Metal Complexes of Biologically Important Ligands, LV Binding of Steroidal Hormones through α-Amino Acid Ligands to Platinum(II) and Palladium(II)

Abstract

A norganische C hem ie d e r U n iv ersität M ünchen, M eiserstraße 1, D-8000 M ünchen 2 D edicated to Prof. Dr. H. P. Fritz on the occasion o f his 60th birthday Z. N aturforsch. 45b, 8 1 7 -8 2 7 (1990); received N o v em b er 29, 1989 Steroid D erivatives, A m ine a n d A lcoholic C o m p o n en ts, D ichloro P latinum (II) an d P allad iu m (II) C om plexes, a-A m in o A cid A m ides an d Esters 3-(2-A m inoethoxy)estrone, 3 -(2 -am inoethoxy)estradiol, 1 7a-am inom ethylestradiol and 3-ol-17-am inoestrane react w ith co o rd in ate d activated am in o acid ligands o f p latin u m (II) and palladium (II) com plexes to give cis-a n d /ran s-C l2P t

Optimization of cisplatin for the treatment of hormone dependent tumoral diseases

“…The comparative testing of these complexes on ER + MCF-7 and ER − MDA-MB-231 breast cancer cells showed a somewhat stronger sensitivity of the former ER-containing cell line than that of the latter possessing no significant ER levels. In the ER + MCF-7 experiment, the antiproliferative effect of 10b and 10c at 1 M was comparable with that of cDDP [119]. However, it is unknown if 10b and 10c are endowed with the desired ER affinity.…”

“…Altman introduced her knowledge on amino functionalized steroids to Beck's group; they transformed such steroids into amides with activated, PtCl 2 -protected amino acids and peptides to give cis-PtCl 2 -complexes like 10a-c [119,120]. The comparative testing of these complexes on ER + MCF-7 and ER − MDA-MB-231 breast cancer cells showed a somewhat stronger sensitivity of the former ER-containing cell line than that of the latter possessing no significant ER levels.…”

Design, Synthesis, and Evaluation of ω‐(Isothiocyanato)alkylphosphinates and Phosphine Oxides as Antiproliferative Agents

“…Synthesis of (w-isothiocyanatoalkyl)diphenylphosphine oxides [29][30][31][32][33] New electrophiles-N-Boc protected w-bromoalkylamines-easily availablef rom parenta mines such as N-Boc 2-bromoethylamine( 14), [49] N-Boc 3-bromopropylamine ( 15), [50] bis-N-Boc 4-bromobutylamine (16), [51] bis-N-Boc 5-bromopentylamine (17), [52] and bis-N-Boc 6-bromohexylamine( 18) [53] were applied in the alkylation of diphenylphosphine oxide.A ll reactions were performed in pressure vials at 100 8C under microwave-assisted phase-transfer catalysis reaction (PTC) using toluene and 56 %a queousp otassium hydroxide as solvents andt etra-n-butylammonium bromide (TBABr)a sc atalyst. The protected diphenyl(w-aminoalkyl)phosphine oxides 19-23 were isolated in yields of 57-86 %a fter flash chromatography (Scheme 2).…”

Solid-state complexes of poly(L-histidine) with metal chlorides from the first row of thed-block

“…The inorganic literature of small molecules contains useful information about transition metal complexes with monomeric ␣-amino acids 13 that can be used to select polymer-metal-salt systems. cis-Diaminedichloroplatinum(II) and other related compounds are antitumor agents, 14 and cisPt(II) complexes of ␣-amino acids and their derivatives have been prepared and tested for antitumor activity. 15 Recent work has shown that amino acid esters coordinate to palladium(II) and platinum(II), 14 and the amino acids methionine and histidine coordinate to these two metal cations.…”

“…cis-Diaminedichloroplatinum(II) and other related compounds are antitumor agents, 14 and cisPt(II) complexes of ␣-amino acids and their derivatives have been prepared and tested for antitumor activity. 15 Recent work has shown that amino acid esters coordinate to palladium(II) and platinum(II), 14 and the amino acids methionine and histidine coordinate to these two metal cations. 16 Nagase et al 17 has shown that Co 2ϩ , Ni 2ϩ , and Zn 2ϩ coordinate to amino acids that contain a thiazolidine ring.…”