Wavelength-Dependent Photochemistry and Biological Relevance of
a Bilirubin Dipyrrinone Subunit

J 2020

Wavelength-Dependent Photochemistry and Biological Relevance of a Bilirubin Dipyrrinone Subunit

MADEA, Dominik, Sadegh MAHVIDI, David CHALUPA, Taufiqueahmed Pirsaheb MUJAWAR, Aleš DVOŘÁK et. al.

Základní údaje

Originální název

Wavelength-Dependent Photochemistry and Biological Relevance of a Bilirubin Dipyrrinone Subunit

Autoři

MADEA, Dominik (203 Česká republika, domácí), Sadegh MAHVIDI (364 Írán, domácí), David CHALUPA (203 Česká republika, domácí), Taufiqueahmed Pirsaheb MUJAWAR (356 Indie, domácí), Aleš DVOŘÁK (203 Česká republika), Lucie MUCHOVA (203 Česká republika), Jiří JANOŠ (203 Česká republika), Petr SLAVÍČEK (203 Česká republika), Jakub ŠVENDA (203 Česká republika, domácí), Libor VÍTEK (203 Česká republika) a Petr KLÁN (203 Česká republika, garant, domácí)

Vydání

Journal of Organic Chemistry, Washington, D.C. American Chemical Society, 2020, 0022-3263

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10608 Biochemistry and molecular biology

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.354

Kód RIV

RIV/00216224:14310/20:00117255

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1021/acs.joc.0c01673

UT WoS

000582579900016

Klíčová slova anglicky

Quantum yield; Isomerization; Molecular structure; Quantum mechanics; Irradiation

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 17. 2. 2023 21:04, Mgr. Michaela Hylsová, Ph.D.

Anotace

V originále

Phototherapy is a standard treatment for severe neonatal jaundice to remove toxic bilirubin from the blood. Here, the wavelength-dependent photochemistry of vinylneoxanthobilirubic acid methyl ester, a simplified model of a bilirubin dipyrrinone subunit responsible for a lumirubin-like structural rearrangement, was thoroughly investigated by liquid chromatography and mass and absorption spectroscopies, with the application of a multivariate curve resolution analysis method supplemented with quantum chemical calculations. Irradiation of the model chromophore leads to reversible Z -> E photoisomerization followed by reversible photocyclization to a seven-membered ring system (formed as a mixture of diastereomers). Both the isomerization processes are efficient (Phi(ZE) similar to Phi(EZ) similar to 0.16) when irradiated in the wavelength range of 360-410 nm, whereas the E-isomer cyclization (Phi(c) = 0.006-0.008) and cycloreversion (Phi(-c)= 0.002-0.004) reactions are significantly less efficient. The quantum yields of all processes were found to depend strongly on the wavelength of irradiation, especially when lower energy photons were used. Upon irradiation in the tail of the absorption bands (490 nm), both the isomers exhibit more efficient photoisomerization (Phi(ZE) similar to Phi(EZ )similar to 0.30) and cyclization (Phi(c) = similar to 0.07). In addition, the isomeric bilirubin dipyrrinone subunits were found to possess important antioxidant activities while being substantially less toxic than bilirubin.

Návaznosti

EF16_025/0007381, projekt VaV

Název: Preklinická progrese nových organických sloučenin s cílenou biologickou aktivitou

EF17_043/0009632, projekt VaV

Název: CETOCOEN Excellence

LM2015063, projekt VaV

Název: Národní infrastruktura chemické biologie (Akronym: CZ-OPENSCREEN)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CZ-OPENSCREEN: National Infrastructure for Chemical Biology

LM2018121, projekt VaV

Název: Výzkumná infrastruktura RECETOX (Akronym: RECETOX RI)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, RECETOX RI

NV18-07-00342, projekt VaV

Název: Studium degradačních produktů bilirubinu vznikajících při fototerapii novorozenecké žloutenky

Investor: Ministerstvo zdravotnictví ČR, Studium degradačních produktů bilirubinu vznikajících při fototerapii novorozenecké žloutenky

Citovat

MADEA, Dominik, Sadegh MAHVIDI, David CHALUPA, Taufiqueahmed Pirsaheb MUJAWAR, Aleš DVOŘÁK, Lucie MUCHOVA, Jiří JANOŠ, Petr SLAVÍČEK, Jakub ŠVENDA, Libor VÍTEK a Petr KLÁN. Wavelength-Dependent Photochemistry and Biological Relevance of a Bilirubin Dipyrrinone Subunit. Journal of Organic Chemistry. Washington, D.C.: American Chemical Society, 2020, roč. 85, č. 20, s. 13015-13028. ISSN 0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.0c01673.

@article{1705456,
   author = {Madea, Dominik and Mahvidi, Sadegh and Chalupa, David and Mujawar, Taufiqueahmed Pirsaheb and Dvořák, Aleš and Muchova, Lucie and Janoš, Jiří and Slavíček, Petr and Švenda, Jakub and Vítek, Libor and Klán, Petr},
   article_location = {Washington, D.C.},
   article_number = {20},
   doi = {http://dx.doi.org/10.1021/acs.joc.0c01673},
   keywords = {Quantum yield; Isomerization; Molecular structure; Quantum mechanics; Irradiation},
   language = {eng},
   issn = {0022-3263},
   journal = {Journal of Organic Chemistry},
   title = {Wavelength-Dependent Photochemistry and Biological Relevance of a Bilirubin Dipyrrinone Subunit},
   url = {https://doi.org/10.1021/acs.joc.0c01673},
   volume = {85},
   year = {2020}
}

TY  - JOUR
ID  - 1705456
AU  - Madea, Dominik - Mahvidi, Sadegh - Chalupa, David - Mujawar, Taufiqueahmed Pirsaheb - Dvořák, Aleš - Muchova, Lucie - Janoš, Jiří - Slavíček, Petr - Švenda, Jakub - Vítek, Libor - Klán, Petr
PY  - 2020
TI  - Wavelength-Dependent Photochemistry and Biological Relevance of a Bilirubin Dipyrrinone Subunit
JF  - Journal of Organic Chemistry
VL  - 85
IS  - 20
SP  - 13015-13028
EP  - 13015-13028
PB  - American Chemical Society
SN  - 00223263
KW  - Quantum yield
KW  - Isomerization
KW  - Molecular structure
KW  - Quantum mechanics
KW  - Irradiation
UR  - https://doi.org/10.1021/acs.joc.0c01673
L2  - https://doi.org/10.1021/acs.joc.0c01673
N2  - Phototherapy is a standard treatment for severe neonatal jaundice to remove toxic bilirubin from the blood. Here, the wavelength-dependent photochemistry of vinylneoxanthobilirubic acid methyl ester, a simplified model of a bilirubin dipyrrinone subunit responsible for a lumirubin-like structural rearrangement, was thoroughly investigated by liquid chromatography and mass and absorption spectroscopies, with the application of a multivariate curve resolution analysis method supplemented with quantum chemical calculations. Irradiation of the model chromophore leads to reversible Z -> E photoisomerization followed by reversible photocyclization to a seven-membered ring system (formed as a mixture of diastereomers). Both the isomerization processes are efficient (Phi(ZE) similar to Phi(EZ) similar to 0.16) when irradiated in the wavelength range of 360-410 nm, whereas the E-isomer cyclization (Phi(c) = 0.006-0.008) and cycloreversion (Phi(-c)= 0.002-0.004) reactions are significantly less efficient. The quantum yields of all processes were found to depend strongly on the wavelength of irradiation, especially when lower energy photons were used. Upon irradiation in the tail of the absorption bands (490 nm), both the isomers exhibit more efficient photoisomerization (Phi(ZE) similar to Phi(EZ )similar to 0.30) and cyclization (Phi(c) = similar to 0.07). In addition, the isomeric bilirubin dipyrrinone subunits were found to possess important antioxidant activities while being substantially less toxic than bilirubin.
ER  -

MADEA, Dominik, Sadegh MAHVIDI, David CHALUPA, Taufiqueahmed Pirsaheb MUJAWAR, Aleš DVOŘÁK, Lucie MUCHOVA, Jiří JANOŠ, Petr SLAVÍČEK, Jakub ŠVENDA, Libor VÍTEK a Petr KLÁN. Wavelength-Dependent Photochemistry and Biological Relevance of a Bilirubin Dipyrrinone Subunit. \textit{Journal of Organic Chemistry}. Washington, D.C.: American Chemical Society, 2020, roč.~85, č.~20, s.~13015-13028. ISSN~0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.0c01673.

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