, G. (eds) Neonatal Jaundice. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-7517-3_17
Download citation
DOI: https://doi.org/10.1007/978-1-4684-7517-3_17
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4684-7519-7
Online ISBN: 978-1-4684-7517-3
eBook Packages: Springer Book Archive