Structural Characterization, DNA Interactions, and Cytotoxicity
of New Transplatin Analogues Containing One Aliphatic and One
Planar Heterocyclic Amine Ligand

J 2006

Structural Characterization, DNA Interactions, and Cytotoxicity of New Transplatin Analogues Containing One Aliphatic and One Planar Heterocyclic Amine Ligand

RAMOS-LIMA, Francisco J., Oldřich VRÁNA, Adoración G. QUIROGA, Carmen NAVARRO-RANNINGER, Anna HALÁMIKOVÁ et. al.

Basic information

Original name

Structural Characterization, DNA Interactions, and Cytotoxicity of New Transplatin Analogues Containing One Aliphatic and One Planar Heterocyclic Amine Ligand

Name in Czech

Strukturní charakterizace, interakce s DNA, a cytotoxicita nových transplatinových analogů obsahujících jeden alifatický a jeden heterocyklický amino ligand

Authors

RAMOS-LIMA, Francisco J. (724 Spain), Oldřich VRÁNA (203 Czech Republic), Adoración G. QUIROGA (724 Spain), Carmen NAVARRO-RANNINGER (724 Spain), Anna HALÁMIKOVÁ (703 Slovakia), Hana RYBNÍČKOVÁ (203 Czech Republic), Lenka HEJMALOVÁ (203 Czech Republic) and Viktor BRABEC (203 Czech Republic, guarantor)

Edition

Journal of Medicinal Chemistry, USA, American Chemical Society, 2006, 0022-2623

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10610 Biophysics

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

Impact factor

Impact factor: 5.115

Organization unit

Faculty of Science

UT WoS

000236979100029

Keywords (in Czech)

transplatina; protinádorový; DNA

Keywords in English

transplatin; antitumor; DNA

Abstract

ORIG CZ

V originále

We report in the present work new analogues of clinically ineffective transplatin in which one ammine group was replaced by aliphatic and the other by a planar heterocyclic ligand, namely trans-[PtCl(2)(isopropylamine)(3-(hydroxymethyl)-pyridine)], 1, and trans-[PtCl(2)(isopropylamine)(4-(hydroxymethyl)-pyridine)], 2. The new compounds, in comparison with parent transplatin, exhibit radically enhanced activity in tumor cell lines both sensitive and in particular resistant to cisplatin. Concomitantly, the DNA binding mode of 1 and 2 compared to parent transplatin and other antitumor analogues of transplatin in which only one ammine group was replaced is also different. The results also suggest that the reactions of glutathione and metallothionein-2 with compounds 1 and 2 do not play a crucial role in their overall biological effects. In addition, the monofunctional adducts of 1 and 2 are quenched by glutathione considerably less than the adducts of transplatin, which may potentiate cytotoxic effects of these new platinum complexes.

In Czech

Tato práce popisuje nové analogy klinicky neúčinné tranplatiny, kde je nahrazena jedna aminoskupina alifatickým řetězcem a druhá aminoskupina je nahrazena planárním heterocyklickým ligantem,a to trans-[PtCl(2)(isopropylamine)(3-(hydroxymethyl)-pyridine)], 1, and trans-[PtCl(2)(isopropylamine)(4-(hydroxymethyl)-pyridine)], 2.

Citovat

RAMOS-LIMA, Francisco J., Oldřich VRÁNA, Adoración G. QUIROGA, Carmen NAVARRO-RANNINGER, Anna HALÁMIKOVÁ, Hana RYBNÍČKOVÁ, Lenka HEJMALOVÁ and Viktor BRABEC. Structural Characterization, DNA Interactions, and Cytotoxicity of New Transplatin Analogues Containing One Aliphatic and One Planar Heterocyclic Amine Ligand. Journal of Medicinal Chemistry. USA: American Chemical Society, 2006, vol. 49, No 8, p. 2640-2651. ISSN 0022-2623.

@article{837777,
   author = {RamosandLima, Francisco J. and Vrána, Oldřich and Quiroga, Adoración G. and NavarroandRanninger, Carmen and Halámiková, Anna and Rybníčková, Hana and Hejmalová, Lenka and Brabec, Viktor},
   article_location = {USA},
   article_number = {8},
   keywords = {transplatin; antitumor; DNA},
   language = {eng},
   issn = {0022-2623},
   journal = {Journal of Medicinal Chemistry},
   title = {Structural Characterization, DNA Interactions, and Cytotoxicity of New Transplatin Analogues Containing One Aliphatic and One Planar Heterocyclic Amine Ligand},
   volume = {49},
   year = {2006}
}

TY  - JOUR
ID  - 837777
AU  - Ramos-Lima, Francisco J. - Vrána, Oldřich - Quiroga, Adoración G. - Navarro-Ranninger, Carmen - Halámiková, Anna - Rybníčková, Hana - Hejmalová, Lenka - Brabec, Viktor
PY  - 2006
TI  - Structural Characterization, DNA Interactions, and Cytotoxicity of New Transplatin Analogues Containing One Aliphatic and One Planar Heterocyclic Amine Ligand
JF  - Journal of Medicinal Chemistry
VL  - 49
IS  - 8
SP  - 2640-2651
EP  - 2640-2651
PB  - American Chemical Society
SN  - 00222623
KW  - transplatin
KW  - antitumor
KW  - DNA
N2  - We report in the present work new analogues of clinically ineffective transplatin in which one ammine group was replaced by aliphatic and the other by a planar heterocyclic ligand, namely trans-[PtCl(2)(isopropylamine)(3-(hydroxymethyl)-pyridine)], 1, and trans-[PtCl(2)(isopropylamine)(4-(hydroxymethyl)-pyridine)], 2. The new compounds, in comparison with parent transplatin, exhibit radically enhanced activity in tumor cell lines both sensitive and in particular resistant to cisplatin. Concomitantly, the DNA binding mode of 1 and 2 compared to parent transplatin and other antitumor analogues of transplatin in which only one ammine group was replaced is also different. The results also suggest that the reactions of glutathione and metallothionein-2 with compounds 1 and 2 do not play a crucial role in their overall biological effects. In addition, the monofunctional adducts of 1 and 2 are quenched by glutathione considerably less than the adducts of transplatin, which may potentiate cytotoxic effects of these new platinum complexes.
ER  -

RAMOS-LIMA, Francisco J., Oldřich VRÁNA, Adoración G. QUIROGA, Carmen NAVARRO-RANNINGER, Anna HALÁMIKOVÁ, Hana RYBNÍČKOVÁ, Lenka HEJMALOVÁ and Viktor BRABEC. Structural Characterization, DNA Interactions, and Cytotoxicity of New Transplatin Analogues Containing One Aliphatic and One Planar Heterocyclic Amine Ligand. \textit{Journal of Medicinal Chemistry}. USA: American Chemical Society, 2006, vol.~49, No~8, p.~2640-2651. ISSN~0022-2623.

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