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NAJAJREH, Yousef, Jana KAŠPÁRKOVÁ, María Victoria MARINI PALOMEQUE, Dan GIBSON a Viktor BRABEC. Structural characterization and DNA interactions of new cytotoxic transplatin analogues containing one planar and one nonplanar heterocyclic amine ligand. Online. Journal of Biological Inorganic Chemistry. Germany: Springer Berlin / Heidelberg, 2005, roč. 10, č. 7, s. 722-731. ISSN 0949-8257. [citováno 2024-04-24]

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TY  - JOUR
ID  - 837298
AU  - Najajreh, Yousef - Kašpárková, Jana - Marini Palomeque, María Victoria - Gibson, Dan - Brabec, Viktor
PY  - 2005
TI  - Structural characterization and DNA interactions of new cytotoxic transplatin analogues containing one planar and one nonplanar heterocyclic amine ligand.
JF  - Journal of Biological Inorganic Chemistry
VL  - 10
IS  - 7
SP  - 722-731
EP  - 722-731
PB  - Springer Berlin / Heidelberg
SN  - 09498257
KW  - Platinum
KW  - DNA
KW  - Cross-links
KW  - Cytotoxicity
KW  - X-ray crystallography
N2  - trans-Diaminedicholoroplatinum(II) complexes with one planar and one non-planar heterocyclic amine ligand were designed as new potential antitumor drugs. The X-ray crystallographic structures of trans-[PtCl2(4-picoline)(piperidine)] and trans-[PtCl2(4-picoline)(piperazine)]-HCl revealed that the piperidine and piperazine ligands bind to the platinum through the equatorial position and that the ligands adopt the chair conformation. The nonplatinated amine of the piperazine can form hydrogen bonds with atoms that are approximately 7.5 angstrom away from the Pt binding site. DNA is considered a major pharmacological target of platinum compounds. Hence, to expand the database correlating structural features of platinum compounds and DNA distortions induced by these compounds, which may facilitate identification of more effective anticancer platinum drugs, we describe the DNA binding mode in a cell-free medium of trans-[PtCl2(4-picoline)(piperidine)] and trans-[PtCl2(4-picoline)(piperazine)]-HCl. Interestingly, the overall impact of the replacement of the second ammine group in transplatin by the heterocyclic ligands appears to change the character of the global conformational changes induced in DNA towards that induced by cisplatin. The clinical ineffectiveness of the parent transplatin has been proposed to be also associated with its reduced capability to form bifunctional adducts in double-helical DNA. The results of the present work support the view that replacement of both ammine groups of transplatin by heterocyclic ligands enhances cytotoxicity probably due to the marked enhancement of the stability of intrastrand cross-links in double-helical DNA.
ER  -

Základní údaje
Originální název	Structural characterization and DNA interactions of new cytotoxic transplatin analogues containing one planar and one nonplanar heterocyclic amine ligand.
Název česky	Strukturni charakterizace a interakce s DNA novych cytotoxickych transplatinovych analogu
Autoři	NAJAJREH, Yousef (275 Palestina), Jana KAŠPÁRKOVÁ (203 Česká republika), María Victoria MARINI PALOMEQUE (858 Uruguay), Dan GIBSON (376 Izrael) a Viktor BRABEC (203 Česká republika, garant)
Vydání	Journal of Biological Inorganic Chemistry, Germany, Springer Berlin / Heidelberg, 2005, 0949-8257.

Další údaje
Originální jazyk	angličtina
Typ výsledku	Článek v odborném periodiku
Obor	10610 Biophysics
Stát vydavatele	Německo
Utajení	není předmětem státního či obchodního tajemství
Impakt faktor	Impact factor: 3.224
Kód RIV	RIV/00216224:14310/05:00035838
Organizační jednotka	Přírodovědecká fakulta
UT WoS	000233238600002
Klíčová slova česky	Platina; DNA; retezcove mustky; cytotoxicita; rentgenová krystalografie
Klíčová slova anglicky	Platinum ; DNA ; Cross-links ; Cytotoxicity ; X-ray crystallography
Štítky	Cross-links, cytotoxicity, DNA, platinum, X-ray crystallography
Příznaky	Mezinárodní význam, Recenzováno
Změnil	Změnila: Mgr. María Victoria Marini Palomeque, Ph.D., učo 22912. Změněno: 25. 6. 2009 12:38.

Anotace
trans-Diaminedicholoroplatinum(II) complexes with one planar and one non-planar heterocyclic amine ligand were designed as new potential antitumor drugs. The X-ray crystallographic structures of trans-[PtCl2(4-picoline)(piperidine)] and trans-[PtCl2(4-picoline)(piperazine)]-HCl revealed that the piperidine and piperazine ligands bind to the platinum through the equatorial position and that the ligands adopt the chair conformation. The nonplatinated amine of the piperazine can form hydrogen bonds with atoms that are approximately 7.5 angstrom away from the Pt binding site. DNA is considered a major pharmacological target of platinum compounds. Hence, to expand the database correlating structural features of platinum compounds and DNA distortions induced by these compounds, which may facilitate identification of more effective anticancer platinum drugs, we describe the DNA binding mode in a cell-free medium of trans-[PtCl2(4-picoline)(piperidine)] and trans-[PtCl2(4-picoline)(piperazine)]-HCl. Interestingly, the overall impact of the replacement of the second ammine group in transplatin by the heterocyclic ligands appears to change the character of the global conformational changes induced in DNA towards that induced by cisplatin. The clinical ineffectiveness of the parent transplatin has been proposed to be also associated with its reduced capability to form bifunctional adducts in double-helical DNA. The results of the present work support the view that replacement of both ammine groups of transplatin by heterocyclic ligands enhances cytotoxicity probably due to the marked enhancement of the stability of intrastrand cross-links in double-helical DNA.

Anotace

trans-Diaminedicholoroplatinum(II) complexes with one planar and one non-planar heterocyclic amine ligand were designed as new potential antitumor drugs. The X-ray crystallographic structures of trans-[PtCl2(4-picoline)(piperidine)] and trans-[PtCl2(4-picoline)(piperazine)]-HCl revealed that the piperidine and piperazine ligands bind to the platinum through the equatorial position and that the ligands adopt the chair conformation. The nonplatinated amine of the piperazine can form hydrogen bonds with atoms that are approximately 7.5 angstrom away from the Pt binding site. DNA is considered a major pharmacological target of platinum compounds. Hence, to expand the database correlating structural features of platinum compounds and DNA distortions induced by these compounds, which may facilitate identification of more effective anticancer platinum drugs, we describe the DNA binding mode in a cell-free medium of trans-[PtCl2(4-picoline)(piperidine)] and trans-[PtCl2(4-picoline)(piperazine)]-HCl. Interestingly, the overall impact of the replacement of the second ammine group in transplatin by the heterocyclic ligands appears to change the character of the global conformational changes induced in DNA towards that induced by cisplatin. The clinical ineffectiveness of the parent transplatin has been proposed to be also associated with its reduced capability to form bifunctional adducts in double-helical DNA. The results of the present work support the view that replacement of both ammine groups of transplatin by heterocyclic ligands enhances cytotoxicity probably due to the marked enhancement of the stability of intrastrand cross-links in double-helical DNA.

Anotace česky
trans-Diaminedicholoroplatinum(II) komplexy s jedním planárním a jedním neplanarním heterocyklickým aminovým lingandem byli navrženy jako nové potenciální protinadorové léky.