Magnesium tetrapyrazinoporphyrazines: tuning of the pK(a) of red-fluorescent pH indicators
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F19%3A10399462" target="_blank" >RIV/00216208:11160/19:10399462 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=aZF_x.qH28" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=aZF_x.qH28</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c9dt00381a" target="_blank" >10.1039/c9dt00381a</a>
Alternative languages
Result language
angličtina
Original language name
Magnesium tetrapyrazinoporphyrazines: tuning of the pK(a) of red-fluorescent pH indicators
Original language description
Magnesium(ii) tetrapyrazinoporphyrazines (TPyzPzs) are excellent red fluorophores (lambda(F) approximate to 663 nm, Phi(F) approximate to 0.53 in THF). In this work, a series of magnesium(ii) complexes of unsymmetrical TPyzPzs bearing one or two phenol substituents was prepared. Suitable substitutions on the phenolic moiety tuned its pK(a) in the range of 5.5 to 13. Deprotonation of the phenolic group at higher pH induced a strong donor (phenolate) in the macrocycle that led to pH-dependent quenching of the red fluorescence of these indicators. pH sensing was proved in water solutions after the incorporation of TPyzPzs into two delivery systems - microemulsions and liposomes. The latter also serves as a simple model of biomembranes. Finally, a wavelength-ratiometric probe was constructed by the incorporation of a TPyzPz indicator and lipophilic pH-nonsensitive BODIPY dye into liposomes. Synthetic precursors for TPyzPzs, substituted pyrazine-2,3-dicarbonitriles, also represent donor-acceptor systems and the pH-dependent changes in absorption spectra may be easily visible to the naked eye.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
30104 - Pharmacology and pharmacy
Result continuities
Project
<a href="/en/project/EF16_019%2F0000841" target="_blank" >EF16_019/0000841: Efficiency and safety improvement of current drugs and nutraceuticals: advanced methods - new challenges</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Dalton Transactions
ISSN
1477-9226
e-ISSN
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Volume of the periodical
48
Issue of the periodical within the volume
18
Country of publishing house
GB - UNITED KINGDOM
Number of pages
12
Pages from-to
6162-6173
UT code for WoS article
000472449300026
EID of the result in the Scopus database
2-s2.0-85065464507