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Structure and Unique Interactions with DNA of a Cationic Trans-Platinum Complex with the Nonplanar Bicyclic Piperidinopiperidine Ligand^†

Yousef Najajreh Dr.

Department of Medicinal Chemistry and Natural Products, School of Pharmacy, The Hebrew University of Jerusalem, Jerusalem 91120, Israel, Fax: (+972) 2-675-7076

Current address: Department of Medicinal Chemistry and Natural Products, Faculty of Pharmacy/Al-Quds University, Jerusalem, P.O.Box 20002 (Palestine)

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Dmitri Prilutski,

Dmitri Prilutski

Interdepartmental Equipment Unit, The Hebrew University-Hadassah Medical School, Jerusalem 91120, Israel

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Yael Ardeli-Tzaraf,

Yael Ardeli-Tzaraf

Department of Medicinal Chemistry and Natural Products, School of Pharmacy, The Hebrew University of Jerusalem, Jerusalem 91120, Israel, Fax: (+972) 2-675-7076

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Jose Manuel Perez Dr.,

Jose Manuel Perez Dr.

Departamento de Química Inorgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049-Madrid, Spain

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Elena Khazanov,

Elena Khazanov

Laboratory of Membrane and Liposome Research, Department of Biochemistry, The Hebrew University-Hadassah Medical School, Jerusalem 91120, Israel

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Yechezkel Barenholz Prof.,

Yechezkel Barenholz Prof.

Laboratory of Membrane and Liposome Research, Department of Biochemistry, The Hebrew University-Hadassah Medical School, Jerusalem 91120, Israel

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Jana Kasparkova Dr.,

Jana Kasparkova Dr.

Institute of Biophysics, Academy of Sciences of the Czech Republic, 61265 Brno, Czech Republic

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Viktor Brabec Prof.,

Viktor Brabec Prof.

Institute of Biophysics, Academy of Sciences of the Czech Republic, 61265 Brno, Czech Republic

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Dan Gibson Dr.,

Dan Gibson Dr.

[email protected]

Department of Medicinal Chemistry and Natural Products, School of Pharmacy, The Hebrew University of Jerusalem, Jerusalem 91120, Israel, Fax: (+972) 2-675-7076

Affiliated with the David R. Bloom, Center for Pharmacy at The Hebrew University of Jerusalem, Israel.

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Yousef Najajreh Dr.,

Yousef Najajreh Dr.

Department of Medicinal Chemistry and Natural Products, School of Pharmacy, The Hebrew University of Jerusalem, Jerusalem 91120, Israel, Fax: (+972) 2-675-7076

Current address: Department of Medicinal Chemistry and Natural Products, Faculty of Pharmacy/Al-Quds University, Jerusalem, P.O.Box 20002 (Palestine)

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Dmitri Prilutski,

Dmitri Prilutski

Interdepartmental Equipment Unit, The Hebrew University-Hadassah Medical School, Jerusalem 91120, Israel

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Yael Ardeli-Tzaraf,

Yael Ardeli-Tzaraf

Department of Medicinal Chemistry and Natural Products, School of Pharmacy, The Hebrew University of Jerusalem, Jerusalem 91120, Israel, Fax: (+972) 2-675-7076

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Jose Manuel Perez Dr.,

Jose Manuel Perez Dr.

Departamento de Química Inorgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049-Madrid, Spain

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Elena Khazanov,

Elena Khazanov

Laboratory of Membrane and Liposome Research, Department of Biochemistry, The Hebrew University-Hadassah Medical School, Jerusalem 91120, Israel

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Yechezkel Barenholz Prof.,

Yechezkel Barenholz Prof.

Laboratory of Membrane and Liposome Research, Department of Biochemistry, The Hebrew University-Hadassah Medical School, Jerusalem 91120, Israel

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Jana Kasparkova Dr.,

Jana Kasparkova Dr.

Institute of Biophysics, Academy of Sciences of the Czech Republic, 61265 Brno, Czech Republic

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Viktor Brabec Prof.,

Viktor Brabec Prof.

Institute of Biophysics, Academy of Sciences of the Czech Republic, 61265 Brno, Czech Republic

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Dan Gibson Dr.,

Dan Gibson Dr.

[email protected]

Department of Medicinal Chemistry and Natural Products, School of Pharmacy, The Hebrew University of Jerusalem, Jerusalem 91120, Israel, Fax: (+972) 2-675-7076

Affiliated with the David R. Bloom, Center for Pharmacy at The Hebrew University of Jerusalem, Israel.

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First published: 03 May 2005

https://doi.org/10.1002/ange.200462389

Citations: 5

^†

D.G. acknowledges the partial support of the Israel Science Foundation and of the Alex Grass Center For Drug Design and Synthesis. This work was partially supported by Spanish CICYT (grant SAF2004-03111). The research of J.K. and V.B. was supported by the Grant Agency of the Academy of Sciences of the Czech Republic (Grants 5004101, B5004301) Support and sponsorship by European COSTD20/0003/00 action is gratefully acknowledged. Y.B. thanks the Belfer Foundation and the Barenholz Fund.

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Graphical Abstract

Umgehen der Cisplatinresistenz: Das trans-[PtCl₂(NH₃)(pip-pip)]⁺-Ion (siehe Struktur; rot Pt, blau N, grün Cl, grau C) ist eine cytotoxische Verbindung mit einem kationischen Piperidinopiperidin-Liganden. Der vom Pt^II-Zentrum entfernte Piperidinring ist fluktuierend und fungiert als Wasserstoffbrücken-Donor. Der Komplex bindet ohne vorherige Hydrolyse Kalbsthymus-DNA direkt und schnell (t_1/2=11 min) und umgeht die Cisplatinresistenz von Eierstockkrebszellen.

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Volume117, Issue19

May 6, 2005

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Structure and Unique Interactions with DNA of a Cationic Trans-Platinum Complex with the Nonplanar Bicyclic Piperidinopiperidine Ligand^†

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Structure and Unique Interactions with DNA of a Cationic Trans-Platinum Complex with the Nonplanar Bicyclic Piperidinopiperidine Ligand†

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Structure and Unique Interactions with DNA of a Cationic Trans-Platinum Complex with the Nonplanar Bicyclic Piperidinopiperidine Ligand^†