Synthesis and antiproliferative activity of a series of new platinum and palladium diphosphane complexes

Carleen Cullinane, Glen B. Deacon, Penny R. Drago, Anja P. Erven, Peter C. Junk, Jenny Luu, Gerd Meyer, Simon Schmitz, Ingo Ott, Julia Schur, Lorraine K. Webster, Axel Klein

Research output: Contribution to journalArticleResearchpeer-review

Abstract

New organometallic complexes [M(dppe)(R)2] {where M = Pt or Pd, dppe = 1,2-bis(diphenylphosphano)ethane, and R = C6F4H-x (x = 6,5,4), C6F3H2-3,5, C6F3H2-5,6, C6F3H2-3,6, C6F4(OMe)-4, and C6F4(cyclo-C5H10N)-4, the numbers x refer to the positions of the protons in the polyfluoroaryl ligands} were synthesised either through transmetalation from the dichlorido complexes [M(dppe)Cl2] or through ligand exchange using [M(diene)Cl2] precursor complexes with diene = 1,5-cyclooctadiene (cod) or 1,5-hexadiene (hex). Alternatively, [M(dppX)Cl(R)] complexes with dppX = dppm (1,1-bis(diphenylphosphano)methane), dppe, dppp (1,3-bis(diphenylphosphano)propane), and dppb (1,4-bis(diphenylphosphano)butane) were prepared in decarboxylation reactions from thallium(i) carboxylates Tl(O2CR). The different preparative methods were compared in terms of yield and purity. Structural and spectroscopic data are reported for the new dppX- and diene-M(R)2 complexes. Antiproliferative activity was investigated for these new complexes against the HT-29 (colon carcinoma) and MCF-7 (breast adenocarcinoma) cell lines, and the active compounds of this first series together with organometallic dppX or hex PtII or PdII complexes were then included in cell tests using L1210 (leukaemia cells) and the cisplatin-resistant L1210/DDP cell line. Remarkably, promising antiproliferative results were found for a few PtII and PdII complexes, while structurally closely related compounds were essentially nontoxic.

Original languageEnglish
Pages (from-to)1918-1932
Number of pages15
JournalDalton Transactions
Volume47
Issue number6
DOIs
Publication statusPublished - 1 Jan 2018

Cite this

Cullinane, Carleen ; Deacon, Glen B. ; Drago, Penny R. ; Erven, Anja P. ; Junk, Peter C. ; Luu, Jenny ; Meyer, Gerd ; Schmitz, Simon ; Ott, Ingo ; Schur, Julia ; Webster, Lorraine K. ; Klein, Axel. / Synthesis and antiproliferative activity of a series of new platinum and palladium diphosphane complexes. In: Dalton Transactions. 2018 ; Vol. 47, No. 6. pp. 1918-1932.
@article{818b9106ccc04647878edeb4f87b5ab8,
title = "Synthesis and antiproliferative activity of a series of new platinum and palladium diphosphane complexes",
abstract = "New organometallic complexes [M(dppe)(R)2] {where M = Pt or Pd, dppe = 1,2-bis(diphenylphosphano)ethane, and R = C6F4H-x (x = 6,5,4), C6F3H2-3,5, C6F3H2-5,6, C6F3H2-3,6, C6F4(OMe)-4, and C6F4(cyclo-C5H10N)-4, the numbers x refer to the positions of the protons in the polyfluoroaryl ligands} were synthesised either through transmetalation from the dichlorido complexes [M(dppe)Cl2] or through ligand exchange using [M(diene)Cl2] precursor complexes with diene = 1,5-cyclooctadiene (cod) or 1,5-hexadiene (hex). Alternatively, [M(dppX)Cl(R)] complexes with dppX = dppm (1,1-bis(diphenylphosphano)methane), dppe, dppp (1,3-bis(diphenylphosphano)propane), and dppb (1,4-bis(diphenylphosphano)butane) were prepared in decarboxylation reactions from thallium(i) carboxylates Tl(O2CR). The different preparative methods were compared in terms of yield and purity. Structural and spectroscopic data are reported for the new dppX- and diene-M(R)2 complexes. Antiproliferative activity was investigated for these new complexes against the HT-29 (colon carcinoma) and MCF-7 (breast adenocarcinoma) cell lines, and the active compounds of this first series together with organometallic dppX or hex PtII or PdII complexes were then included in cell tests using L1210 (leukaemia cells) and the cisplatin-resistant L1210/DDP cell line. Remarkably, promising antiproliferative results were found for a few PtII and PdII complexes, while structurally closely related compounds were essentially nontoxic.",
author = "Carleen Cullinane and Deacon, {Glen B.} and Drago, {Penny R.} and Erven, {Anja P.} and Junk, {Peter C.} and Jenny Luu and Gerd Meyer and Simon Schmitz and Ingo Ott and Julia Schur and Webster, {Lorraine K.} and Axel Klein",
year = "2018",
month = "1",
day = "1",
doi = "10.1039/c7dt04615d",
language = "English",
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pages = "1918--1932",
journal = "Journal of the Chemical Society. Dalton Transactions",
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Cullinane, C, Deacon, GB, Drago, PR, Erven, AP, Junk, PC, Luu, J, Meyer, G, Schmitz, S, Ott, I, Schur, J, Webster, LK & Klein, A 2018, 'Synthesis and antiproliferative activity of a series of new platinum and palladium diphosphane complexes' Dalton Transactions, vol. 47, no. 6, pp. 1918-1932. https://doi.org/10.1039/c7dt04615d

Synthesis and antiproliferative activity of a series of new platinum and palladium diphosphane complexes. / Cullinane, Carleen; Deacon, Glen B.; Drago, Penny R.; Erven, Anja P.; Junk, Peter C.; Luu, Jenny; Meyer, Gerd; Schmitz, Simon; Ott, Ingo; Schur, Julia; Webster, Lorraine K.; Klein, Axel.

In: Dalton Transactions, Vol. 47, No. 6, 01.01.2018, p. 1918-1932.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Synthesis and antiproliferative activity of a series of new platinum and palladium diphosphane complexes

AU - Cullinane, Carleen

AU - Deacon, Glen B.

AU - Drago, Penny R.

AU - Erven, Anja P.

AU - Junk, Peter C.

AU - Luu, Jenny

AU - Meyer, Gerd

AU - Schmitz, Simon

AU - Ott, Ingo

AU - Schur, Julia

AU - Webster, Lorraine K.

AU - Klein, Axel

PY - 2018/1/1

Y1 - 2018/1/1

N2 - New organometallic complexes [M(dppe)(R)2] {where M = Pt or Pd, dppe = 1,2-bis(diphenylphosphano)ethane, and R = C6F4H-x (x = 6,5,4), C6F3H2-3,5, C6F3H2-5,6, C6F3H2-3,6, C6F4(OMe)-4, and C6F4(cyclo-C5H10N)-4, the numbers x refer to the positions of the protons in the polyfluoroaryl ligands} were synthesised either through transmetalation from the dichlorido complexes [M(dppe)Cl2] or through ligand exchange using [M(diene)Cl2] precursor complexes with diene = 1,5-cyclooctadiene (cod) or 1,5-hexadiene (hex). Alternatively, [M(dppX)Cl(R)] complexes with dppX = dppm (1,1-bis(diphenylphosphano)methane), dppe, dppp (1,3-bis(diphenylphosphano)propane), and dppb (1,4-bis(diphenylphosphano)butane) were prepared in decarboxylation reactions from thallium(i) carboxylates Tl(O2CR). The different preparative methods were compared in terms of yield and purity. Structural and spectroscopic data are reported for the new dppX- and diene-M(R)2 complexes. Antiproliferative activity was investigated for these new complexes against the HT-29 (colon carcinoma) and MCF-7 (breast adenocarcinoma) cell lines, and the active compounds of this first series together with organometallic dppX or hex PtII or PdII complexes were then included in cell tests using L1210 (leukaemia cells) and the cisplatin-resistant L1210/DDP cell line. Remarkably, promising antiproliferative results were found for a few PtII and PdII complexes, while structurally closely related compounds were essentially nontoxic.

AB - New organometallic complexes [M(dppe)(R)2] {where M = Pt or Pd, dppe = 1,2-bis(diphenylphosphano)ethane, and R = C6F4H-x (x = 6,5,4), C6F3H2-3,5, C6F3H2-5,6, C6F3H2-3,6, C6F4(OMe)-4, and C6F4(cyclo-C5H10N)-4, the numbers x refer to the positions of the protons in the polyfluoroaryl ligands} were synthesised either through transmetalation from the dichlorido complexes [M(dppe)Cl2] or through ligand exchange using [M(diene)Cl2] precursor complexes with diene = 1,5-cyclooctadiene (cod) or 1,5-hexadiene (hex). Alternatively, [M(dppX)Cl(R)] complexes with dppX = dppm (1,1-bis(diphenylphosphano)methane), dppe, dppp (1,3-bis(diphenylphosphano)propane), and dppb (1,4-bis(diphenylphosphano)butane) were prepared in decarboxylation reactions from thallium(i) carboxylates Tl(O2CR). The different preparative methods were compared in terms of yield and purity. Structural and spectroscopic data are reported for the new dppX- and diene-M(R)2 complexes. Antiproliferative activity was investigated for these new complexes against the HT-29 (colon carcinoma) and MCF-7 (breast adenocarcinoma) cell lines, and the active compounds of this first series together with organometallic dppX or hex PtII or PdII complexes were then included in cell tests using L1210 (leukaemia cells) and the cisplatin-resistant L1210/DDP cell line. Remarkably, promising antiproliferative results were found for a few PtII and PdII complexes, while structurally closely related compounds were essentially nontoxic.

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U2 - 10.1039/c7dt04615d

DO - 10.1039/c7dt04615d

M3 - Article

VL - 47

SP - 1918

EP - 1932

JO - Journal of the Chemical Society. Dalton Transactions

JF - Journal of the Chemical Society. Dalton Transactions

SN - 1477-9226

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