Photosensitized Cross-Linking of Tryptophan and Tyrosine
Derivatives by Rose Bengal in Aqueous Solutions

J 2018

Photosensitized Cross-Linking of Tryptophan and Tyrosine Derivatives by Rose Bengal in Aqueous Solutions

LUDVÍKOVÁ, Lucie, Peter ŠTACKO, Jonathan SPERRY a Petr KLÁN

Základní údaje

Originální název

Photosensitized Cross-Linking of Tryptophan and Tyrosine Derivatives by Rose Bengal in Aqueous Solutions

Autoři

LUDVÍKOVÁ, Lucie (203 Česká republika, domácí), Peter ŠTACKO (703 Slovensko, domácí), Jonathan SPERRY (554 Nový Zéland) a Petr KLÁN (203 Česká republika, garant, domácí)

Vydání

Journal of Organic Chemistry, WASHINGTON, AMER CHEMICAL SOC, 2018, 0022-3263

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.745

Kód RIV

RIV/00216224:14310/18:00105663

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1021/acs.joc.8b01545

UT WoS

000445713000015

Klíčová slova anglicky

LASER FLASH-PHOTOLYSIS; AROMATIC-AMINO-ACIDS; EXCITED-STATE CHEMISTRY; SINGLET OXYGEN; SENSITIZED PHOTOOXIDATION; MEMBRANE-PROTEINS; OXIDATION; PEPTIDES; RESIDUES; SKIN

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 18. 1. 2019 15:57, Mgr. Michaela Hylsová, Ph.D.

Anotace

V originále

Photosensitized cross-linking of N-acetyl derivatives of tryptophan and tyrosine by rose bengal in phosphate buffer saline was studied by steady-state absorption and emission spectroscopy, nanosecond transient absorption spectroscopy, and chemical analyses. These amino acids undergo cross-linking to form dimeric and higher oligomeric products under anoxic conditions with rose bengal as a sacrificial oxidant, whereas they react predominantly with singlet oxygen produced by rose bengal in aerated solutions. This investigation provides a comprehensive view into the first steps of rose bengal photosensitized cross-linking of these two amino acids. The results can be helpful for future applications of rose bengal and related dyes, such as photochemical tissue bonding or visible light photocatalysis.

Návaznosti

LO1214, projekt VaV

Název: Centrum pro výzkum toxických látek v prostředí (Akronym: RECETOX)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Centrum pro výzkum toxických látek v prostředí

NV18-07-00342, interní kód MU

Název: Studium degradačních produktů bilirubinu vznikajících při fototerapii novorozenecké žloutenky

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

Citovat

LUDVÍKOVÁ, Lucie, Peter ŠTACKO, Jonathan SPERRY a Petr KLÁN. Photosensitized Cross-Linking of Tryptophan and Tyrosine Derivatives by Rose Bengal in Aqueous Solutions. Journal of Organic Chemistry. WASHINGTON: AMER CHEMICAL SOC, 2018, roč. 83, č. 18, s. 10835-10844. ISSN 0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.8b01545.

@article{1488106,
   author = {Ludvíková, Lucie and Štacko, Peter and Sperry, Jonathan and Klán, Petr},
   article_location = {WASHINGTON},
   article_number = {18},
   doi = {http://dx.doi.org/10.1021/acs.joc.8b01545},
   keywords = {LASER FLASH-PHOTOLYSIS; AROMATIC-AMINO-ACIDS; EXCITED-STATE CHEMISTRY; SINGLET OXYGEN; SENSITIZED PHOTOOXIDATION; MEMBRANE-PROTEINS; OXIDATION; PEPTIDES; RESIDUES; SKIN},
   language = {eng},
   issn = {0022-3263},
   journal = {Journal of Organic Chemistry},
   title = {Photosensitized Cross-Linking of Tryptophan and Tyrosine Derivatives by Rose Bengal in Aqueous Solutions},
   url = {https://pubs.acs.org/doi/10.1021/acs.joc.8b01545},
   volume = {83},
   year = {2018}
}

TY  - JOUR
ID  - 1488106
AU  - Ludvíková, Lucie - Štacko, Peter - Sperry, Jonathan - Klán, Petr
PY  - 2018
TI  - Photosensitized Cross-Linking of Tryptophan and Tyrosine Derivatives by Rose Bengal in Aqueous Solutions
JF  - Journal of Organic Chemistry
VL  - 83
IS  - 18
SP  - 10835-10844
EP  - 10835-10844
PB  - AMER CHEMICAL SOC
SN  - 00223263
KW  - LASER FLASH-PHOTOLYSIS
KW  - AROMATIC-AMINO-ACIDS
KW  - EXCITED-STATE CHEMISTRY
KW  - SINGLET OXYGEN
KW  - SENSITIZED PHOTOOXIDATION
KW  - MEMBRANE-PROTEINS
KW  - OXIDATION
KW  - PEPTIDES
KW  - RESIDUES
KW  - SKIN
UR  - https://pubs.acs.org/doi/10.1021/acs.joc.8b01545
L2  - https://pubs.acs.org/doi/10.1021/acs.joc.8b01545
N2  - Photosensitized cross-linking of N-acetyl derivatives of tryptophan and tyrosine by rose bengal in phosphate buffer saline was studied by steady-state absorption and emission spectroscopy, nanosecond transient absorption spectroscopy, and chemical analyses. These amino acids undergo cross-linking to form dimeric and higher oligomeric products under anoxic conditions with rose bengal as a sacrificial oxidant, whereas they react predominantly with singlet oxygen produced by rose bengal in aerated solutions. This investigation provides a comprehensive view into the first steps of rose bengal photosensitized cross-linking of these two amino acids. The results can be helpful for future applications of rose bengal and related dyes, such as photochemical tissue bonding or visible light photocatalysis.
ER  -

LUDVÍKOVÁ, Lucie, Peter ŠTACKO, Jonathan SPERRY a Petr KLÁN. Photosensitized Cross-Linking of Tryptophan and Tyrosine Derivatives by Rose Bengal in Aqueous Solutions. \textit{Journal of Organic Chemistry}. WASHINGTON: AMER CHEMICAL SOC, 2018, roč.~83, č.~18, s.~10835-10844. ISSN~0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.8b01545.

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