Cisplatin analogues with 2,2′-dipyridylamine ligands and their reactions with DNA model nucleobases

Rauterkus, Michael J.; Fakih, Sarah; Mock, Christian; Puscasu, Ina; Krebs, Bernt

doi:10.1016/s0020-1693(02)01540-2

Cited by 71 publications

(27 citation statements)

References 28 publications

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“…The ligands of 2,2-dipyridylamine and derivatives thereof have an affinity for various transition metals such as platinum [4],iron [5], palladium [6] and avariety of others [7][8]. The interest in these ligands and complexes thereof, is due to their potential applications as anti-cancer agents [9][10] and catalysts [11][12][13].T he dichloro-N,N-bis(pyridine-2-ylmethyl)cyclohexamino copper(II) (Figure 1) complex crystallized in the monoclinic space group P2 1 /c ,with four molecules per unit cell. Thus the asymmetric unit consists of aCu(II) atom coordinated to one tridentate N,N-bis(pyridine-2-ylmethyl)cyclohexamino ligand and two chlorine atomstoform adistorted trigonal bipyramid.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of dichloro-N,N-bis(pyridine-2-ylmethyl)cyclohexamino copper(II), C18H23Cl2CuN3

Mphure

Visser

Roodt

et al. 2015

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Discussionmentioning

confidence: 99%

Crystal structure of dichloro-N,N-bis(pyridine-2-ylmethyl)cyclohexamino copper(II), C18H23Cl2CuN3

Mphure

Visser

Roodt

et al. 2015

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Three mononuclear cis ‐Pt(II) complexes, viz . [Pt{2‐(phenylthiomethyl)quinoline}Cl 2 ], Pt(L1)Cl 2 , [Pt{2‐(4‐ tert ‐butylthiophenol)quinoline}Cl 2 ], Pt(L2)Cl 2 , and [Pt{2‐(4‐fluorothiophenol)quinoline}Cl 2 ], Pt(L3)Cl 2 , were synthesized by reacting 1 equiv of the respective thioether ligand with K 2 PtCl 4 (0.46 g, 0.9 mmol) according to a literature method …”

Section: Methodsmentioning

confidence: 99%

Reactivity of cis‐platinum(II) complexes with 2‐(4‐substituted)phenylthiomethyl)quinoline nonleaving ligands toward thiourea nucleophiles

Mthiyane

Mambanda

Jaganyi

2018

Int J of Chemical Kinetics

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The sequential substitution of aqua ligands from quinoline}(H 2 O) 2 ]CF 3 SO 3 , Pt(L1), [Pt{2-(4-tert-butylphenylthiomethyl)quinoline}(H 2 O) 2 ]CF 3 SO 3 Pt(L2), and [Pt{2-(4-fluorophenylthiomethyl) quinoline}(H 2 O) 2 ]CF 3 SO 3 Pt(L3) by thiourea nucleophiles (Nu) was studiedunder pseudo-first-order conditions as a function of concentration and temperature using stopped-flow and UV-visible spectrophotometric techniques. The observed pseudo-first-order rate constants for the substitutions can be described by the rate law: k obs(1/2) = k 2(1/2) [Nu], where the subscript denotes the consecutive substitution steps. The first aqua ligand was substituted opposite to the strong -trans-directing thioether followed by the aqua ligand opposite to the quinoline or pyridine moieties. Second-order rate constants, k 2(1st) , for the substitution of the first aqua ligand by thiourea nucleophiles ranged between 9 and 22 M −1 s −1 for Pt(L1), 86 and 326 M −1 s −1 for Pt(L2), and 58 -287 M −1 s −1 for Pt(L3). The ranges of the second-order rate constant, k 2(2nd) , were always lower than the k 2(1st) 's and are 0.3-9 M −1 s -1 for Pt(L1), 2-20 M −1 s −1 for Pt(L2), and 0.3-5 M −1 s −1 for Pt(L3). Aqua substitution from Pt(L2) is slower for both steps than from Pt4, its pyridyl derivative from our previous study. A Job's method of continuous variation plot suggests a species with a metal-to-nucleophile ratio of 1:3 as the ultimate product of the chloride substitution from the Pt(II) complexes by the incoming thiourea nucleophiles. The high and negative activation entropy and low and positive activation enthalpy values support an associative mechanism of activation, characteristic of substitution reactions occurring in square-planar complexes. K E Y W O R D Sassociative mechanism, consecutive reaction, Pt(II) mononuclear complexes, substitution Int J Chem Kinet. 2018;50:531-543.

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“…[21] The C, H, N elemental analyses were performed with a Hewlett-Packard 185B carbon-hydrogen-nitrogen analyzer. The [PtI 2 (dpa)] complex was synthesized in accord with a previously published procedure.…”

Section: Methodsmentioning

confidence: 99%

“…Structural refinements were performed with SHELXL-97. The crystallographic details are summarized in Table S1 2 : AgOTf (0.177 g, 0.69 mmol) was added to a suspension of [PtI 2 (dpa)] [21] (0.186 g, 0.30 mmol) in RCN (R = Me, Et, Ph, PhCH 2 ; 5.0 mL), and the mixture was vigorously stirred in the dark at room temp. Other hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms with d(C-H) = 0.95-1.00 Å and U iso = 1.2-1.5U eq (parent atom).…”

Section: Methodsmentioning

confidence: 99%

Phosphorescent Pt^II Systems Featuring Both 2,2′‐Dipyridylamine and 1,3,5‐Triazapentadiene Ligands

et al. 2014

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The treatment of cis- [Pt(dpa)(RCN) 2 ][SO 3 CF 3 ] 2 {dpa = 2,2Јdipyridylamine, R = Me, Et, CH 2 Ph, Ph; [2a-d](OTf) 2 } (OTf = SO 3 CF 3 ) with 2 equiv. of N,NЈ-diphenylguanidine [NH=C-(NHPh) 2 ] in CH 2 Cl 2 solutions at room temp. for 16 h gives [Pt(dpa){NH=C(R)NC(NHPh)=NPh}][SO 3 CF 3 ] {[3a,b,d](OTf)} as the addition products and [Pt(dpa){NH=C(R)NHC(R)= NH}][SO 3 CF 3 ] 2 {[4a,b](OTf) 2 } as the tailoring products. The formulation of complexes [3a,b,d](OTf) and [4a,b](OTf) 2 was supported by satisfactory C, H, and N elemental analyses and agreeable high-resolution ESI-MS, IR, and 1 H (in-[a] Institute

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Cisplatin analogues with 2,2′-dipyridylamine ligands and their reactions with DNA model nucleobases

Cited by 71 publications

References 28 publications

Crystal structure of dichloro-N,N-bis(pyridine-2-ylmethyl)cyclohexamino copper(II), C18H23Cl2CuN3

Crystal structure of dichloro-N,N-bis(pyridine-2-ylmethyl)cyclohexamino copper(II), C18H23Cl2CuN3

Reactivity of cis‐platinum(II) complexes with 2‐(4‐substituted)phenylthiomethyl)quinoline nonleaving ligands toward thiourea nucleophiles

Phosphorescent Pt^II Systems Featuring Both 2,2′‐Dipyridylamine and 1,3,5‐Triazapentadiene Ligands

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Cisplatin analogues with 2,2′-dipyridylamine ligands and their reactions with DNA model nucleobases

Cited by 71 publications

References 28 publications

Crystal structure of dichloro-N,N-bis(pyridine-2-ylmethyl)cyclohexamino copper(II), C18H23Cl2CuN3

Crystal structure of dichloro-N,N-bis(pyridine-2-ylmethyl)cyclohexamino copper(II), C18H23Cl2CuN3

Reactivity of cis‐platinum(II) complexes with 2‐(4‐substituted)phenylthiomethyl)quinoline nonleaving ligands toward thiourea nucleophiles

Phosphorescent PtII Systems Featuring Both 2,2′‐Dipyridylamine and 1,3,5‐Triazapentadiene Ligands

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Phosphorescent Pt^II Systems Featuring Both 2,2′‐Dipyridylamine and 1,3,5‐Triazapentadiene Ligands