Polyelectrolyte Effects on 9-Aminoacridine-DNA Binding

Friedman, Richard A.; Shahin, Mahmoud Abdel Hameed; Zuckerbraun, Simon

doi:10.1080/07391102.1991.10507861

Cited by 4 publications

(3 citation statements)

References 18 publications

(20 reference statements)

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“…9-Acridinamine (the name generally used for the compound), one of the simplest representatives of the family of nitrogen organic bases, is a molecule interesting from the cognitive point of view owing to its relatively simple constitution and interesting physicochemical features, which are reflected, among other things, in its ability to interact with biomolecules. , For these reasons, 9-acridinamine has often been used as a model compound in studying the general properties of chemical entities. − Its biological relevance is exhibited by its mutagenic activity, − as well as its ability to interact with DNA ,− and other biologically important molecules. ,− Of some interest is the photodynamic activity of the compound. − 9-Acridinamine is also a convenient fluorescent probe for investigating pH and various physical features of biological systems. − …”

Section: Introductionmentioning

confidence: 99%

“…1,2 For these reasons, 9-acridinamine has often been used as a model compound in studying the general properties of chemical entities. [3][4][5][6] Its biological relevance is exhibited by its mutagenic activity, [7][8][9][10][11][12][13] as well as its ability to interact with DNA 11,[14][15][16][17][18][19] and other biologically important molecules. 15,[20][21][22][23] Of some interest is the photodynamic activity of the compound.…”

Section: Introductionmentioning

confidence: 99%

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Hartree−Fock and Density Functional Methods and IR and NMR Spectroscopies in the Examination of Tautomerism and Features of Neutral 9-Acridinamine in Gaseous and Condensed Media

et al. 1997

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Two tautomeric molecules, 9-acridinamine (9-AA) and 9(10H)-acridinimine (9-AI), were examined at the ab initio Hartree−Fock (HF) and density functional (DFT) levels of theory with the 6-31G** basis sets. Solvent (hexane, CH3CN, H2O) effects were included in ab initio HF optimizations through the self-consistent reaction field (SCRF) technique. Subsequent Hessian calculations followed by the normal-mode analyses revealed all harmonic frequencies to be positive, thus confirming the validity of the geometry optimizations. The energies of the molecules at stationary points corresponding to ab initio HF geometries were supplemented with the second-order Møller−Plesset (MP2) electron correlation correction. Standard routines utilizing relationships of statistical thermodynamics enabled determination of enthalpies of formation (supplemented further with corrections arising from isogyric, hydrogenation, and isodesmic processes) and entropies (heat capacities) at selected temperatures, as well as constants revealing equilibrium between two tautomeric forms. Other physicochemical characteristics, such as bond orders, dipole moments, and energies of the lowest unoccupied (LUMO) and highest occupied (HOMO) molecular orbitals were also obtained from theoretical calculations. Thermochemical data indicate that 9-AA and 9-AI should coexist at ambient temperature. This is also confirmed by a comparison of experimental IR and Raman spectra with harmonic frequencies derived theoretically. 1H and 13C chemical shifts obtained at the GIAO level of theory correlate only qualitatively with relevant experimental NMR data and do not exclude the existence of tautomeric phenomena. The distributions of atomic partial charges and electrostatic potential around the molecules differ noticeably, which implies that 9-AA and 9-AI may behave differently with respect to biomolecules.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Hartree−Fock and Density Functional Methods and IR and NMR Spectroscopies in the Examination of Tautomerism and Features of Neutral 9-Acridinamine in Gaseous and Condensed Media

et al. 1997

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“…[13][14][15] The most spectacular property, however, is undoubtedly the anticancer activity of 9-AA derivatives, 16 -18 which is probably related to the intercalating ability of 9-AA itself. [19][20][21][22][23][24][25] Because the biological features of a compound are strongly connected to its structural characteristics, its propensity to exist in several tautomeric forms may account for the presence or lack of biological activity. It has been shown, for instance, that nitracrine ͑a 9-AA derivative͒ exhibiting anticancer activity 26 crystallizes in its imino form, 27,28 whereas its 2-nitro isomer, lacking antitumor properties, exists, in the solid phase, as a planar amino tautomer.…”

Section: Introductionmentioning

confidence: 99%

Is 9-acridinamine anion a dispersion-bound anion?

Skurski

Rak

Simons

2001

The Journal of Chemical Physics

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The possibility of electron binding to 9-acridinamine ͑9-AA͒ was studied at the second order Møller-Plesset perturbation theory level with the aug-cc-pVDZ basis set augmented with a diffuse 6s6p4d set that has proven appropriate in earlier studies of weakly bound anions. It was found that both the amino and imino tautomers of 9-AA bind an excess electron to form stable anions. The vertical electron attachment energies corresponding to the amino and imino form were calculated to be 20 and 41 cm Ϫ1 , respectively. It was found that while the imino 9-AA tautomer forms a typical dipole-bound anion, the electron binding energy for the amino tautomer calculated at the electrostatic Koopmans' theorem level appears to be cancelled when the correlation correction to the dipole moment of the neutral is taken into account at the MP2 level. Therefore, the stability of the latter anion may be caused only by additional electron correlation effects, which are dominated by dispersion interactions. For this reason, we suggest that this anion may be termed a dispersion-bound anion.

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Extensions to the theory of intercalation

Schellman

Reese

1998

Biopolymers

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Though the nearest neighbor exclusion model provides a good semiquantitative description of intercalation isotherms, it ignores the electrostatic interaction between cationic intercalators and DNA and underestimates binding in the neighborhood of θ = 0.5 intercalators per base pair. In order to improve the analysis and interpretation of intercalative binding curves, we (1) propose and develop a model that permits restricted but partial occupation of nearest neighbor sites, (2) discuss the advantages of using experimental variables for analysis rather than derived variables like θ/L for Scatchard plots, and (3) combine the lattice statistics of intercalation with the electrostatic free energy of intercalation as calculated by C. Bustamante and D. Stigter [(1984) Biopolymers, Vol. 23, pp. 629–645] to generate an isotherm that contains both effects. The analysis of data via the latter theory provides a description of the intercalation not only as a function of ligand concentration but also as a function of ionic strength and θ. The quantitative accuracy of the electrostatic theory can be checked by the standard ln K1 vs ln C plots. [M. T. Record, T. M. Lohman, and P. de Haseth (1976) Journal of Molecular Biology, Vol. 107, pp. 145–158], but appropriate data do not appear to be available at the present time. © 1996 John Wiley & Sons, Inc.

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Polyelectrolyte Effects on 9-Aminoacridine-DNA Binding

Cited by 4 publications

References 18 publications

Hartree−Fock and Density Functional Methods and IR and NMR Spectroscopies in the Examination of Tautomerism and Features of Neutral 9-Acridinamine in Gaseous and Condensed Media

Hartree−Fock and Density Functional Methods and IR and NMR Spectroscopies in the Examination of Tautomerism and Features of Neutral 9-Acridinamine in Gaseous and Condensed Media

Is 9-acridinamine anion a dispersion-bound anion?

Extensions to the theory of intercalation

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