On the interaction of caffeine with nucleic acids

Fritzsche, H.; Petri, I.; Schütz, H.; Weller, K.; Sedmera, Petr; Lang, H.

doi:10.1016/0301-4622(80)85013-7

Cited by 53 publications

(11 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…4 allowed us to bracket the value of K, as 27 + 10 L mol-'. This value agrees reasonably well with the value of 18.1 L mol-' derived from ultraviolet spectra (19,20). In addition, an analysis of the dependence of peak position of bands 1 and 2 with caffeine concentration (Table 1) yielded independent estimates of the polymer fraction, F,, consistent with K, = 158 L mol-' and K, = 27 L mol-'.…”

Section: Absence Of Isosbestic Pointssupporting

confidence: 86%

“…At higher caffeine concentrations, trimers and higher polymers are also present and the isodesmic model (1,17,18) has been used to calculate an apparent single association constant, K, from various physico-chemical measurements (19)(20)(21)(22)(23)(24). el, identical with the one described here, was used by Iza et al (15,16) to obtain the values Kd = 158.1 L mol-' and K, = 18.1 L mol-' from the ultraviolet spectra of caffeine in the concentration range 1 X to 5 X M. We have adopted their value of Kd derived from ultraviolet data as the best available, but for K, we have used a value estimated from the results of Fourier deconvolution of the infrared spectra, as explained below.…”

Section: Absence Of Isosbestic Pointsmentioning

confidence: 99%

See 1 more Smart Citation

Self-association of caffeine in aqueous solution: an FT-IR study

Falk¹,

Gil²,

Iza³

1990

Can. J. Chem.

View full text Add to dashboard Cite

MICHAEL FALK, MANUEL GIL, and NEREA IZA. Can. J. Chem. 68, 1293 (1990). Spectra of caffeine in DzO solution (0.003 to 0.129 M) were studied by Fourier-transform infrared spectroscopy. Spectral changes in the carbonyl stretching region were interpreted in terms of the self-association equilibria resulting from the stacking of caffeine molecules. Absence of isosbestic points indicated the occurrence of more than two spectroscopically distinct caffeine species. A simple monomer-dimer-polymer model was employed, in which the successive equilibria are governed by two association constants, Kd for the formation of dimers and K, for the formation of trimers and larger polymers. The value Kd = 158.1 L mol-I was taken from a recent ultraviolet study by Iza et al. and the value K, = 27 L mol-' was derived from the analysis of infrared band profiles sharpened by Fourier self-deconvolution. From these values of Kd and K,, the weight fractions of monomers, dimers, and polymers were calculated for every caffeine concentration and their individual molar absorptivity spectra were derived. In agreement with the earlier work of Maevsky and Sukhorukov, it was found that stacking association causes shifts of both C=O stretching fundamentals to higher wavenumbers. The monomer-dimer shifts are smaller than the dimerpolymer shifts. Analogous shifts were observed for the stacking self-association of 1,3-dimethyluracil in D 2 0 . The shifts to higher wavenumbers are probably caused by the diminished hydrogen bonding of water to C=O groups of the stacked bases.Key words: caffeine, self association, infrared spectroscopy, base stacking.MICHAEL FALK, MANUEL GIL et NEREA IZA. Can. J. Chem. 68, 1293 (1990). Nous avons CtudiC les spectres de la cafkine dans des solutions de D 2 0 (0.003 ? I 0.129 M) par la spectroscopie infrarouge 5 transformke de Fourier. La variation des spectres dans la region de vibration de valence des groupes C=O a Ctk interpret6 en termes des Cquilibres impliquant l'auto-association par empilage de molkcules de cafkine. L'absence de points isosbestiques a indiquC l'existence d'au moins trois espkces distinctes de cafkine. Nous avons employ6 un modkle monomkre-dimkrepolymkre, dans lequel les Cquilibres successifs sont controlks par deux constantes d'association, Kd pour la dimkrization et K , pour la formation de trimkres et de polymkres plus grands. La valeur Kd = 158.1 L mol-I a CtC prise de 1'Ctude rCcente faite par Iza et al., tandis que la valeur K, = 27 L mol-' a CtC derivke de l'analyse des profiles de bandes infrarouges obtenues par auto-dCconvolution. A partir des valeurs de Kd et K,, nous avons calculk la fraction en poids des monomkres, dimkres et polymkres pour chaque concentration de cafCine, ce qui nous a permis de calculer leurs spectres individuels. En accord avec les travaux antCrieurs de Maevsky et Sukhorukov, nous avons trouvC que l'association par empilage cause des dCplacements de vibrations de valence des groupes C=O vers les hautes frkquences. Les dkplacements monomkre-dimkre sont moins grands que...

show abstract

Section: Absence Of Isosbestic Pointssupporting

confidence: 86%

Section: Absence Of Isosbestic Pointsmentioning

confidence: 99%

Self-association of caffeine in aqueous solution: an FT-IR study

Falk¹,

Gil²,

Iza³

1990

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

“…It is important to note that a typical distance, d = 0.34 nm, between the chromophores of the drug and mononucleotide in the 1:1 complex comes from X-ray diffraction analysis [112]. Similar results were later obtained for the antibiotics daunomycin [113] and doxorubicin [33], xanthines [111,[114][115][116], psychotomimetic drugs [69], quinolones [117], polyphenols [118], and other aromatic drugs. It was shown that hetero-association is enhanced by the presence of divalent metal ions due to interaction of the drug with nucleoside phosphates via the ion, as demonstrated for the fluoroquinolone antibiotics [117].…”

Section: Hetero-association Of Aromatic Drugs With Derivatives Of Nucsupporting

confidence: 52%

“…Conclusions about the predominant location of the chromophore of the base above the chromophore of the ligand were made from the calculated values of the induced proton and carbon NMR chemical shifts of the bases. In some cases, the approximate orientation of the base with respect to the antibiotic in 1:1 complex was estimated on the basis of comparison between experimental and theoretically calculated proton magnetic shielding [69,111]. In the majority of cases, stacking between the ligand and mononucleotides obtained in aqueous solution is in line with crystallographic studies [106].…”

Section: Hetero-association Of Aromatic Drugs With Derivatives Of Nucmentioning

confidence: 63%

“…the magnitudes of the hetero-association parameters are intermediate between the corresponding self-association parameters of the interacting molecules and the values of ΔH h and ΔS h [33,111] are both negative. It was realised, however, that the average magnitudes of K h and ΔH h are higher in absolute value than those for the hetero-association of the derivatives of nucleic acid bases, which was suggested to be due to a more extended aromatic system of the drug (typically 2-4 aromatic rings in the chromophore) [33,69].…”

Section: Hetero-association Of Aromatic Drugs With Derivatives Of Nucmentioning

confidence: 99%

See 1 more Smart Citation

Hetero-association of aromatic molecules in aqueous solution

Evstigneev

2014

International Reviews in Physical Chemistry

View full text Add to dashboard Cite

Knowledge of the physical chemistry of small molecules complexation (the hetero-association) in aqueous solution is increasingly important in view of the rapidly emerging branch of supramolecular chemistry dealing with the formation of heterogeneous polymeric structures having specific functional roles. In this paper, the 50-year history of scientific studies of hetero-association of heterocyclic aromatic molecules in aqueous solution has been reviewed. Some important correlations of structural and thermodynamic parameters of complexation have been reported based on large data-set of hetero-association parameters accumulated to date. The fundamental problem of 'energetic composition' of π-stacking is extensively discussed. The review has shown that there are some gaps in our understanding of heteroassociation, which provides a challenge for further studies in this area.

show abstract

The Spectra of Purines ( H 507)

1996

Chemistry of Heterocyclic Compounds: A Series of Monographs

View full text Add to dashboard Cite

On the interaction of caffeine with nucleic acids

Cited by 53 publications

References 34 publications

Self-association of caffeine in aqueous solution: an FT-IR study

Self-association of caffeine in aqueous solution: an FT-IR study

Hetero-association of aromatic molecules in aqueous solution

The Spectra of Purines ( H 507)

Contact Info

Product

Resources

About