PMID- 33153219
OWN - NLM
STAT- MEDLINE
DCOM- 20210401
LR  - 20240330
IS  - 1420-3049 (Electronic)
IS  - 1420-3049 (Linking)
VI  - 25
IP  - 21
DP  - 2020 Nov 3
TI  - Binding Modes of a Phenylpyridinium Styryl Fluorescent Dye with Cucurbiturils.
LID - 10.3390/molecules25215111 [doi]
LID - 5111
AB  - In order to explore how cucurbituril hosts accommodate an N-phenyl-pyridinium 
      derivative guest, the complexation of the solvatochromic dye, 
      4-(4-(dimethylamino)styryl)-1-phenylpyridinium iodide (PhSt) with 
      ,',delta,delta'-tetramethyl-cucurbit[6]uril (Me(4)CB6) and cucurbit[7]uril (CB7) was 
      investigated by absorption spectroscopic, fluorescence and NMR experiments. In 
      aqueous solutions, PhSt forms 1:1 complexes with both cucurbiturils, the complex 
      with CB7 has a higher stability constant (K(a) = 6.0 x 10(6) M(-)(1)) than the 
      complex with Me(4)CB6 (K(a) = 1.1 x 10(6) M(-)(1)). As revealed by NMR 
      experiments and confirmed by theoretical calculations, CB7 encapsulates the whole 
      phenylpyridinium entity of the PhSt cation guest, whereas the cavity of Me(4)CB6 
      includes only the phenyl ring, the pyridinium ring is bound to the carbonyl rim 
      of the host. The binding of PhSt to cucurbiturils is accompanied by a strong 
      enhancement of the fluorescence quantum yield due to the blocking of the 
      deactivation through a twisted intramolecular charge transfer (TICT) state. The 
      TICT mechanism in PhSt was characterized by fluorescence experiments in 
      polyethylene glycol (PEG) solvents of different viscosities. The PhSt-CB7 system 
      was tested as a fluorescence indicator displacement (FID) assay, and it 
      recognized trimethyl-lysine selectively over other lysine derivatives.
FAU - Paudics, Adrien
AU  - Paudics A
AD  - Department of Physical Chemistry and Materials Science, Budapest University of 
      Technology and Economics, 1521 Budapest, Hungary.
FAU - Hessz, Dora
AU  - Hessz D
AD  - Department of Physical Chemistry and Materials Science, Budapest University of 
      Technology and Economics, 1521 Budapest, Hungary.
FAU - Bojtar, Marton
AU  - Bojtar M
AD  - "Lendulet" Chemical Biology Research Group, Institute of Organic Chemistry, 
      Research Centre for Natural Sciences, 1519 Budapest, Hungary.
FAU - Gyarmati, Benjamin
AU  - Gyarmati B
AD  - Department of Physical Chemistry and Materials Science, Budapest University of 
      Technology and Economics, 1521 Budapest, Hungary.
FAU - Szilagyi, Andras
AU  - Szilagyi A
AD  - Department of Physical Chemistry and Materials Science, Budapest University of 
      Technology and Economics, 1521 Budapest, Hungary.
FAU - Kallay, Mihaly
AU  - Kallay M
AD  - Department of Physical Chemistry and Materials Science, Budapest University of 
      Technology and Economics, 1521 Budapest, Hungary.
FAU - Bitter, Istvan
AU  - Bitter I
AD  - Department of Organic Chemistry and Technology, Budapest University of Technology 
      and Economics, 1521 Budapest, Hungary.
FAU - Kubinyi, Miklos
AU  - Kubinyi M
AD  - Department of Physical Chemistry and Materials Science, Budapest University of 
      Technology and Economics, 1521 Budapest, Hungary.
LA  - eng
GR  - FK 125074 and KKP 126451/National Research, Development and Innovation Office, 
      Hungary/
GR  - UNKP-19-3/New National Excellence Program of the Ministry of Innovation and 
      Technology, Hungary/
GR  - BME FIKP-BIO/Higher Education Excellence Program of the Ministry of Human 
      Capacities, Hungary/
PT  - Journal Article
DEP - 20201103
PL  - Switzerland
TA  - Molecules
JT  - Molecules (Basel, Switzerland)
JID - 100964009
RN  - 0 (Fluorescent Dyes)
RN  - 0 (Macrocyclic Compounds)
RN  - 0 (Pyridines)
RN  - 0 (cucurbit(n)uril)
SB  - IM
MH  - Fluorescent Dyes/*chemistry
MH  - Macrocyclic Compounds/*chemistry
MH  - *Models, Molecular
MH  - Pyridines/*chemistry
MH  - Spectrometry, Fluorescence
PMC - PMC7663148
OTO - NOTNLM
OT  - host-guest complex
OT  - hydrophobic interactions
OT  - molecular recognition
OT  - size selectivity
COIS- The authors declare no conflict of interest. The funders had no role in the 
      design of the study; in the collection, analyses, or interpretation of data; in 
      the writing of the manuscript, or in the decision to publish the results.
EDAT- 2020/11/07 06:00
MHDA- 2021/04/02 06:00
PMCR- 2020/11/03
CRDT- 2020/11/06 01:02
PHST- 2020/09/25 00:00 [received]
PHST- 2020/10/27 00:00 [revised]
PHST- 2020/10/29 00:00 [accepted]
PHST- 2020/11/06 01:02 [entrez]
PHST- 2020/11/07 06:00 [pubmed]
PHST- 2021/04/02 06:00 [medline]
PHST- 2020/11/03 00:00 [pmc-release]
AID - molecules25215111 [pii]
AID - molecules-25-05111 [pii]
AID - 10.3390/molecules25215111 [doi]
PST - epublish
SO  - Molecules. 2020 Nov 3;25(21):5111. doi: 10.3390/molecules25215111.