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Kritzenberger, J. ; Bernhardt, Günther ; Gust, Ronald ; Pistor, Petra ; Schönenberger, Helmut ; Yersin, Hartmut

Dichlorobis(cycloalkylamine)platinum(II) complexes. Structure activity relationship on the human MDA-MB-231 breast cancer cell line

Kritzenberger, J., Bernhardt, Günther, Gust, Ronald, Pistor, Petra, Schönenberger, Helmut und Yersin, Hartmut (1993) Dichlorobis(cycloalkylamine)platinum(II) complexes. Structure activity relationship on the human MDA-MB-231 breast cancer cell line. Monatshefte fuer Chemie 124 (5), S. 587-604.

Veröffentlichungsdatum dieses Volltextes: 05 Aug 2009 13:50
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.5480


Zusammenfassung

The syntheses of dichlorobis(cycloalkylamine)platinum(II) complexes with cis and trans cycloalkylamine ligands [cis-PtCl2(C3H5NH2)2 to cis-PtCl2(C8H15NH2)2 and trans-PtCl2(C7H13NH2)2 and trans-PtCl2(C8H15NH2)2 are described. The distinction between cis and trans isomers was achieved by 1H-NMR spectroscopy. The antitumor activity was detd. on the cell proliferation of the human MDA-MB-231 breast ...

The syntheses of dichlorobis(cycloalkylamine)platinum(II) complexes with cis and trans cycloalkylamine ligands [cis-PtCl2(C3H5NH2)2 to cis-PtCl2(C8H15NH2)2 and trans-PtCl2(C7H13NH2)2 and trans-PtCl2(C8H15NH2)2 are described. The distinction between cis and trans isomers was achieved by 1H-NMR spectroscopy. The antitumor activity was detd. on the cell proliferation of the human MDA-MB-231 breast cancer cell line during long-term drug exposure. The complexes with small cycloalkylamine ligands were inferior, those with large cycloalkylamine ligands were comparable or superior to cisplatin. All cycloalkylamine ligands were inactive. IR spectroscopic studies showed that the size of the cycloalkylamine ring does not lead to significant differences in the Pt-Cl binding strength. Therefore it is assumed that the markedly stronger antitumor activity of the higher homologs is not the result of a faster reaction with bionucleophiles such as DNA. A possible explanation of the high activity of some of the isomers is the strong lipophilicity of the complexes. This assumption was confirmed by toxicity tests against confluent cultures.



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Details

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftMonatshefte fuer Chemie
Band:124
Nummer des Zeitschriftenheftes oder des Kapitels:5
Seitenbereich:S. 587-604
Datum1993
Zusätzliche Informationen (Öffentlich)CAN 120:132 1-3 Pharmacology 15663-27-1 (Cisplatin) Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), THU (Therapeutic use), BIOL (Biological study), USES (Uses) (antitumor activity of, against breast cancer, dichlorobis(cycloalkylamine)platinum complexes comparison with); 38780-35-7P; 38780-36-8P; 38780-37-9P; 38780-38-0P; 41637-13-2P; 62928-48-7P; 76647-86-4P; 151767-48-5P Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), SPN (Synthetic preparation), THU (Therapeutic use), BIOL (Biological study), PREP (Preparation), USES (Uses) (prepn. and antitumor activity of, against breast cancer cells, structure in relation to); 94157-27-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction with silver nitrate and potassium chloride); 2516-34-9 (Cyclobutylamine); 5452-35-7 (Cycloheptylamine); 7681-11-0 (Potassium iodide) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with dipotassium tetrachloroplatinate); 10025-99-7 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with potassium iodide and cycloalkyl amines); 765-30-0 (Cyclopropylamine) Role: BIOL (Biological study) (reaction. of, with dipotassium tetraiodoplatinate)
InstitutionenChemie und Pharmazie > Institut für Pharmazie > Entpflichtete oder im Ruhestand befindliche Professoren > Prof. Schönenberger
Chemie und Pharmazie > Institut für Pharmazie > Lehrstuhl Pharmazeutische / Medizinische Chemie II (Prof. Buschauer)
Chemie und Pharmazie > Institut für Physikalische und Theoretische Chemie > Chair of Chemistry III - Physical Chemistry (Molecular Spectroscopy and Photochemistry) > Prof. Dr. Hartmut Yersin
Identifikationsnummer
WertTyp
1994:132Andere
10.1007/BF00819526DOI
Stichwörter / KeywordsNeoplasm inhibitors (mammary gland, dichlorobis(cycloalkylamine)platinum(II) complexes as, prepn. of, structure in relation to); Mammary gland (neoplasm, inhibitors, dichlorobis(cycloalkylamine)platinum(II) complexes as, prepn. of, structure in relation to); Molecular structure-biological activity relationship (neoplasm-inhibiting, of dichlorobis(cycloalkylamine)platinum(II) complexes); dichlorobiscycloalkylamineplatinum antitumor prepn structure; biscycloalkylamineplatinum dichloro antitumor prepn structure; platinum cycloalkylamine chloro antitumor prepn structure
Dewey-Dezimal-Klassifikation500 Naturwissenschaften und Mathematik > 570 Biowissenschaften, Biologie
500 Naturwissenschaften und Mathematik > 540 Chemie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenJa
URN der UB Regensburgurn:nbn:de:bvb:355-epub-54807
Dokumenten-ID5480

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