Insights into the Structures of Bilirubin and Biliverdin from Vibrational and Electronic Circular Dichroism: History and Perspectives

Year: 2023

Authors: Longhi G., Ghidinelli S., Abbate S., Mazzeo G., Fusi M., Boiadjiev S.E., Lightner D.A.

Autors Affiliation: Univ Brescia, Dipartimento Med Mol & Traslaz, Viale Europa 11, I-25123 Brescia, Italy; CNR, INO, Res Unit Brescia, CSMT Via Branze 45, I-25123 Brescia, Italy; Reg Hlth Inspectorate, 7 Prince Al Battenberg 1 Str, Pleven 5800, Bulgaria; Univ Nevada, Chem Dept, Reno, NV 89557 USA.

Abstract: In this work we review research activities on a few of the most relevant structural aspects of bilirubin (BR) and biliverdin (BV). Special attention is paid to the exocyclic C=C bonds being in mostly Z rather than E configurations, and to the overall conformation being essentially different for BR and BV due to the presence or absence of the double C=C bond at C-10. In both cases, racemic mixtures of each compound of either M or P configuration are present in achiral solutions; however, imbalance between the two configurations may be easily achieved. In particular, results based on chiroptical spectroscopies, both electronic and vibrational circular dichroism (ECD and VCD) methods, are presented for chirally derivatized BR and BV molecules. Finally, we review deracemization experiments monitored with ECD data from our lab for BR in the presence of serum albumin and anesthetic compounds.

Journal/Review: MOLECULES

Volume: 28 (6)      Pages from: 2564-1  to: 2564-18

More Information: Funding was provided by the Italian Ministry MIUR for the project: PRIN 2017, Project Physicochemical Heuristic Approaches: Nanoscale Theory of Molecular Spectroscopy (PHANTOMS), prot. 2017A4XRCA). Chemistry Department, University of Nevada Reno, provided travel money for planning and preparing the manuscript.
KeyWords: bilirubin; biliverdin; structural and configurational aspects; circular dichroism; deracemization; anesthetics
DOI: 10.3390/molecules28062564

Citations: 5
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