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| Item type: | Article | ||||
|---|---|---|---|---|---|
| Journal or Publication Title: | Journal of Medicinal Chemistry | ||||
| Publisher: | American Chemical Society | ||||
| Volume: | 48 | ||||
| Number of Issue or Book Chapter: | 23 | ||||
| Page Range: | pp. 7132-7144 | ||||
| Date: | 2005 | ||||
| Additional Information (public): | CAN 144:16568 1-6 Pharmacology 150390-77-5 Role: PAC (Pharmacological activity), THU (Therapeutic use), BIOL (Biological study), USES (Uses) (cytotoxic/estrogenic activity in breast cancer cells of platinum(II) chloro bis(fluorohydroxyphenyl)ethylenediamine complexes); 150447-56-6 Role: PAC (Pharmacological activity), THU (Therapeutic use), BIOL (Biological study), USES (Uses) (cytotoxic/estrogenic activity in breast cancer cells of platinum(II) chloro bis(fluoromethoxyphenyl)ethylenediamine complexes in comparison with analogous bis(fluorohydroxyphenyl)ethylenediamine complexes); 10025-99-7 (Dipotassium tetrachloroplatinate(2-); 149949-45-1; 149949-46-2 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of platinum(II) chloro bis(fluorohydroxyphenyl)ethylenediamine complexes); 870526-03-7P; 870526-04-8P; 870526-05-9P; 870526-06-0P; 870526-07-1P; 870526-08-2P; 870526-09-3P; 870526-10-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of platinum(II) chloro bis(fluorohydroxyphenyl)ethylenediamine complexes); 870526-01-5P; 870526-02-6P; 870623-25-9P; 870623-26-0P; 870623-27-1P; 870623-28-2P Role: PAC (Pharmacological activity), PRP (Properties), SPN (Synthetic preparation), THU (Therapeutic use), BIOL (Biological study), PREP (Preparation), USES (Uses) (prepn. of platinum(II) chloro bis(fluorohydroxyphenyl)ethylenediamine complexes and their cytotoxic/estrogenic activity in breast cancer cells) | ||||
| Institutions: | Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Schönenberger Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer) | ||||
| Projects: | SFB 234 | ||||
| Identification Number: |
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| Keywords: | Structure-activity relationship (antitumor prepn. of platinum(II) chloro bis(fluorohydroxyphenyl)ethylenediamine complexes and their cytotoxic/estrogenic activity in breast cancer cells) Antitumor agents Conformation Human Mammary gland (prepn. of platinum(II) chloro bis(fluorohydroxyphenyl)ethylenediamine complexes and their cytotoxic/estrogenic activity in breast cancer cells) Estrogen receptors Role: BSU (Biological study, unclassified), BIOL (Biological study) (prepn. of platinum(II) chloro bis(fluorohydroxyphenyl)ethylenediamine complexes and their cytotoxic/estrogenic activity in breast cancer cells) platinum chloro fluorohydroxyphenylethylenediamine prepn antitumor breast cancer | ||||
| Dewey Decimal Classification: | 500 Science > 540 Chemistry & allied sciences | ||||
| Status: | Published | ||||
| Refereed: | Yes, this version has been refereed | ||||
| Created at the University of Regensburg: | Yes | ||||
| Item ID: | 17721 |
Abstract
N-Et and N,N'-diethyl derivs. (erythro- and threo-2-PtCl2; meso- and D,L-3-PtCl2) of [meso- and D,L-1,2-bis(2,6-difluoro-3-hydroxyphenyl)ethylenediamine]dichloroplatinum(II) (meso- and D,L-1-PtCl2) were synthesized and tested for cytotoxicity on the estrogen receptor-pos. (ER+) human MCF-7 breast cancer cell line. In this test, only D,L-1-PtCl2 and threo-2-PtCl2 showed strong cytotoxic ...
Abstract
N-Et and N,N'-diethyl derivs. (erythro- and threo-2-PtCl2; meso- and D,L-3-PtCl2) of [meso- and D,L-1,2-bis(2,6-difluoro-3-hydroxyphenyl)ethylenediamine]dichloroplatinum(II) (meso- and D,L-1-PtCl2) were synthesized and tested for cytotoxicity on the estrogen receptor-pos. (ER+) human MCF-7 breast cancer cell line. In this test, only D,L-1-PtCl2 and threo-2-PtCl2 showed strong cytotoxic properties. This revealed the existence of at least one NH2 fragment as a prerequisite for antitumor activity. Also, studies on the three-dimensional structure of the new compds. demonstrated that the aryl and alkyl residues at the five-membered chelate ring have to be arranged in equatorial positions for the triggering of cytotoxic effects, very likely due to the reaction with d(GpG) sequences in DNA resulting in GG-N7,N7 chelates. A contribution of the ER-mediated processes-(a) hindrance of the cellular processing of Pt-modified DNA by overexpression of high mobility group domain proteins and (b) interruption of the vicious circle of mutual growth stimulation of breast cancer cells and granulocytes/macrophages by redn. of the formation of key cytokines-to the anti-breast cancer activity of threo-2-PtCl2 is unlikely, since the authors did not observe transcription activation in the test on ER+ MCF-7 breast cancer cells stably transfected with luciferase reporter plasmid EREwtcluc.
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