Inverse Raman Spectroscopy of Bilirubin and its Ditauride

The inverse Raman spectrum of bilirubin and bilirubin ditauride were measured under pre-resonant conditions. Spectra in chloroform and dimethyl sulfoxide were assigned by comparison with model compounds and on the basis of the known effects of the solvents on the internal hydrogen bonding in bilirubin. The band assignments were used to interpret the spectra of bilirubin ditauride in aqueous solution. Evidence is presented for strong hydrogen bonding to the pyrrole NH bonds and to the lactam rings. It is proposed that hydrogen bonding to water is facilitated by photoactivation and, in turn, stabilizes photohiliruhin.

[1]  D. Lightner,et al.  Phototherapy for neonatal jaundice. Configurational isomers of bilirubin , 1982 .

[2]  H. Falk,et al.  The structure of “photobilirubin” , 1982 .

[3]  Kevin M. Smith,et al.  Vinyl influences on protoheme resonance Raman spectra: nickel(II) protoporphyrin IX with deuterated vinyl groups , 1982 .

[4]  J. Flores,et al.  QUANTUM YIELD and EQUILIBRIUM POSITION OF THE CONFIGURATIONAL PHOTOISOMERIZATION OF BILIRUBIN BOUND TO HUMAN SERUM ALBUMIN * , 1982, Photochemistry and photobiology.

[5]  G. Navon,et al.  Studies of the conformation of bilirubin and its dimethyl ester in dimethyl sulphoxide solutions by nuclear magnetic resonance. , 1982, The Biochemical journal.

[6]  T. Birchall,et al.  Proton, carbon-13, and phosphorus-31 NMR study of primary and secondary phenylamines, -phosphines, and -arsines and their anions , 1982 .

[7]  M. Morris,et al.  Applications of Resonance Inverse Raman and Raman Gain Spectroscopy to Biological Systems , 1982 .

[8]  M. Morris,et al.  Inverse Raman and Raman Gain Spectra of Liquids and Solutions , 1982 .

[9]  N. Vicker,et al.  Concerning the structure of photobilirubin II. , 1982, The Biochemical journal.

[10]  G. Navon,et al.  Nuclear magnetic resonance studies of the conformation of bilirubin and its derivatives in solution , 1982 .

[11]  A. Mcdonagh.  Phototherapy: a new twist to bilirubin. , 1981, Jornal de Pediatria.

[12]  G. Navon,et al.  Carbon‐13 nuclear magnetic resonance study of the motional behaviour of bilirubin and of some of its derivatives , 1981 .

[13]  M. Lippitsch.  Surface enhanced raman spectra of biliverdine and pyrromethenone adsorbed to silver colloids , 1981 .

[14]  Y. Mauguen,et al.  The structure of triclinic bilirubin chloroform–methanol solvate , 1980 .

[15]  Brown Ak,et al.  Phototherapy for neonatal hyperbilirubinemia: efficacy, mechanism and toxicity. , 1980, Advances in pediatrics.

[16]  R. Brodersen,et al.  Binding of bilirubin to albumin. , 1980, CRC critical reviews in clinical laboratory sciences.

[17]  D. Lightner,et al.  Configurational isomerization of bilirubin and the mechanism of jaundice phototherapy. , 1979, Biochemical and biophysical research communications.

[18]  M. Stockburger,et al.  Spectroscopic studies on model compounds of the phytochrome chromophore. Protonation and deprotonation of biliverdin dimethyl ester , 1979 .

[19]  D. Lightner,et al.  Geometric isomerisation of bilirubin-IXα and its dimethyl ester , 1979 .

[20]  D. Lightner,et al.  Photobilirubin: an early bilirubin photoproduct detected by absorbance difference spectroscopy. , 1979, Proceedings of the National Academy of Sciences of the United States of America.

[21]  H. Falk,et al.  Beiträge zur Chemie der Pyrrolpigmente, XV. Die Lactam-Lactim-Tautomerie von Gallenpigmenten , 1977 .

[22]  H. Falk,et al.  Beiträge zur Chemie der Pyrrolpigmente, 16. Mitt.: 5-[5-Methyliden-(5H-pyrrolyl-2-methyliden)]-3-pyrrolin-2-on — eine Partialstruktur von Gallenpigmenten , 1977 .

[23]  R. Bonnett,et al.  Structure of bilirubin , 1976, Nature.

[24]  H. Falk,et al.  Das tautomere Gleichgewicht des Bilirubins Kurze Mitteilung , 1976 .

[25]  P. Manitto,et al.  Free-energy barrier of conformational inversion in bilirubin , 1976 .

[26]  J. Lucey,et al.  The effects of light on the newly born infant. , 1973, Journal of perinatal medicine.

[27]  M. Forel,et al.  N° 109. — Étude du spectre de vibration du δ-valérolactame et de quelques molécules substituées - I. — δ-Valérolactme et dérivés deutériés , 1970 .

[28]  G. Thomas,et al.  Raman spectral studies of nucleic acids and related molecules—I Ribonucleic acid derivatives , 1967 .

[29]  N. Suzuki,et al.  Infrared spectra of bilirubin and calcium bilirubinate. , 1967, Chemical & pharmaceutical bulletin.

[30]  R. Brodersen,et al.  Intramolecular hydrogen bonding in bilirubin. , 1967, Acta chemica Scandinavica.

[31]  B. T. Newbold,et al.  PHYSICAL PROPERTIES OF COMMERCIAL BILIRUBINS. , 1964, Canadian journal of biochemistry.

[32]  B. T. Newbold,et al.  PREPARATIONS OF DIALKYLAZOXYBENZENES AND THEIR DERIVATIVES , 1964 .

[33]  E. Jellum,et al.  Structure of Bilirubin , 1963, Nature.

[34]  R. Cremer,et al.  INFLUENCE OF LIGHT ON THE HYPERBILIRUBINÆMIA OF INFANTS , 1958 .