Synthesis, superoxide dismutase mimetic and anticancer activities of metal complexes of 2,2-dimethylpentanedioic acid(2dmepdaH2) and 3,3-dimethylpentanedioic acid(3dmepdaH2): X-ray crystal structures of [Cu(3dmepda)(bipy)]2·6H2O and [Cu(2dmepda)(bipy) (EtOH)]2·4EtOH (bipy = 2,2′bipyridine)

Michael Devereux; Malachy McCann; Denis O'Shea; Mark O'Connor; Eileen Kiely; Vickie McKee; Declan Naughton; Anna Fisher; Andrew Kellett; Maureen Walsh; Denise Egan; Carol Deegan

doi:10.1155/BCA/2006/80283

Synthesis, superoxide dismutase mimetic and anticancer activities of metal complexes of 2,2-dimethylpentanedioic acid(2dmepdaH₂) and 3,3-dimethylpentanedioic acid(3dmepdaH₂): X-ray crystal structures of [Cu(3dmepda)(bipy)]₂·6H₂O and [Cu(2dmepda)(bipy) (EtOH)]₂·4EtOH (bipy = 2,2′bipyridine)

Michael Devereux
, Malachy McCann
, Denis O'Shea
, Mark O'Connor
, Eileen Kiely
, Vickie McKee
, Declan Naughton
, Anna Fisher
, Andrew Kellett
, Maureen Walsh
, Denise Egan
, Carol Deegan

School of Chemical and BioPharmaceutical Science

Research output: Contribution to journal › Article › peer-review

Abstract

2,2-dimethylpentanedioic acid (2dmepdaH₂) and 3,3-dimethylpentanedioic acid (3dmepdaH₂) reacted with copper(II) acetate to give [Cu(2dmepda)(H₂O)₃]₂ (1) and [Cu(3dmepda)(H₂O)₃]₂ (2). Reaction of (1) and (2) with 1,10-phenanthroline and 2,2′-bipyridine yielded [Cu(2dmepda)(phen)(H₂O)]₂0.5phen (3), [Cu(2dmepda)(bipy) (H₂O)]₂ (4), [Cu(2dmepda)(bipy)(EtOH)]₂ · 2EtOH (4A), [Cu(3dmepda)(phen)(H₂O)]₂ (5), and [Cu(3dmepda)(bipy)(H₂O)]₂ · (6). The structures of (4A) and (6) each consists of a [Cu(bipy)(dicarboxylate)(solvent)]₂ dimer. The superoxide dismutase (SOD) mimetic activity of the novel copper complexes and their manganese analogues was investigated. The dimethyl sulphoxide(DMSO) soluble complexes (1)-(4) and (6) were assessed for their cancer chemotherapeutic potential towards hepatocellular carcinoma and kidney adenocarcinoma cell lines. The 1,10-phenanthroline containing complex [Cu(2dmepda)(phen)(H₂O)]₂0.5phen (3) was the most potent with activity that compares well to that of cisplatin.

Original language	English
Article number	80283
Journal	Bioinorganic Chemistry and Applications
Volume	2006
DOIs	https://doi.org/10.1155/BCA/2006/80283
Publication status	Published - 2006

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Devereux, M., McCann, M., O'Shea, D., O'Connor, M., Kiely, E., McKee, V., Naughton, D., Fisher, A., Kellett, A., Walsh, M., Egan, D., & Deegan, C. (2006). Synthesis, superoxide dismutase mimetic and anticancer activities of metal complexes of 2,2-dimethylpentanedioic acid(2dmepdaH₂) and 3,3-dimethylpentanedioic acid(3dmepdaH₂): X-ray crystal structures of [Cu(3dmepda)(bipy)]₂·6H₂O and [Cu(2dmepda)(bipy) (EtOH)]₂·4EtOH (bipy = 2,2′bipyridine). Bioinorganic Chemistry and Applications, 2006, Article 80283. https://doi.org/10.1155/BCA/2006/80283

Devereux, Michael ; McCann, Malachy ; O'Shea, Denis et al. / Synthesis, superoxide dismutase mimetic and anticancer activities of metal complexes of 2,2-dimethylpentanedioic acid(2dmepdaH₂) and 3,3-dimethylpentanedioic acid(3dmepdaH₂) : X-ray crystal structures of [Cu(3dmepda)(bipy)]₂·6H₂O and [Cu(2dmepda)(bipy) (EtOH)]₂·4EtOH (bipy = 2,2′bipyridine). In: Bioinorganic Chemistry and Applications. 2006 ; Vol. 2006.

@article{e5fe74fd93dd42329ad2cd01392c9a1f,

title = "Synthesis, superoxide dismutase mimetic and anticancer activities of metal complexes of 2,2-dimethylpentanedioic acid(2dmepdaH2) and 3,3-dimethylpentanedioic acid(3dmepdaH2): X-ray crystal structures of [Cu(3dmepda)(bipy)]2·6H2O and [Cu(2dmepda)(bipy) (EtOH)]2·4EtOH (bipy = 2,2′bipyridine)",

abstract = "2,2-dimethylpentanedioic acid (2dmepdaH2) and 3,3-dimethylpentanedioic acid (3dmepdaH2) reacted with copper(II) acetate to give [Cu(2dmepda)(H2O)3]2 (1) and [Cu(3dmepda)(H2O)3]2 (2). Reaction of (1) and (2) with 1,10-phenanthroline and 2,2′-bipyridine yielded [Cu(2dmepda)(phen)(H2O)]20.5phen (3), [Cu(2dmepda)(bipy) (H2O)]2 (4), [Cu(2dmepda)(bipy)(EtOH)]2 · 2EtOH (4A), [Cu(3dmepda)(phen)(H2O)]2 (5), and [Cu(3dmepda)(bipy)(H2O)]2 · (6). The structures of (4A) and (6) each consists of a [Cu(bipy)(dicarboxylate)(solvent)]2 dimer. The superoxide dismutase (SOD) mimetic activity of the novel copper complexes and their manganese analogues was investigated. The dimethyl sulphoxide(DMSO) soluble complexes (1)-(4) and (6) were assessed for their cancer chemotherapeutic potential towards hepatocellular carcinoma and kidney adenocarcinoma cell lines. The 1,10-phenanthroline containing complex [Cu(2dmepda)(phen)(H2O)]20.5phen (3) was the most potent with activity that compares well to that of cisplatin.",

author = "Michael Devereux and Malachy McCann and Denis O'Shea and Mark O'Connor and Eileen Kiely and Vickie McKee and Declan Naughton and Anna Fisher and Andrew Kellett and Maureen Walsh and Denise Egan and Carol Deegan",

year = "2006",

doi = "10.1155/BCA/2006/80283",

language = "English",

volume = "2006",

journal = "Bioinorganic Chemistry and Applications",

issn = "1565-3633",

publisher = "John Wiley and Sons Ltd",

}

Devereux, M, McCann, M, O'Shea, D, O'Connor, M, Kiely, E, McKee, V, Naughton, D, Fisher, A, Kellett, A, Walsh, M, Egan, D & Deegan, C 2006, 'Synthesis, superoxide dismutase mimetic and anticancer activities of metal complexes of 2,2-dimethylpentanedioic acid(2dmepdaH₂) and 3,3-dimethylpentanedioic acid(3dmepdaH₂): X-ray crystal structures of [Cu(3dmepda)(bipy)]₂·6H₂O and [Cu(2dmepda)(bipy) (EtOH)]₂·4EtOH (bipy = 2,2′bipyridine)', Bioinorganic Chemistry and Applications, vol. 2006, 80283. https://doi.org/10.1155/BCA/2006/80283

Synthesis, superoxide dismutase mimetic and anticancer activities of metal complexes of 2,2-dimethylpentanedioic acid(2dmepdaH₂) and 3,3-dimethylpentanedioic acid(3dmepdaH₂): X-ray crystal structures of [Cu(3dmepda)(bipy)]₂·6H₂O and [Cu(2dmepda)(bipy) (EtOH)]₂·4EtOH (bipy = 2,2′bipyridine). / Devereux, Michael; McCann, Malachy; O'Shea, Denis et al.
In: Bioinorganic Chemistry and Applications, Vol. 2006, 80283, 2006.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis, superoxide dismutase mimetic and anticancer activities of metal complexes of 2,2-dimethylpentanedioic acid(2dmepdaH2) and 3,3-dimethylpentanedioic acid(3dmepdaH2)

T2 - X-ray crystal structures of [Cu(3dmepda)(bipy)]2·6H2O and [Cu(2dmepda)(bipy) (EtOH)]2·4EtOH (bipy = 2,2′bipyridine)

AU - Devereux, Michael

AU - McCann, Malachy

AU - O'Shea, Denis

AU - O'Connor, Mark

AU - Kiely, Eileen

AU - McKee, Vickie

AU - Naughton, Declan

AU - Fisher, Anna

AU - Kellett, Andrew

AU - Walsh, Maureen

AU - Egan, Denise

AU - Deegan, Carol

PY - 2006

Y1 - 2006

N2 - 2,2-dimethylpentanedioic acid (2dmepdaH2) and 3,3-dimethylpentanedioic acid (3dmepdaH2) reacted with copper(II) acetate to give [Cu(2dmepda)(H2O)3]2 (1) and [Cu(3dmepda)(H2O)3]2 (2). Reaction of (1) and (2) with 1,10-phenanthroline and 2,2′-bipyridine yielded [Cu(2dmepda)(phen)(H2O)]20.5phen (3), [Cu(2dmepda)(bipy) (H2O)]2 (4), [Cu(2dmepda)(bipy)(EtOH)]2 · 2EtOH (4A), [Cu(3dmepda)(phen)(H2O)]2 (5), and [Cu(3dmepda)(bipy)(H2O)]2 · (6). The structures of (4A) and (6) each consists of a [Cu(bipy)(dicarboxylate)(solvent)]2 dimer. The superoxide dismutase (SOD) mimetic activity of the novel copper complexes and their manganese analogues was investigated. The dimethyl sulphoxide(DMSO) soluble complexes (1)-(4) and (6) were assessed for their cancer chemotherapeutic potential towards hepatocellular carcinoma and kidney adenocarcinoma cell lines. The 1,10-phenanthroline containing complex [Cu(2dmepda)(phen)(H2O)]20.5phen (3) was the most potent with activity that compares well to that of cisplatin.

AB - 2,2-dimethylpentanedioic acid (2dmepdaH2) and 3,3-dimethylpentanedioic acid (3dmepdaH2) reacted with copper(II) acetate to give [Cu(2dmepda)(H2O)3]2 (1) and [Cu(3dmepda)(H2O)3]2 (2). Reaction of (1) and (2) with 1,10-phenanthroline and 2,2′-bipyridine yielded [Cu(2dmepda)(phen)(H2O)]20.5phen (3), [Cu(2dmepda)(bipy) (H2O)]2 (4), [Cu(2dmepda)(bipy)(EtOH)]2 · 2EtOH (4A), [Cu(3dmepda)(phen)(H2O)]2 (5), and [Cu(3dmepda)(bipy)(H2O)]2 · (6). The structures of (4A) and (6) each consists of a [Cu(bipy)(dicarboxylate)(solvent)]2 dimer. The superoxide dismutase (SOD) mimetic activity of the novel copper complexes and their manganese analogues was investigated. The dimethyl sulphoxide(DMSO) soluble complexes (1)-(4) and (6) were assessed for their cancer chemotherapeutic potential towards hepatocellular carcinoma and kidney adenocarcinoma cell lines. The 1,10-phenanthroline containing complex [Cu(2dmepda)(phen)(H2O)]20.5phen (3) was the most potent with activity that compares well to that of cisplatin.

UR - https://www.scopus.com/pages/publications/33645564874

U2 - 10.1155/BCA/2006/80283

DO - 10.1155/BCA/2006/80283

M3 - Article

AN - SCOPUS:33645564874

SN - 1565-3633

VL - 2006

JO - Bioinorganic Chemistry and Applications

JF - Bioinorganic Chemistry and Applications

M1 - 80283

ER -

Devereux M, McCann M, O'Shea D, O'Connor M, Kiely E, McKee V et al. Synthesis, superoxide dismutase mimetic and anticancer activities of metal complexes of 2,2-dimethylpentanedioic acid(2dmepdaH₂) and 3,3-dimethylpentanedioic acid(3dmepdaH₂): X-ray crystal structures of [Cu(3dmepda)(bipy)]₂·6H₂O and [Cu(2dmepda)(bipy) (EtOH)]₂·4EtOH (bipy = 2,2′bipyridine). Bioinorganic Chemistry and Applications. 2006;2006:80283. doi: 10.1155/BCA/2006/80283