All

What are you looking for?

All
Projects
Results
Organizations

Quick search

  • Projects supported by TA ČR
  • Excellent projects
  • Projects with the highest public support
  • Current projects

Smart search

  • That is how I find a specific +word
  • That is how I leave the -word out of the results
  • “That is how I can find the whole phrase”

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