Abstract
The alkylhydroxybenzene (AHB) autoregulatory factors d 1 (fd 1) of microorganisms have been found to directly interact with highly polymeric DNA. This circumstance results in changes, related to alterations in the topology of this macromolecule, in DNA physicochemical properties. The physicochemical properties of DNA in the presence of chemical analogues of microbial AHBs (methylresorcinol; hexylresorcinol; and 2-(4-hydroxyphenyl)ethane-1-ol, also known as tyrosol) were investigated using adsorption spectrophotometry, fluorometry, heat denaturation, viscosimetry, and electrophoresis in agarose gel. A number of concordant effects pointing to DNA-AHB interactions were revealed that manifest themselves in the hypochromic properties of the resulting complexes, an increase in their melting temperature and viscosity, a decrease in their electrophoretic mobility, and a change in the fluorescent properties of AHBs upon complexation with DNA. Such alterations were particularly significant in the presence of hexylresorcinol, which possessed the maximum alkyl radical length among the fd 1 analogues tested. Using atomic force microscopy, we visualized the micellelike DNA structures forming in the presence of AHBs. The results obtained provided the basis for developing a hypothetical model of the interaction between the biopolymer macromolecule and low-molecular-weight AHBs that takes into account the differences in the hydrophobicity of individual AHB homologues functioning as ligands. In terms of our model, we discuss AHB involvement in the stabilization of DNA and alteration of its topology, i.e., in the process related to intragenomic rearrangements, which account for the intrapopulational variability of bacteria, including dissociation processes.
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REFERENCES
Osipov, G.A., El'-Registan, G.I., Svetlichnyi, V.A., Kozlova, A.N., Duda, V.I., Kaprel'yants, A.S., and Pomazanov, V.V., On the Chemical Nature of the d1 Autoregulatory Factor of Pseudomonas carboxydoflava, Mikrobiologiya, 1985, vol. 54, no.2, pp. 186–190.
Batrakov, S.G., El'-Registan, G.I., Pridachina, N.N., Nenashev, V.A., Kozlova, A.N., Gryaznova, M.N., and Zolotareva, I.N., Tyrosol Is the d1 Autoregulatory Factor of the yeast Saccharomyces cerevisiae, Mikrobiologiya, 1993, vol. 62, no.4, pp. 633–638.
Kaprel'yants, A.S., El'-Registan, G.I., Suleimenov, M.K., Sorokina, A.D., Deborin, G.A., Stoyanovich, F.M., Lille, Yu.E., and Ostrovskii, D.N., Structural and Functional Changes in Bacterial and Model Membranes under the Action of Phenolic Lipids, Biol. Membr., 1987, vol. 4, pp. 373–379.
Bespalov, M.M., Kolpakov, A.I., Loiko, N.G., Doroshenko, E.V., Mulyukin, A.L., Kozlova, A.N., Varlamova, E.A., Kurganov, B.I., and El'-Registan, G.I., The Role of Microbial Dormancy Autoinducers in Metabolism Blockade, Mikrobiologiya, 2000, vol. 69, no.2, pp. 217–223.
Martirosova, E.I., Karpekina, T.A., and El'-Registan, G.I., Enzyme Modification by Natural Chemical Chaperons of Microorganisms, Mikrobiologiya, 2004, vol. 73, no.5, pp. 708–715.
Mulyukin, A.L., Lusta, K.A., Gryaznova, M.N., Kozlova, A.N., Duzha, M.V., Duda, V.I., and El'-Registan, G.I., Formation of Resting Cells by Bacillus cereus and Micrococcus luteus, Mikrobiologiya, 1996, vol. 65, no.6, pp. 782–789.
Stepanenko, I.Yu., Strakhovskaya, M.G., Belenikina, N.S., Nikolaev, Yu.A., Mulyukin, A.L., Revina, A.A., and El'-Registan, G.I., Protection of Saccharomyces cerevisiae against Oxidative and Radiation-Caused Damage by Alkylhydroxybenzenes, Mikrobiologiya, 2004, vol. 73, no.2, pp. 204–210.
Margulis, A.B., Il'inskaya, O.B., Kolpakov, A.I., and El'-Registan, G.I., Induction of SOS Response of the Cell under the Effect of Microbial Autoregulatory Factors, Genetika, 2003, vol. 39, no.9, pp. 1180–1184.
Gasiorowski, K., Szyba, K., Brokos, B., and Kozubek, A., Antimutagenic Activity of Alkylresorcinols from Cereal Grains, Cancer Lett., 1996, vol. 106, pp. 109–115.
Il'inskaya, O.N., Kolpakov, A.I., Zelenikhin, P.V., Kruglova, Z.F., Choidash, B., Doroshenko, E.V., Mulyukin, A.L., and El'-Registan, G.I., The Effect of Anabiosis Autoinducers on the Bacterial Genome, Mikrobiologiya, 2002, vol. 71, no.2, pp. 194–199.
Singh, U.S., Scannell, R.T., An, H., Carter, B.J., and Hecht, S.M., DNA Cleavage by Di-and Trihydroxyalkylbenzenes: Characterization of Products and Roles of O2, Cu(II), and Alkali, J. Am. Chem. Soc., 1995, vol. 117, no.51, pp. 12691–12699.
Mulyukin, A.L., Vakhrushev, M.A., Strazhevskaya, N.B., Shmyrina, A.S., Kozlova, A.N., Zhdanov, R.I., Suzina, N.E., Duda, V.I., and El'-Registan, G.I., Effect of Alkylhydroxybenzenes, Microbial Anabiosis Inducers, on the Structural Organization of Pseudomonas aurantiaca DNA and on the Induction of Phenotypic Dissociation, Mikrobiologiya, 2005, vol. 74, no.2, pp. 157–165.
Saenger, W., Principles of Nucleic Acid Structure, Cantor, C.R., Ed., New York: Springer, 1984.
Hladyszowski, J., Zubik, L., and Kozubek, A., Quantum Mechanical and Experimental Oxidation Studies of Pentadecylresorcinol, Olivetol, Orcinol and Resorcinol, Free Rad. Res., 1998, vol. 28, pp. 359–368.
Lakovich, Dzh., Osnovy fluorestsentnoi mikroskopii (Fundamentals of Fluorescent Microscopy), Moscow: Mir, 1986.
Kozubek, A. and Tyman, J.H.P., Resorcinolic Lipids, the Natural Non-Isoprenoid Phenolic Amphiphiles and Their Biological Activity, Chem. Rev., 1999, vol. 99, no.1, pp. 1–31.
Revina, A.A., Larionov, O.G., Kochetova, M.V., Lutsik, T.K., and El'-Registan, G.I., Spectrophotometric and Chromatographic Studies of the Products of Radiolysis of Aerated Aqueous Solutions of Alkylresorcinols, Izv. Ross. Akad. Nauk, Ser. Khim., 2003, no. 11, pp. 2257–2263.
Davydova, O.V. and Kargov, S.I., The Effect of Dielectric Permeability of the Solvent and DNA concentration on the Process of Its Thermal Denaturation in Water-Organic Solutions, Vestn. Mosk. Univ., Ser. 2: Khim., 1999, vol. 40, no.3, pp. 152–154.
Sukhorukov, B.I., Petrov, A.I., Kazaryan, R.L., and Kuvichkin, V.V., The Effect of the Hydrocarbon Chain and the Structure of the Ionic Fragment of the Cationic Amphiphile on Its Complexation with DNA, Tez. II S"ezda biofizikov Rossii. Razdel 2: Struktura i dinamika nukleinovykh kislot i ih kompleksov (Abstr. 2nd Meeting of Russian Biophysicists. Section 2: Structure and Dynamics of Nucleic Acids and Their Complexes), Moscow, 1999.
Petrov, A.I., Kazaryan, R.L., and Sukhorukov, B.I., The Effect of Cationic Amphiphiles of the N-Trimethylalkyl Series on the Parameters of DNA Melting Curves, Tez. VII S"ezda biofizikov Rossii. Razdel 2: Struktura i dinamika nukleinovykh kislot i ih kompleksov (Abstr. 7th Meeting of Russian Biophysicists. Section 2: Structure and Dynamics of Nucleic Acids and Their Complexes), Moscow, 2004.
Il'inskaya, O.N., Kolpakov, A.I., Mulyukin, A.L., Dreier, F., and El'-Registan, G.I., The Effect of Membrane-Active Microbial Autoregulators on the Growth of the Growth of a Culture of ras-Transformed Mouse Fibroblasts, Prikl. Biokhim. Mikrobiol., 2000, vol. 62, no.5, pp. 475–480.
Zhdanov, K.I., D'yachkov, E.P., Struchkov, V.A., Strazhevskaya, N.B., and D'yachkov, P.N., DNA-Binding Lipids: Modeling of the Interaction of DNA with Stearic and Unsaturated Fatty Acids, Izv. Ross. Akad. Nauk, Ser. Khim., 2003, no. 9, pp. 1794–1800.
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Translated from Mikrobiologiya, Vol. 74, No. 5, 2005, pp. 616–625.
Original Russian Text Copyright © 2005 by Davydova, Deryabin, Nikiyan, El'-Registan.
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Davydova, O.K., Deryabin, D.G., Nikiyan, A.N. et al. Mechanisms of Interaction between DNA and Chemical Analogues of Microbial Anabiosis Autoinducers. Microbiology 74, 533–541 (2005). https://doi.org/10.1007/s11021-005-0100-1
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DOI: https://doi.org/10.1007/s11021-005-0100-1