International Journal of Biological Macromolecules, volume 41, issue 4, pages 415-422

DNA binding properties and evaluation of cytotoxic activity of 9,10-bis-N-substituted (aminomethyl)anthracenes

Kozurkova Maria ¹

Sabolová Danica ¹

Paulíková H ²

Janovec L ³

Kristian P. ³

Bajdichová M. ²

Buša Ján ⁴

Podhradský D ¹

Imrich Ján ³

Hide authors affiliations Show authors affiliations: 4 affiliations

Department of Biochemistry, Institute of Chemistry, Faculty of Science, P.J. Šafárik University, Moyzesova 11, 04167 Košice, Slovak Republic |

Department of Biochemistry and Microbiology, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, 81237 Bratislava, Slovak Republic |

Department of Organic Chemistry, Institute of Chemistry, Faculty of Science, P.J. Šafárik University, Moyzesova 11, 04167 Košice, Slovak Republic |

⁴

Department of Mathematics, Faculty of Electrical Engineering and Informatics, Technical University of Košice, B. Němcovej 32, 04200 Košice, Slovak Republic |

Publication type: Journal Article

Publication date: 2007-10-01

Elsevier

Journal: International Journal of Biological Macromolecules

Quartile SCImago

Quartile WOS

Impact factor: 8.2

ISSN: 01418130, 18790003

DOI: 10.1016/j.ijbiomac.2007.05.013

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Biochemistry

Molecular Biology

General Medicine

Structural Biology

Abstract

The results of DNA binding properties for four selected N-substituted 9,10-bis(aminomethyl)anthracenes are presented. DNA binding affinities were studied using UV-vis and fluorescence spectrophotometric titrations, CD spectroscopy, denaturation transition temperature (Tm) measurements and AM1 quantum chemical calculations. The results obtained indicate that the anthracene products intercalate into the stacked base pairs of DNA with binding constants, K, in the range 1.3-10.9 x 10(5)M(-1) and the binding site size in DNA-base pairs, n, extending over the range 2.4-4.6. Tm values increased in the presence of the anthryl probes, thereby reflecting an increased stability of the calf-thymus (CT) DNA double helix and rendering agreement with the spectrometric titration results. The synthesized compounds were tested against L1210 and HeLa tumor cell lines wherein the HeLa cells appeared to be more sensitive than the L1210 cells. 9,10-Bis{[2-(piperazin-1-yl)ethyl]aminomethyl}anthracene exhibited the highest activity of the tested compounds. Our findings were compared with those of a control drug bisantrene.

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Citations by journals

	1 2 3 4 5
Bioorganic and Medicinal Chemistry Letters	Bioorganic and Medicinal Chemistry Letters, 5, 12.5% Bioorganic and Medicinal Chemistry Letters 5 publications, 12.5%
Heterocycles	Heterocycles, 3, 7.5% Heterocycles 3 publications, 7.5%
International Journal of Biological Macromolecules	International Journal of Biological Macromolecules, 3, 7.5% International Journal of Biological Macromolecules 3 publications, 7.5%
Medicinal Chemistry Research	Medicinal Chemistry Research, 2, 5% Medicinal Chemistry Research 2 publications, 5%
Tetrahedron Letters	Tetrahedron Letters, 1, 2.5% Tetrahedron Letters 1 publication, 2.5%
Ionics	Ionics, 1, 2.5% Ionics 1 publication, 2.5%
Catalysis Letters	Catalysis Letters, 1, 2.5% Catalysis Letters 1 publication, 2.5%
Journal of Chemical Sciences	Journal of Chemical Sciences, 1, 2.5% Journal of Chemical Sciences 1 publication, 2.5%
Molecular Biology Reports	Molecular Biology Reports, 1, 2.5% Molecular Biology Reports 1 publication, 2.5%
Bulletin of the Korean Chemical Society	Bulletin of the Korean Chemical Society, 1, 2.5% Bulletin of the Korean Chemical Society 1 publication, 2.5%
Toxicology in Vitro	Toxicology in Vitro, 1, 2.5% Toxicology in Vitro 1 publication, 2.5%
Bioorganic and Medicinal Chemistry	Bioorganic and Medicinal Chemistry, 1, 2.5% Bioorganic and Medicinal Chemistry 1 publication, 2.5%
European Journal of Medicinal Chemistry	European Journal of Medicinal Chemistry, 1, 2.5% European Journal of Medicinal Chemistry 1 publication, 2.5%
Journal of Molecular Structure THEOCHEM	Journal of Molecular Structure THEOCHEM, 1, 2.5% Journal of Molecular Structure THEOCHEM 1 publication, 2.5%
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 1, 2.5% Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy 1 publication, 2.5%
Chinese Chemical Letters	Chinese Chemical Letters, 1, 2.5% Chinese Chemical Letters 1 publication, 2.5%
Bioorganic Chemistry	Bioorganic Chemistry, 1, 2.5% Bioorganic Chemistry 1 publication, 2.5%
Chemico-Biological Interactions	Chemico-Biological Interactions, 1, 2.5% Chemico-Biological Interactions 1 publication, 2.5%
Journal of Molecular Structure	Journal of Molecular Structure, 1, 2.5% Journal of Molecular Structure 1 publication, 2.5%
Chemical Biology and Drug Design	Chemical Biology and Drug Design, 1, 2.5% Chemical Biology and Drug Design 1 publication, 2.5%
Journal of Physical Chemistry B	Journal of Physical Chemistry B, 1, 2.5% Journal of Physical Chemistry B 1 publication, 2.5%
Inorganic Chemistry	Inorganic Chemistry, 1, 2.5% Inorganic Chemistry 1 publication, 2.5%
Journal of Physical Chemistry C	Journal of Physical Chemistry C, 1, 2.5% Journal of Physical Chemistry C 1 publication, 2.5%
RSC Advances	RSC Advances, 1, 2.5% RSC Advances 1 publication, 2.5%
Chemical Communications	Chemical Communications, 1, 2.5% Chemical Communications 1 publication, 2.5%
MedChemComm	MedChemComm, 1, 2.5% MedChemComm 1 publication, 2.5%
Nucleosides, Nucleotides and Nucleic Acids	Nucleosides, Nucleotides and Nucleic Acids, 1, 2.5% Nucleosides, Nucleotides and Nucleic Acids 1 publication, 2.5%
Journal of Biomolecular Structure and Dynamics	Journal of Biomolecular Structure and Dynamics, 1, 2.5% Journal of Biomolecular Structure and Dynamics 1 publication, 2.5%
Nucleic Acids Research	Nucleic Acids Research, 1, 2.5% Nucleic Acids Research 1 publication, 2.5%
Journal of Pharmacy and Pharmacology	Journal of Pharmacy and Pharmacology, 1, 2.5% Journal of Pharmacy and Pharmacology 1 publication, 2.5%
	1 2 3 4 5

Citations by publishers

	2 4 6 8 10 12 14 16 18
Elsevier	Elsevier, 18, 45% Elsevier 18 publications, 45%
Springer Nature	Springer Nature, 6, 15% Springer Nature 6 publications, 15%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 4, 10% Royal Society of Chemistry (RSC) 4 publications, 10%
The Japan Institute of Heterocyclic Chemistry	The Japan Institute of Heterocyclic Chemistry, 3, 7.5% The Japan Institute of Heterocyclic Chemistry 3 publications, 7.5%
Wiley	Wiley, 3, 7.5% Wiley 3 publications, 7.5%
American Chemical Society (ACS)	American Chemical Society (ACS), 3, 7.5% American Chemical Society (ACS) 3 publications, 7.5%
Taylor & Francis	Taylor & Francis, 2, 5% Taylor & Francis 2 publications, 5%
Oxford University Press	Oxford University Press, 1, 2.5% Oxford University Press 1 publication, 2.5%
	2 4 6 8 10 12 14 16 18

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Kozurkova M. et al. DNA binding properties and evaluation of cytotoxic activity of 9,10-bis-N-substituted (aminomethyl)anthracenes // International Journal of Biological Macromolecules. 2007. Vol. 41. No. 4. pp. 415-422.

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Kozurkova M., Sabolová D., Paulíková H., Janovec L., Kristian P., Bajdichová M., Buša J., Podhradský D., Imrich J. DNA binding properties and evaluation of cytotoxic activity of 9,10-bis-N-substituted (aminomethyl)anthracenes // International Journal of Biological Macromolecules. 2007. Vol. 41. No. 4. pp. 415-422.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.ijbiomac.2007.05.013

UR - https://doi.org/10.1016%2Fj.ijbiomac.2007.05.013

TI - DNA binding properties and evaluation of cytotoxic activity of 9,10-bis-N-substituted (aminomethyl)anthracenes

T2 - International Journal of Biological Macromolecules

AU - Kozurkova, Maria

AU - Sabolová, Danica

AU - Paulíková, H

AU - Janovec, L

AU - Kristian, P.

AU - Bajdichová, M.

AU - Buša, Ján

AU - Podhradský, D

AU - Imrich, Ján

PY - 2007

DA - 2007/10/01 00:00:00

PB - Elsevier

SP - 415-422

IS - 4

VL - 41

SN - 0141-8130

SN - 1879-0003

ER -

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@article{2007_Kozurkova,

author = {Maria Kozurkova and Danica Sabolová and H Paulíková and L Janovec and P. Kristian and M. Bajdichová and Ján Buša and D Podhradský and Ján Imrich},

title = {DNA binding properties and evaluation of cytotoxic activity of 9,10-bis-N-substituted (aminomethyl)anthracenes},

journal = {International Journal of Biological Macromolecules},

year = {2007},

volume = {41},

publisher = {Elsevier},

month = {oct},

url = {https://doi.org/10.1016%2Fj.ijbiomac.2007.05.013},

number = {4},

pages = {415--422},

doi = {10.1016/j.ijbiomac.2007.05.013}

}

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MLA Copy

Kozurkova, Maria, et al. “DNA binding properties and evaluation of cytotoxic activity of 9,10-bis-N-substituted (aminomethyl)anthracenes.” International Journal of Biological Macromolecules, vol. 41, no. 4, Oct. 2007, pp. 415-422. https://doi.org/10.1016%2Fj.ijbiomac.2007.05.013.

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Publisher

Elsevier

Journal

International Journal of Biological Macromolecules

Quartile SCImago

Quartile WOS

Impact factor

8.2

ISSN

01418130 (Print)
18790003 (Electronic)