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Synthesis, Crystal Structure and DNA Binding Studies of Bis(piperidinium)bis-(N,N,N',N'-tetramethylethylenediammonium) Decavanadate(V) Tetrahydrate

Jiang M., Li Y. -T., Wu Z. -Y., Yan C. -W.

Polish Journal of Chemistry

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2009

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Vol. 83, nr 11

1849-1858

EN

A new decavanadate compound consisting of one decavanadate polyanion [V10O28]6–, two protonated piperidinium cations [C5H12N]+, two doubly protonated N,N,N',N'- tetramethylethylenediammonium cat ions [C6N2H18]2+ and four lattice water molecules, namely, [(C5H12N)2][(C6N2H18)2][V10O28]×4H2O, has been synthesized and characterized by spectroscopic (IR, UV-vis and ESR) studies and single-crystal X-ray diffraction. It crystallizes in the monoclinic system, space group P21/n and Z = 2, with a = 11.1267(18) capital A, ring, b = 16.854(3) capital A, ring, c = 12.973(2) capital A, ring and beta = 95.426(2)°. The cat ions, an ions and lattice water molecules are assembled by hydrogen bonds, forming a three-dimensional supramolecular architecture. The DNA-binding property of the compound was preliminarily investigated by using fluorescence spectrum, and the results indicating that the interaction mode between the compound and herring sperm DNA (HS-DNA) might be groove binding with the quenching constant of 1.20×104. To the best of our knowledge, this is the first report about the DNA-binding study of decavanadate compounds.

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Interactions of the Oxidation Products of Papaverine with Guanine Quadruplexes

Mądry L., Gałęzowska E., Głuszyńska A., Hermann T., Zabel M., Juskowiak B.

Polish Journal of Chemistry

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2006

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Vol. 80, nr 6

921-929

EN

The interactions of G-quadruplex DNA with two oxidation products of papaverine, 6a,12a-diazadibenzo-[a,g]fluorenylium derivative (1) and 2,3,9,10-tetramethoxy-12- oxo-12H-indolo[2,1-a]isoquinolinium cation (2) were investigated. Effect of the organic modifier (EtOH) and NaCl on the spectral properties and aggregation of free ligands and on the DNA-binding affinity were assessed. Ligand 1 exhibited tendency for aggregation and showed higher binding selectivity for G-quadruplex DNA over double-stranded DNA. Both ligands were capable of interacting with DNA according to three binding modes: (i) electrostatic interactions, (ii) classical intercalation to dsDNA, and (iii) the specific binding to quadruplex DNA. The cytotoxic activity of ligand 2 was generally higher than that for ligand 1, approaching a micromolar concentration level that may suggest its telomerase inhibition activity.

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Spectral Properties and DNA-binding Study of 6a, 12a-Diazadibenzo-[a,g]fluorenylium Derivative

Juskowiak B., Gałęzowska E., Kościelna H., Hermann T., Piotrowska K.

Polish Journal of Chemistry

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2005

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Vol. 79 / nr 5

831-844

EN

The DNA binding affinity and anion effect on the aggregation of a G-quadruplex selective ligand, 6a,12a-diazadibenzo-[a,g]fluorenylium derivative, were studied by UV-Vis absorption, molecular modeling and fluorescence spectroscopy. The anion character and its concentration influenced the spectral properties of ligand aggregates. Observed spectral peculiarities were discussed in terms of the formation of H- and J-type aggregates. The DNA binding mode and affinity of the ligand depended on the salt concentration; preferential binding to G-quadruplexDNAwas clearly seen at higher salt concentration.

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Rational Design, synthesis and Biological Evaluation of 3H-Naphtho[1,2,3-de]quinoline-2,7-diones: a New Class of Potential Antitumor Agents

Antonini L., Polucci P., Magnano A., Sparapani S., Martelli S.

Polish Journal of Chemistry

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2004

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Vol. 78 / nr 8

1019-1025

EN

A series of novel potential DNA-binding antitumor agents, 6-[(_-aminoalkyl)amino]- 3H-naphtho[1,2,3-de]quinoline-2,7-diones 3a-j, has been prepared by nucleophilic substitution of commercially available 6-bromo-4-methyl-1-phenyl-3Hnaphtho[ 1,2,3-de]quinoline-2,7-dione with the suitable 1-[_-(alkylamino)alkyl]amine. In vitro cytotoxic potencies of these derivatives toward six tumor cell lines, including human colon adenocarcinoma (HT29) and human ovarian carcinoma (A2780 sensitive, A2780cisR cisplatin-resistant, CH1, CH1cisR cisplatin-resistant, and SKOV-3), are described and compared to that of reference drugs. The 6-[3-(diethylamino)propyl]- 3H-naphtho[1,2,3-de]quinoline-2,7-diones (3e), which possesses good cytotoxicity and low or none cross resistance with Cs on resistant cell lines, can be regarded as a new lead in the development of intercalating anticancer derivatives.