Dichloro[1,2-bis(4-hydroxyphenyl)ethylenediamine]platinum(II) complexes: an approach to develop compounds with a specific effect on the hormone-dependent mammary carcinoma

Wappes, B.; Jennerwein, Margaretha; Angerer, E. von; Schönenberger, Helmut; Engel, Jürgen; Berger, Martin R.; Wrobel, Karl‐Heinz

doi:10.1021/jm00376a009

Cited by 52 publications

(20 citation statements)

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“…The first compounds of this sort to be prepared, a series of seteroisomers of dichloro[1,2-bis(4-hydroxyphenyl)ethylenediamine]platinum(II), competed with estrogen for interaction with the ER, but were toxic to ER+ and ER− cells alike. 127 Subsequent substitution at the 2 and 6 positions of the two phenyl rings with chlorine atoms, a substitution that had been shown to increase the affinity of the ligand for the ER, 128 produced a set of complexes that not only interacted with the ER but also selectively killed ER+ mammary carcinoma cells. 129 Variations on the substitutions of the nitrogen atoms and ring carbon atoms can influence estrogenicity and cytotoxicity, but often in a mutually exclusive manner.…”

Section: Platinum(ii) Compounds With a Mechanism Of Action Similarmentioning

confidence: 99%

The Next Generation of Platinum Drugs: Targeted Pt(II) Agents, Nanoparticle Delivery, and Pt(IV) Prodrugs

2016

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The platinum drugs, cisplatin, carboplatin, and oxaliplatin, prevail in the treatment of cancer,, but new platinum agents have been very slow to enter the clinic. Recently, however, there has been a surge of activity, based on a great deal of mechanistic information, aimed at developing non-classical platinum complexes that operate via mechanisms of action distinct from those of the approved drugs. The use of nanodelivery devices has also grown and many different strategies have been explored to incorporate platinum warheads into nanomedicine constructs. In this review, we discuss these efforts to create the next generation of platinum anticancer drugs. The introduction provides the reader with a brief overview of the use, development, and mechanism of action of the approved platinum drugs to provide the context in which more recent research has flourished. We then describe approaches that explore non-classical platinum(II) complexes with trans geometry and with a monofunctional coordination mode, polynuclear platinum(II) compounds, platinum(IV) prodrugs, dual-treat agents, and photoactivatable platinum(IV) complexes. Nanodelivery particles designed to deliver platinum(IV) complexes will also be discussed, including carbon nanotubes, carbon nanoparticles, gold nanoparticles, quantum dots, upconversion nanoparticles, and polymeric micelles. Additional nanoformulations including supramolecular self-assembled structures, proteins, peptides, metal-organic frameworks, and coordination polymers will then be described. Finally, the significant clinical progress made by nanoparticle formulations of platinum(II) agents will be reviewed. We anticipate that such a synthesis of disparate research efforts will not only help to generate new drug development ideas and strategies, but also reflect our optimism that the next generation of platinum cancer drugs is about to arrive.

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Section: Platinum(ii) Compounds With a Mechanism Of Action Similarmentioning

confidence: 99%

The Next Generation of Platinum Drugs: Targeted Pt(II) Agents, Nanoparticle Delivery, and Pt(IV) Prodrugs

2016

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“…The stereoselectivity was similar to that observed with breast cancer cells: This study was a continuation of our attempts to optimize the antitumor activity of [S,S/R,R-1,2-diamino-1,2-bis(4-fluorophenyl)ethane]dichloroplatinum(II) ((R,R/S,S)-4F-Ph/4-Ph-PtCl 2 ). (R,R/S,S)-4F-Ph/4-Ph-PtCl 2 showed high activity in vitro and in vivo against a wide range of murine tumors, [7,8] and was more active than cisplatin and its R,S/S,R-configured diastereomeric congener. The attempt to optimize the antitumor activity of (R,R/S,S)-4F-Ph/4-Ph-PtCl 2 failed because of a separation of enantiomers.…”

Section: Structural Characterizationmentioning

confidence: 98%

“…[7,8] However, the attempt failed to increase the antiproliferative effects by separation into enantiomerically pure compounds. [9] In an earlier study, we demonstrated the increase of in vitro cytotoxicity by the exchange of one 4-fluorophenyl residue with a methyl (4F-Ph/Me-PtCl 2 ), ethyl (4F-Ph/Et-PtCl 2 ) or propyl group (4F-Ph/ Prop-PtCl 2 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Cytotoxicity of Enantiomerically Pure [1,2‐Diamino‐1‐(4‐fluorophenyl)‐3‐methylbutane]platinum(II) Complexes

et al. 2006

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A series of leaving group derivatives of enantiomerically pure [1,2‐diamino‐1‐(4‐fluorophenyl)‐3‐methylbutane]platinum(II) complexes were synthesized and tested for cytotoxicity. The enantiomeric purity was determined by 1H NMR spectroscopy on the final diamines after derivation with (1R)‐myrtenal. For coordination to platinum, the diamines were reacted with K2PtI4. The treatment of diiodoplatinum(II) complexes (4F‐Ph/iProp‐PtI2) with Ag2SO4 resulted in the sulfatoplatinum(II) complexes (4F‐Ph/iProp‐PtSO4), which can be easily transformed to dichloroplatinum(II) complexes (4F‐Ph/iProp‐PtCl2) with 2 n HCl. The importance of the leaving groups and the configuration at the diamine ligand on the antiproliferative effects was evaluated on the hormone‐dependent MCF‐7 and the hormone‐independent MDA‐MB 231 breast cancer cell lines as well as the LNCaP/FGC prostate cancer cell line. (R,R)‐4F‐Ph/iProp‐PtCl2 was identified as the most active platinum(II) complex. The 3‐methyl group increased antiproliferative effects relative to the [1,2‐diamino‐1‐(4‐fluorophenyl)butane]platinum(II) complexes described in an earlier study.

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“…Schonenberger and co-authors have reported upon the ability of ethylenediamine derivatives and their Pt(II) complexes to bind to estrogen receptors, being active against hormone-dependent mammary carcinoma resistant to cisplatin (25)(26)(27)(28)(29).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, and Cytotoxic Activity of Novel Platinum(II) Complexes Derived from N‐Benzyl‐Ethylenediamine and Oxalate

et al. 2010

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This work describes the synthesis and characterization of three novel complexes derived from Nbenzyl-ethylenediamine and oxalate. Precursor compounds were synthesized by reacting N-benzyl-ethylenediamine with K 2 PtCl 4 . Subsequent substitution of chlorides by oxalate led to the final products. Elemental analysis and the infrared, 1 H, 13 C, and 195 Pt NMR spectra of these complexes were provided. The cytotoxic activities were investigated against human non-small cell lung carcinoma (A 549 ), mouse non-metastatic cell skin melanoma (B16-F1), mouse metastatic cell skin melanoma (B16-F10), human cell breast adenocarcinoma (MDA-MB-231) and normal cell lines such as baby hamster cell kidney (BHK-21), hamster cell ovary (CHO) and compared to cisplatin and carboplatin under the same experimental conditions. The presence of oxalate as a leaving group conferred an interesting cytotoxicity profile to the complexes in the tested cell lines.

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Dichloro[1,2-bis(4-hydroxyphenyl)ethylenediamine]platinum(II) complexes: an approach to develop compounds with a specific effect on the hormone-dependent mammary carcinoma

Cited by 52 publications

References 1 publication

The Next Generation of Platinum Drugs: Targeted Pt(II) Agents, Nanoparticle Delivery, and Pt(IV) Prodrugs

The Next Generation of Platinum Drugs: Targeted Pt(II) Agents, Nanoparticle Delivery, and Pt(IV) Prodrugs

Synthesis and Cytotoxicity of Enantiomerically Pure [1,2‐Diamino‐1‐(4‐fluorophenyl)‐3‐methylbutane]platinum(II) Complexes

Synthesis, Characterization, and Cytotoxic Activity of Novel Platinum(II) Complexes Derived from N‐Benzyl‐Ethylenediamine and Oxalate

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