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Synthesis and antitumor activity of [1,2-bis(4-fluorophenyl)ethylenediamine][dicarboxylato]platinum(II) complexes

Gust, Ronald and Krauser, Rudolf and Schmid, Beate and Schönenberger, Helmut (1998) Synthesis and antitumor activity of [1,2-bis(4-fluorophenyl)ethylenediamine][dicarboxylato]platinum(II) complexes. Archiv der Pharmazie 331 (1), pp. 27-35.

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Abstract

The synthesis of the diastereomeric [1,2-bis(4-fluorophenyl)ethylenediamine][dicarboxylato]platinum(II) complexes, rac- and meso-4F-Pt(X) [X = oxalato (Ox), malonato (Mal), hydroxymalonato (OHMal), phenylmalonato (PhMal), tetrahydro-4H-pyran-4,4-dicarboxylato (Thpdc)], the evaluation of their structure, water soly., resistance against attack by nucleophiles, and growth inhibiting properties on the human MCF-7 breast cancer cell line are described [parent compds.: rac-4F-Pt(CBDC), and meso-4F-Pt(CBDC); ref. complexes: carboplatin, cisplatin, rac- and meso-4F-PtCl2]. The most active 4F-Pt(X) complexes, rac-4F-Pt(Mal), rac-4F-Pt(OHMal), and rac-4F-Pt(Thpdc), equal the parent compd. rac-4F-Pt(CBDC) as well as cisplatin and surpass carboplatin in their effect on the MCF-7 breast cancer cell line. Their water soly., which is of importance for an application in the cancer chemotherapy, is higher than that of rac-4F-Pt(CBDC), esp. in the case of rac-4F-Pt(OHMal) and rac-4F-Pt(Thpdc). In comparison to the dichloroplatinum(II) analog (4F-PtCl2) the stability of the 3 compds. in the presence of the strong nucleophile iodide is markedly enhanced, which means a redn. of the protein bound drug fraction in the blood and tissue compartments accompanied by an increase of the active, free drug level. The found physiochem. properties of these compds. meet the requirements for the transferability of their promising breast cancer inhibiting effects detected in cell culture expts. to in vivo conditions.

Item Type:

Article

Additional information (public):

CAN 128:162186 78-7 Inorganic Chemicals and Reactions 80-69-3 (Hydroxymalonic acid); 141-82-2 (Malonic acid); 144-62-7 (Oxalic acid); 2613-89-0 (Phenylmalonic acid); 5337-04-2 (Tetrahydro-4H-pyran-4,4-dicarboxylic acid); 184895-34-9; 185069-15-2 Role: RCT (Reactant), RACT (Reactant or reagent) (for prepn. of [1,2-bis(4-fluorophenyl)ethylenediamine][dicarboxylato]platinum(II) complexes); 7681-11-0 (Potassium iodide) Role: PEP (Physical, engineering or chemical process), PROC (Process) (kinetics of nucleophilic substitution by I- of platinum fluorophenylethylenediamine dicarboxylato complexes); 202755-80-4P; 202755-81-5P; 202755-82-6P; 202755-83-7P; 202755-84-8P Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), PRP (Properties), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (prepn., water soly., and antitumor activity against human MCF-7 breast cancer); 202646-08-0P; 202646-09-1P; 202646-10-4P; 202646-11-5P; 202646-12-6P Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), PRP (Properties), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (prepn., water soly., antitumor activity against human MCF-7 breast cancer, and kinetics of nucleophilic substitution by I-)

Institutions:

Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger
Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer)

Projects:

SFB 234

Identification Number:

Value	Type
1998:89683	Other

Keywords:

Transition metal complexes Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), PRP (Properties), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (carboxylic acid, platinum prepn., water soly., and antitumor activity against human MCF-7 breast cancer of fluorophenyl ethylenediamine dicarboxylato Pt complexes) Antitumor agents (mammary gland prepn. and antitumor activity of platinum fluorophenylethylenediamine dicarboxylato complexes) Mammary gland (neoplasm, inhibitors prepn. and antitumor activity of platinum fluorophenylethylenediamine dicarboxylato complexes) Substitution reaction kinetics (nucleophilic of platinum fluorophenylethylenediamine dicarboxylato complexes with iodide) Carboxylic acids Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), PRP (Properties), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (transition metal complexes, platinum prepn., water soly., and antitumor activity against human MCF-7 breast cancer of fluorophenyl ethylenediamine dicarboxylato Pt complexes) Solubility (water soly. of platinum fluorophenylethylenediamine dicarboxylato complexes) fluorophenylethylenediamine dicarboxylato platinum complex prepn antitumor activity platinum fluorophenylethylenediamine dicarboxylato complex soly fluorophenylethylenediamine dicarboxylato platinum complex nucleophilic substitution kinetics fluorophenylethylenediamine dicarboxylatoplatinum complex

Subjects:

500 Science > 540 Chemistry & allied sciences

Status:

Published

Refereed:

Yes, this version has been refereed

Created at the University of Regensburg:

Yes

Owner:

Petra Gürster

Deposited On:

09 Nov 2010 15:18