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@article{1863612,
author = {Madea, Dominik and Mujawar, Taufiqueahmed Pirsaheb and Dvořák, Aleš and Pospíšilová, Kateřina and Muchová, Lucie and Čubáková, Petra and Kloz, Miroslav and Švenda, Jakub and Vítek, Libor and Klán, Petr},
article_number = {5},
doi = {http://dx.doi.org/10.1021/acs.joc.1c02870},
keywords = {Alcohols; Molecular structure; Photooxidation; Quantum mechanics; Quantum yield},
language = {eng},
issn = {0022-3263},
journal = {Journal of Organic Chemistry},
title = {Photochemistry of (Z)-Isovinylneoxanthobilirubic Acid Methyl Ester, a Bilirubin Dipyrrinone Subunit: Femtosecond Transient Absorption and Stimulated Raman Emission Spectroscopy},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.1c02870},
volume = {87},
year = {2022}
}
TY - JOUR
ID - 1863612
AU - Madea, Dominik - Mujawar, Taufiqueahmed Pirsaheb - Dvořák, Aleš - Pospíšilová, Kateřina - Muchová, Lucie - Čubáková, Petra - Kloz, Miroslav - Švenda, Jakub - Vítek, Libor - Klán, Petr
PY - 2022
TI - Photochemistry of (Z)-Isovinylneoxanthobilirubic Acid Methyl Ester, a Bilirubin Dipyrrinone Subunit: Femtosecond Transient Absorption and Stimulated Raman Emission Spectroscopy
JF - Journal of Organic Chemistry
VL - 87
IS - 5
SP - 3089-3103
EP - 3089-3103
PB - American Chemical Society
SN - 00223263
KW - Alcohols
KW - Molecular structure
KW - Photooxidation
KW - Quantum mechanics
KW - Quantum yield
UR - https://pubs.acs.org/doi/10.1021/acs.joc.1c02870
N2 - Bilirubin (BR) is an essential metabolite formed by the catabolism of heme. Phototherapy with blue-green light can be applied to reduce high concentrations of BR in blood and is used especially in the neonatal period. In this work, we studied the photochemistry of (Z)-isovinylneoxanthobilirubic acid methyl ester, a dipyrrinone subunit of BR, by steady-state absorption, femtosecond transient absorption, and stimulated Raman spectroscopies. Both the (Z)- and (E)-configurational isomers of isovinylneoxanthobilirubic acid undergo wavelength-dependent and reversible photoisomerization. The isomerization from the excited singlet state is ultrafast (the lifetimes of (Z)- and (E)-isomers were found to be similar to 0.9 and 0.1 ps, respectively), and its efficiencies increase with increased photon energy. In addition, we studied sensitized photooxidation of the dipyrrinone subunit by singlet oxygen that leads to the formation of propentdyopents. Biological activities of these compounds, namely, effects on the superoxide production, lipoperoxidation, and tricarboxylic acid cycle metabolism, were also studied. Finally, different photochemical and biological properties of this BR subunit and its structural analogue, (Z)-vinylneoxanthobilirubic acid methyl ester, studied before, are discussed.
ER -
MADEA, Dominik, Taufiqueahmed Pirsaheb MUJAWAR, Aleš DVOŘÁK, Kateřina POSPÍŠILOVÁ, Lucie MUCHOVÁ, Petra ČUBÁKOVÁ, Miroslav KLOZ, Jakub ŠVENDA, Libor VÍTEK and Petr KLÁN. Photochemistry of (Z)-Isovinylneoxanthobilirubic Acid Methyl Ester, a Bilirubin Dipyrrinone Subunit: Femtosecond Transient Absorption and Stimulated Raman Emission Spectroscopy. \textit{Journal of Organic Chemistry}. American Chemical Society, 2022, vol.~87, No~5, p.~3089-3103. ISSN~0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.1c02870.
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