Influence of Solvent Polarity and DNA-Binding on Spectral
Properties of Quaternary Benzo[c]phenanthridine Alkaloids

J 2015

Influence of Solvent Polarity and DNA-Binding on Spectral Properties of Quaternary Benzo[c]phenanthridine Alkaloids

RÁJECKÝ, Michal; Kristýna ŠEBRLOVÁ; Filip MRAVEC a Petr TÁBORSKÝ

Základní údaje

Originální název

Influence of Solvent Polarity and DNA-Binding on Spectral Properties of Quaternary Benzo[c]phenanthridine Alkaloids

Název česky

Vliv polarity rozpouštědla a vazby DNA na spektrální vlastnosti kvartérních benzo[c]fenanthridinových alkaloidů

Autoři

RÁJECKÝ, Michal ; Kristýna ŠEBRLOVÁ; Filip MRAVEC a Petr TÁBORSKÝ

Vydání

Plos one, San Francisco, Public Library of Science, 2015, 1932-6203

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10406 Analytical chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.057

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/15:00084189

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

benzophenanthridine alkaloids;isoquinoline alkaloids;pseudobase formation;small molecules;sanguinarine;chelerythrine;sanguilutine;sanguirubine;chelirubine;macarpine;fluorescence;dna

Štítky

AKR, EL OK, podil, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 8. 2. 2018 10:57, doc. Mgr. Petr Táborský, Ph.D.

Anotace

V originále

Quaternary benzo[c]phenanthridine alkaloids are secondary metabolites of the plant families Papaveraceae, Rutaceae, and Ranunculaceae with anti-inflammatory, antifungal, antimicrobial and anticancer activities. Their spectral changes induced by the environment could be used to understand their interaction with biomolecules as well as for analytical purposes. Spectral shifts, quantum yield and changes in lifetime are presented for the free form of alkaloids in solvents of different polarity and for alkaloids bound to DNA. Quantum yields range from 0.098 to 0.345 for the alkanolamine form and are below 0.033 for the iminium form. Rise of fluorescence lifetimes (from 2-5 ns to 3-10 ns) and fluorescence intensity are observed after binding of the iminium form to the DNA for most studied alkaloids. The alkanolamine form does not bind to DNA. Acid-base equilibrium constant of macarpine is determined to be 8.2-8.3. Macarpine is found to have the highest increase of fluorescence upon DNA binding, even under unfavourable pH conditions. This is probably a result of its unique methoxy substitution at C-12 a characteristic not shared with other studied alkaloids. Association constant for macarpine-DNA interaction is 700000 M-1.

Návaznosti

LH12176, projekt VaV

Název: Benzofenanthridinové alkaloidy - studium účinků na celulární a molekulární úrovni (Akronym: KBF)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Benzofenathridinové alkaloidy-studium účinků na celulární a molekulární úrovni

Citovat

RÁJECKÝ, Michal; Kristýna ŠEBRLOVÁ; Filip MRAVEC a Petr TÁBORSKÝ. Influence of Solvent Polarity and DNA-Binding on Spectral Properties of Quaternary Benzo[c]phenanthridine Alkaloids. Plos one. San Francisco: Public Library of Science, 2015, roč. 10, č. 6, s. "nestránkováno", 16 s. ISSN 1932-6203. Dostupné z: https://doi.org/10.1371/journal.pone.0129925.

@article{1313333,
   author = {Rájecký, Michal and Šebrlová, Kristýna and Mravec, Filip and Táborský, Petr},
   article_location = {San Francisco},
   article_number = {6},
   doi = {https://doi.org/10.1371/journal.pone.0129925},
   keywords = {benzophenanthridine alkaloids;isoquinoline alkaloids;pseudobase formation;small molecules;sanguinarine;chelerythrine;sanguilutine;sanguirubine;chelirubine;macarpine;fluorescence;dna},
   language = {eng},
   issn = {1932-6203},
   journal = {Plos one},
   title = {Influence of Solvent Polarity and DNA-Binding on Spectral Properties of Quaternary Benzo[c]phenanthridine Alkaloids},
   url = {http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0129925},
   volume = {10},
   year = {2015}
}

TY  - JOUR
ID  - 1313333
AU  - Rájecký, Michal - Šebrlová, Kristýna - Mravec, Filip - Táborský, Petr
PY  - 2015
TI  - Influence of Solvent Polarity and DNA-Binding on Spectral Properties of Quaternary Benzo[c]phenanthridine Alkaloids
JF  - Plos one
VL  - 10
IS  - 6
SP  - "nestránkováno"
EP  - "nestránkováno"
PB  - Public Library of Science
SN  - 19326203
KW  - benzophenanthridine alkaloids;isoquinoline alkaloids;pseudobase formation;small molecules;sanguinarine;chelerythrine;sanguilutine;sanguirubine;chelirubine;macarpine;fluorescence;dna
UR  - http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0129925
L2  - http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0129925
N2  - Quaternary benzo[c]phenanthridine alkaloids are secondary metabolites of the plant families Papaveraceae, Rutaceae, and Ranunculaceae with anti-inflammatory, antifungal, antimicrobial and anticancer activities. Their spectral changes induced by the environment could be used to understand their interaction with biomolecules as well as for analytical purposes. Spectral shifts, quantum yield and changes in lifetime are presented for the free form of alkaloids in solvents of different polarity and for alkaloids bound to DNA. Quantum yields range from 0.098 to 0.345 for the alkanolamine form and are below 0.033 for the iminium form. Rise of fluorescence lifetimes (from 2-5 ns to 3-10 ns) and fluorescence intensity are observed after binding of the iminium form to the DNA for most studied alkaloids. The alkanolamine form does not bind to DNA. Acid-base equilibrium constant of macarpine is determined to be 8.2-8.3. Macarpine is found to have the highest increase of fluorescence upon DNA binding, even under unfavourable pH conditions. This is probably a result of its unique methoxy substitution at C-12 a characteristic not shared with other studied alkaloids. Association constant for macarpine-DNA interaction is 700000 M-1.
ER  -

RÁJECKÝ, Michal; Kristýna ŠEBRLOVÁ; Filip MRAVEC a Petr TÁBORSKÝ. Influence of Solvent Polarity and DNA-Binding on Spectral Properties of Quaternary Benzo[c]phenanthridine Alkaloids. \textit{Plos one}. San Francisco: Public Library of Science, 2015, roč.~10, č.~6, s.~''nestránkováno'', 16 s. ISSN~1932-6203. Dostupné z: https://doi.org/10.1371/journal.pone.0129925.

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