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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F20%3A43920927" target="_blank" >RIV/60461373:22340/20:43920927 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216224:14310/20:00117255 RIV/00216208:11110/20:10417702 RIV/00064165:_____/20:10417702

Výsledek na webu

<a href="https://pubs.acs.org/doi/abs/10.1021/acs.joc.0c01673" target="_blank" >https://pubs.acs.org/doi/abs/10.1021/acs.joc.0c01673</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.joc.0c01673" target="_blank" >10.1021/acs.joc.0c01673</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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 (φZE ∼φEZ ∼0.16) when irradiated in the wavelength range of 360-410 nm, whereas the E-isomer cyclization (φc = 0.006-0.008) and cycloreversion (φ-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 (φZE ∼φEZ ∼0.30) and cyclization (φc = ∼0.07). In addition, the isomeric bilirubin dipyrrinone subunits were found to possess important antioxidant activities while being substantially less toxic than bilirubin. © 2020 American Chemical Society.

Název v anglickém jazyce

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

Popis výsledku anglicky

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 (φZE ∼φEZ ∼0.16) when irradiated in the wavelength range of 360-410 nm, whereas the E-isomer cyclization (φc = 0.006-0.008) and cycloreversion (φ-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 (φZE ∼φEZ ∼0.30) and cyclization (φc = ∼0.07). In addition, the isomeric bilirubin dipyrrinone subunits were found to possess important antioxidant activities while being substantially less toxic than bilirubin. © 2020 American Chemical Society.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2020

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

—

Svazek periodika

85

Číslo periodika v rámci svazku

20

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

14

Strana od-do

13015-13028

Kód UT WoS článku

000582579900016

EID výsledku v databázi Scopus

2-s2.0-85094570765