Photochemistry of (Z)-Isovinylneoxanthobilirubic Acid Methyl
Ester, a Bilirubin Dipyrrinone Subunit: Femtosecond Transient
Absorption and Stimulated Raman Emission Spectroscopy

J 2022

Photochemistry of (Z)-Isovinylneoxanthobilirubic Acid Methyl Ester, a Bilirubin Dipyrrinone Subunit: Femtosecond Transient Absorption and Stimulated Raman Emission Spectroscopy

MADEA, Dominik, Taufiqueahmed Pirsaheb MUJAWAR, Aleš DVOŘÁK, Kateřina POSPÍŠILOVÁ, Lucie MUCHOVÁ et. al.

Basic information

Original name

Photochemistry of (Z)-Isovinylneoxanthobilirubic Acid Methyl Ester, a Bilirubin Dipyrrinone Subunit: Femtosecond Transient Absorption and Stimulated Raman Emission Spectroscopy

Authors

MADEA, Dominik (203 Czech Republic, belonging to the institution), Taufiqueahmed Pirsaheb MUJAWAR (356 India, belonging to the institution), Aleš DVOŘÁK, Kateřina POSPÍŠILOVÁ, Lucie MUCHOVÁ, Petra ČUBÁKOVÁ, Miroslav KLOZ, Jakub ŠVENDA (203 Czech Republic, belonging to the institution), Libor VÍTEK and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

Journal of Organic Chemistry, American Chemical Society, 2022, 0022-3263

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 3.600

RIV identification code

RIV/00216224:14310/22:00126178

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acs.joc.1c02870

UT WoS

000773458100083

Keywords in English

Alcohols; Molecular structure; Photooxidation; Quantum mechanics; Quantum yield

Abstract

V originále

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.

Links

EF16_025/0007381, research and development project

Name: Preklinická progrese nových organických sloučenin s cílenou biologickou aktivitou

EF17_043/0009632, research and development project

Name: CETOCOEN Excellence

LM2018121, research and development project

Name: Výzkumná infrastruktura RECETOX (Acronym: RECETOX RI)

Investor: Ministry of Education, Youth and Sports of the CR, RECETOX RI

NV18-07-00342, research and development project

Name: Studium degradačních produktů bilirubinu vznikajících při fototerapii novorozenecké žloutenky

Investor: Ministry of Health of the CR

Citovat

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. 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.

@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.

Detailed Information on Publication Record