Coumarin–nucleotide base pairs. Ultraviolet absorption, fluorescence, and photochemical study

Wenska, G.; Paszỳc, S.

doi:10.1139/v84-342

Cited by 9 publications

(6 citation statements)

References 14 publications

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“…The degree of stacking interaction CouO-C3-Ade > CouO-C3-Thy -CouO-C3-Ura, obtained here from fluorescence measurements, is in agreement with that obtained from uv absorption (hypochromism) (5). Similar results were obtained for nucleotide base -psoralen pairs.…”

Section: E Osupporting

confidence: 89%

Ground and excited-state interactions of coumarin and nucleotide base

Wenska¹,

Paszỳc²

1988

Can. J. Chem.

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GRAZYNA WENSKA and STEFAN PASZYC. Can. J . Chem. 66, 5 13 (1988).Steady-state and time-resolved fluorescence measurements for a series of bichromophoric con~pounds containing 7-methoxycoumarin and nucleotide base residues have been performed in water and in organic solvents. The data from these studies have been used to calculate the relative proportion of folded and extended conformations of bichromophores. Ground-state stacking interactions of coumarin and nucleotide base have been found to be limited to aqueous solution. ' The contribution of the dynamic quenching mechanism to the total fluorescence quenching in water has been estimated. The absence of dynamic quenching in organic solvents isexplained on the basis of the very short lifetime of the fluorophore in methanol.GRAZYNA WENSKA et STEFAN PASZYC. Can. J. Chem. 66, 513 (1988).Operant dans I'eau et dans des solvants organiques, on a mesurC la fluorescence a I'Ctat stationnaire ainsi que celle rCsolue en fonction du temps d'une sCrie de composCs bichromophoriques contenant des rtsidus mCthoxy-7 coumarine et une base nuclCotide. On a utilisC les donntes ainsi obtenues pour calculer les proportions relatives des conformations replite et Ctendue des bichromophores. On a trouve que les interactions d'empilement dans 1'Ctat fondamental de la coumarine et de la base nuclCotide sont IimitCes aux solutions aqueuses. On a t v a l d la contribution du mecanisme de piegeage dynamique au pitgeage total de la fluorescence dans I'eau. On explique l'absence de pitgeage dynamique dans les solvants organiques par le temps de vie tres court du fluorophore dans le methanol.[Traduit par la revue] Introduction It is well known that heteroaromatic compounds from the psoralen family form noncovalent complexes with nucleic acids (1, 2). The formation of the complex by weak forces, i.e., aromatic ring stacking due to hydrophobic and van der Waals forces, is one of several parameters contributing to the overall photobiological activity of psoralens (furocoumarins). The complexation is usually described in terms of the "intercalation model", which predicts that the psoralen molecule is placed between two adjacent nucleotide base pairs. Both ultraviolet absorption and fluorescence spectroscopy can be used to detect the intercalation complex. Its formation is generally accompanied by the bathochromic shift and hypochromicity of the near ultraviolet (uv) absorption band of the psoralen derivative. The fluorescence properties of psoralens also vary upon intercalation. The ability of nucleic acid bases to form such complexes with psoralen has been tested using model compounds in which both interacting molecules were connected with a hydrocarbon chain. The percentage of stacked or folded conformation, as opposed to extended, was determined by the study of the variation of the hypochromic effect with temperature (3, 4).Recently we synthesized a series of compounds containing 7-methoxycoumarin and nucleic acid base: adenine, thymine, and uracil, linked together with a polymethylene chain. ...

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Section: E Osupporting

confidence: 89%

Ground and excited-state interactions of coumarin and nucleotide base

Wenska¹,

Paszỳc²

1988

Can. J. Chem.

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“…In acetonitrile, the absorption spectra of PDC–fluorophore conjugates (Figure ) resemble the arithmetical sum of the spectra of the corresponding model compounds, that is, PDC‐L and C m ‐L (or PY‐L ). However, we observed a small decrease of the intensity of the long‐wavelength absorption band of the conjugates with respect to the sum of absorption of model compounds (hypochromic effect), indicative of intramolecular interactions between PDC and fluorophore moieties . This effect is quantitatively expressed by percent hypochromism H ( PDC‐L2‐C3 : H =18 %, other conjugates: H <10 % in acetonitrile, Table ).…”

Section: Resultsmentioning

confidence: 82%

“…However,w eo bserved as mall decrease of the intensity of the long-wavelengtha bsorption band of the conjugatesw ith respect to the sum of absorption of model compounds (hypochromic effect), indicative of intramolecular interactions between PDC and fluorophore moieties. [53][54][55] This effect is quantitativelye xpressedb yp ercenth ypochromism H (PDC-L2-C3: H = 18 %, other conjugates: H < 10 %i na cetonitrile, Ta ble 1). In aqueous buffer solution,t he hypochromic effect was much more pronounced( up to H % 40 %f or PDC-L1-C2 and PDC-L2-C3), giving evidence of significantly more efficient intramolecular stacking interactions.…”

Section: Absorption Spectramentioning

confidence: 99%

Topology‐Selective, Fluorescent “Light‐Up” Probes for G‐Quadruplex DNA Based on Photoinduced Electron Transfer

Xie

Reznichenko

Chaput

et al. 2018

Chemistry A European J

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Six novel probes were prepared by covalent attachment of a G4-DNA ligand (bis(quinolinium) pyridodicarboxamide; PDC) to various coumarin or pyrene fluorophores. In the absence of DNA, the fluorescence of all probes is quenched due to intramolecular photoinduced electron transfer (PET), as evidenced by photophysical and electrochemical studies, molecular modeling, and DFT calculations. All probes demonstrate similarly high thermal stabilization of various G4-DNA substrates belonging to different folding topologies, as assessed by fluorescence melting experiments; however, their fluorimetric response is strongly heterogeneous with respect to the structures of the probes and G4-DNA targets. Thus, the probes containing the 7-diethylaminocoumarin fluorophore demonstrate significant fluorescence enhancement in the presence of G4-DNA, with the strongest "light-up" response (20- to 180-fold) observed for antiparallel G4 structures as well as for hybrid G4 structures, formed by the variants of human telomeric sequence and capable of a conformation change to the antiparallel isoform. These results shed light on the influence of the linker and electronic properties of fluorophores on the efficiency of G4-DNA "light-up" probes operating via PET.

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“…The coordination of phosphate anion to Cu 2+ ion weakens the bond between the phenol oxygen atom and Cu 2+ ion [ 35 ]. In addition, it is known that adenine interacts with aromatic compounds, including coumarin derivatives [ 36 , 37 ]. Both coordination and interaction are considered to change the characteristics of the electronic state on the coumarin moiety, which results in a specific absorbance change.…”

Section: Resultsmentioning

confidence: 99%

Development of Dipicolylamine-Modified Cyclodextrins for the Design of Selective Guest-Responsive Receptors for ATP

et al. 2018

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The construction of supramolecular recognition systems based on specific host–guest interactions has been studied in order to design selective chemical sensors. In this study, guest-responsive receptors for ATP have been designed with cyclodextrins (CyDs) as a basic prototype of the turn-on type fluorescent indicator. We synthesized dipicolylamine (DPA)-modified CyD–Cu2+ complexes (Cu·1α, Cu·1β, and Cu·1γ), and evaluated their recognition capabilities toward phosphoric acid derivatives in water. The UV-Vis absorption and fluorescence spectra revealed that Cu·1β selectively recognized ATP over other organic and inorganic phosphates, and that β-CyD had the most suitable cavity size for complexation with ATP. The 1D and 2D NMR analyses suggested that the ATP recognition was based on the host–guest interaction between the adenine moiety of ATP and the CyD cavity, as well as the recognition of phosphoric moieties by the Cu2+–DPA complex site. The specific interactions between the CyD cavity and the nucleobases enabled us to distinguish ATP from other nucleoside triphosphates, such as guanosine triphosphate (GTP), uridine triphosphate (UTP), and cytidine triphosphate (CTP). This study clarified the basic mechanisms of molecular recognition by modified CyDs, and suggested the potential for further application of CyDs in the design of highly selective supramolecular recognition systems for certain molecular targets in water.

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Coumarin–nucleotide base pairs. Ultraviolet absorption, fluorescence, and photochemical study

Cited by 9 publications

References 14 publications

Ground and excited-state interactions of coumarin and nucleotide base

Ground and excited-state interactions of coumarin and nucleotide base

Topology‐Selective, Fluorescent “Light‐Up” Probes for G‐Quadruplex DNA Based on Photoinduced Electron Transfer

Development of Dipicolylamine-Modified Cyclodextrins for the Design of Selective Guest-Responsive Receptors for ATP

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