Wavelength-Dependent Photochemistry and Biological Relevance of a Bilirubin Dipyrrinone Subunit
The result's identifiers
Result code in 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>
Alternative codes found
RIV/00216224:14310/20:00117255 RIV/00216208:11110/20:10417702 RIV/00064165:_____/20:10417702
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Wavelength-Dependent Photochemistry and Biological Relevance of a Bilirubin Dipyrrinone Subunit
Original language description
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.
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10403 - Physical chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
—
Volume of the periodical
85
Issue of the periodical within the volume
20
Country of publishing house
US - UNITED STATES
Number of pages
14
Pages from-to
13015-13028
UT code for WoS article
000582579900016
EID of the result in the Scopus database
2-s2.0-85094570765