Interaction of cis-pt(ino)2Cl2 with amino acids

Garoufis, Achilleas; Haran, R.; Pasdeloup, Maurice; Laussac, Jean‐Pierre; Hadjiliadis, Nick

doi:10.1016/0162-0134(87)85006-7

Cited by 20 publications

(6 citation statements)

References 38 publications

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“…1 H NMR: δ ) 3.54 (t, 2H, CH2, 2 J(HH) ) 6.1 Hz), 3.99 (s, 2H, CH 2), and 5.26 (b, 2H, NH2). 13 13 C (67.80MHz)). 98% 15 N-enriched samples were used in the 15 N NMR measurement.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR: δ ) 3.54 (t, 2H, CH2, 2 J(HH) ) 6.1 Hz), 3.99 (s, 2H, CH 2), and 5.26 (b, 2H, NH2). 13 C NMR: δ ) 49.74 (CH 2), 51.41 (CH2), 178.20 (CdO), and 187.62 (COO). 195 Pt NMR: δ ) -2152.…”

Section: Methodsmentioning

confidence: 99%

“…98% 15 N-enriched samples were used in the 15 N NMR measurement. All of the 15 N, 195 Pt, and, 13 C NMR spectra were proton-decoupled in D2O. 15 N NMR spectra were externally referenced to the saturated 15 NH4Cl solution (δ NH4 + is 27.34 ppm relative to δNH3 ()0 ppm)), and 195 Pt spectra were externally referenced to K 2PtCl4 (from Na2PtCl6 in D2O,δPt for K2PtCl4 -1622 ppm).…”

Section: Methodsmentioning

confidence: 99%

“…The major difficulty in studying platinum complexes containing peptides is their kinetic inertness, that is to say, peptide complexes of platinum are nonlabile species − In a few cases analytical data and/or X-ray crystal data 16,17 have been reported. It is important to isolate the peptide platinum complexes and to know their chemical and chemotherapeutic properties.…”

Section: Introductionmentioning

confidence: 99%

“…12 Reactions of platinum(II) with oligopeptides have produced several species in all cases, and most of them have been studied only in solution. [13][14][15] In a few cases analytical data and/or X-ray crystal data 16,17 It is important to isolate the peptide platinum complexes and to know their chemical and chemotherapeutic properties. Deprotonation of the peptide amide NH is indirectly measured by titration and elemental analysis, except for one report which showed the deprotonation of the peptide amide NH by using X-ray and neutron diffraction of the crystal structure of [Pt(glymet)Cl] -, where H 2 glymet indicates glycylmethionine, showing that the amine nitrogen, the peptide nitrogen, and the thioether sulfur are coordinated to the metal.…”

Section: Introductionmentioning

confidence: 99%

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Platinum(II) Complexes with Diglycine: X-ray Crystal Structure,¹⁵N NMR Spectra, and Growth-Inhibitory Activity against Mouse Meth A Solid Tumor in Vivo

et al. 1997

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Two new dipeptide complexes of the form H[Pt(digly)Cl] (2) (H2digly = glycylglycine) and H[Pt(Hdigly)Cl2] (4) were newly prepared, and K[Pt(Hdigly)Cl2] (3) was isolated. Complex 1, K[Pt(digly)Cl], crystallizes in the monoclinic space group C2/c with unit cell dimensions a = 25.77(1) Å, b = 4.09(2) Å, c = 16.432(9) Å, β = 103.74(4)°, and Z = 8. Complex 3 crystallizes in the monoclinic space group P21/c with unit cell dimensions a = 8.892(5) Å, b = 11.387(4) Å, c = 9.974(4) Å, β = 105.45(4)°, Z = 4. Complex 4 crystallizes in the monoclinic space group P21/c with unit cell dimensions a = 9.311(6) Å, b = 7.737(8), c = 15.627(4) Å, β = 105.92(3)°, Z = 4. Complex 4 has the rare iminol type H2digly coordinating to Pt. The 15N chemical shifts and the coupling constants of the deprotonated coordinated amide N were obtained for the first time for these complexes. These amide peaks showed almost no coordination shift compared with the large coordination shift of the amine nitrogen. The coupling constants between Pt and deprotonated nitrogen for K[Pt(Hdipep)Cl2] were larger than those for K[Pt(dipep)Cl]. The growth inhibition assays of K[Pt(digly)Cl], K[Pt(Hdigly)Cl2], and cis-diamminedichloroplatinum(II) (cisplatin) against methylcholanthrene-induced Meth A fibrosarcoma (Meth A) solid tumor transplanted in BALB/c mice were measured. In mice, 35.9% of slight growth inhibition was observed in the group administered with K[Pt(digly)Cl] (dose of 26 mg/kg/day), and 40.6% in the group administered with K[Pt(Hdigly)Cl2] (dose of 52 mg/kg/day), and 45.3% cisplatin (dose of 10 mg/kg/day). The side effects related to the decrease in body weight are milder than that of cisplatin. Their toxicity against normal mouse bone marrow cells was measured. All of them exhibited toxicity against bone marrow cells, but K[Pt(digly)Cl] and K[Pt(Hdigly)Cl2] had only 1/10 the toxicity of cisplatin.

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“…1 H NMR: δ ) 3.54 (t, 2H, CH2, 2 J(HH) ) 6.1 Hz), 3.99 (s, 2H, CH 2), and 5.26 (b, 2H, NH2). 13 13 C (67.80MHz)). 98% 15 N-enriched samples were used in the 15 N NMR measurement.…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Platinum(II) Complexes with Diglycine: X-ray Crystal Structure,¹⁵N NMR Spectra, and Growth-Inhibitory Activity against Mouse Meth A Solid Tumor in Vivo

et al. 1997

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Coordination complexes of l-azetidine-2-carboxylic acid with platinum(II) and palladium(II)

Voureka

Tsangaris

Terzis

et al. 1996

Transition Met Chem

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The complexes K[Pt(L-aze)C12, [Pt(L-aze)21 and [Pd(Laze)z ] (L-aze = L-azetidine-2-carboxylate) were prepared. X-ray structures show that [Pt(L-aze)e ] and [Pd(L-aze)e ] are isomorphous, having a planar tetragonal geometry with a trans configuration around the Pt and Pd atoms. Slight puckerings of the MN(1)N(11)O(11) chelate ring (M = Pt or Pd) and the azetidine ring were observed. The circular dichroism (c.d.) spectra of the complexes in aqueous solution agree with the structures found in the solid state as far as the hexadecant rule is concerned, giving, for the trans configuration of [M(L-ia)21 (where ia = imino acid), the profile of the c.d. signs for the three predominant d-d transitions as: +, -, -. I.r., conductivity and n.m.r. measurements are also reported and are in accord with the proposed structures.

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Complex compounds of platinum (II) and (IV) with amino acids, peptides and their derivatives

Iakovidis

Hadjiliadis

1994

Coordination Chemistry Reviews

106

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Interaction of cis-pt(ino)2Cl2 with amino acids

Cited by 20 publications

References 38 publications

Platinum(II) Complexes with Diglycine: X-ray Crystal Structure,¹⁵N NMR Spectra, and Growth-Inhibitory Activity against Mouse Meth A Solid Tumor in Vivo

Platinum(II) Complexes with Diglycine: X-ray Crystal Structure,¹⁵N NMR Spectra, and Growth-Inhibitory Activity against Mouse Meth A Solid Tumor in Vivo

Coordination complexes of l-azetidine-2-carboxylic acid with platinum(II) and palladium(II)

Complex compounds of platinum (II) and (IV) with amino acids, peptides and their derivatives

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Interaction of cis-pt(ino)2Cl2 with amino acids

Cited by 20 publications

References 38 publications

Platinum(II) Complexes with Diglycine: X-ray Crystal Structure,15N NMR Spectra, and Growth-Inhibitory Activity against Mouse Meth A Solid Tumor in Vivo

Platinum(II) Complexes with Diglycine: X-ray Crystal Structure,15N NMR Spectra, and Growth-Inhibitory Activity against Mouse Meth A Solid Tumor in Vivo

Coordination complexes of l-azetidine-2-carboxylic acid with platinum(II) and palladium(II)

Complex compounds of platinum (II) and (IV) with amino acids, peptides and their derivatives

Contact Info

Product

Resources

About

Platinum(II) Complexes with Diglycine: X-ray Crystal Structure,¹⁵N NMR Spectra, and Growth-Inhibitory Activity against Mouse Meth A Solid Tumor in Vivo

Platinum(II) Complexes with Diglycine: X-ray Crystal Structure,¹⁵N NMR Spectra, and Growth-Inhibitory Activity against Mouse Meth A Solid Tumor in Vivo