Dimer-promoted fluorescence quenching of coralyne by binding to anionic polysaccharides

Megyesi, Mónika; Biczók, László; Görner, Helmut

doi:10.1039/b822649k

Cited by 21 publications

(29 citation statements)

References 29 publications

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“…Spectrophotometric measurements provided K D = 1.1×10 5 M −1 for the equilibrium constant of coralyne dimerization in water [16,18]. Due probably to its less extended aromatic structure, EH , which is close to the H D = 60 ± 2 kJ mol 1 value obtained for dimerization in the present work.…”

Section: Thermodynamics Of Dimerizationsupporting

confidence: 84%

“…For example, dimerization brought about 20-fold deceleration of the deactivation from the singlet-excited state for oxacarbocyanines [21], whereas almost 9-fold slowing down was found for a merocyanine dye [22]. The coralyne monomer and dimer had 9.7 and 40.7 ns fluorescence decay times, respectively [18].…”

Section: Effect Of Dimerization On the Fluorescence Characteristicsmentioning

confidence: 98%

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The origin of the dual fluorescence of protonated ellipticine in water

Miskolczy

Biczók

Jablonkai

2016

Chemical Physics Letters

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Absorption and fluorescence spectroscopic measurements, as well as isothermal calorimetric titrations showed that the biexponential decay kinetics of protonated ellipticine (EH + )fluorescence in water originates from dimerization. Due to the high equilibrium constant for the association of two EH + and the intense fluorescence of the dimer, deviation from the exponential emission intensity decay commences below micromolar concentrations. Dimerization must be taken into account when EH + concentration is determined by spectrophotometry, and when EH + binding to substrates are studied. The molar absorption coefficients of the monomer and dimer were determined.

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Section: Thermodynamics Of Dimerizationsupporting

confidence: 84%

Section: Effect Of Dimerization On the Fluorescence Characteristicsmentioning

confidence: 98%

The origin of the dual fluorescence of protonated ellipticine in water

Miskolczy

Biczók

Jablonkai

2016

Chemical Physics Letters

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“…We have demonstrated that the photophysical characteristics of Fla are solvent dependent. 36 The remarkable deuterium isotope effect on  f suggested that hydrogen bonding of the singlet-excited Fla offers an effective pathway for dissipation of excitation energy. The partial inclusion in the CB7 core provides a nonpolar, extremely nonpolarizable microenvironment for the guest 37 and diminishes its interaction with water decelerating thereby radiationless deactivation from the singlet-excited state.…”

Section: Methodsmentioning

confidence: 99%

Kinetics of the reversible inclusion of flavopereirine in cucurbit[7]uril

Miskolczy

Biczók

Jablonkai

2017

Phys. Chem. Chem. Phys.

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The temperature dependence of the kinetics of flavopereirine inclusion in cucurbit[7]uril (CB7) was studied by a stopped-flow method in water. The substantial blue-shift of the emission band and the ∼4-fold fluorescence quantum yield enhancement upon host-guest binding permitted the monitoring of the formation and dissociation of the flavopereirine-CB7 1 : 1 complex in real time. The competitive binding of the 1-adamantylammonium cation with extremely high affinity was exploited to selectively and very accurately determine the kinetic parameters of the exit of flavopereirine from the CB7 cavity. The rate constants of the ingression into and the egression from CB7 were found to be 9.0 × 10 M s and 1.6 s at 298 K, respectively. Both processes had substantial activation enthalpy implying that a steric barrier had to be overcome in the course of the reversible encapsulation. The 31 ± 2 kJ mol activation enthalpy of the entry into CB7 was comparable to the 37 ± 2 kJ mol enthalpy change upon the dissociation of the complex.

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“…There is a slightly better fit with three-exponential, which reveals a long lifetime component of about 30 ns which is in agreement with previous reports on coralyne dimers. 60 …”

Section: Resultsmentioning

confidence: 99%

Unexpected Complex Formation between Coralyne and Cyclic Diadenosine Monophosphate Providing a Simple Fluorescent Turn-on Assay to Detect This Bacterial Second Messenger

et al. 2014

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Cyclic diadenosine monophosphate (c-di-AMP) has emerged as an important dinucleotide that is involved in several processes in bacteria, including cell wall remodeling (and therefore resistance to antibiotics that target bacterial cell wall). Small molecules that target c-di-AMP metabolism enzymes have the potential to be used as antibiotics. Coralyne is known to form strong complexes with polyadenine containing eight or more adenine stretches but not with short polyadenine oligonucleotides. Using a panel of techniques (UV, both steady state fluorescence and fluorescence lifetime measurements, circular dichroism (CD), NMR, and Job plots), we demonstrate that c-di-AMP, which contains only two adenine bases is an exception to this rule and that it can form complexes with coralyne, even at low micromolar concentrations. Interestingly, pApA (the linear analog of c-di-AMP that also contains two adenines) or cyclic diguanylate (c-di-GMP, another nucleotide second messenger in bacteria) did not form any complex with coralyne. Unlike polyadenine, which forms a 2:1 complex with coralyne, c-di-AMP forms a higher order complex with coralyne (≥6:1). Additionally, whereas polyadenine reduces the fluorescence of coralyne when bound, c-di-AMP enhances the fluorescence of coralyne. We use the quenching property of halides to selectively quench the fluorescence of unbound coralyne but not that of coralyne bound to c-di-AMP. Using this simple selective quenching strategy, the assay could be used to monitor the synthesis of c-di-AMP by DisA or the degradation of c-di-AMP by YybT. Apart from the practical utility of this assay for c-di-AMP research, this work also demonstrates that, when administered to cells, intercalators might not only associate with polynucleotides, such as DNA or RNA, but also could associate with cyclic dinucleotides to disrupt or modulate signal transduction processes mediated by these nucleotides.

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Dimer-promoted fluorescence quenching of coralyne by binding to anionic polysaccharides

Cited by 21 publications

References 29 publications

The origin of the dual fluorescence of protonated ellipticine in water

The origin of the dual fluorescence of protonated ellipticine in water

Kinetics of the reversible inclusion of flavopereirine in cucurbit[7]uril

Unexpected Complex Formation between Coralyne and Cyclic Diadenosine Monophosphate Providing a Simple Fluorescent Turn-on Assay to Detect This Bacterial Second Messenger

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