Copper (II) complexes possessing alkyl-substituted polypyridyl ligands: Structural characterization and in vitro antitumor activity
In an effort to find alternatives to the antitumor drug cisplatin, a series of copper (II) complexes possessing alkyl-substituted polypyridyl ligands have been synthesized. Eight new complexes are reported herein: μ-dichloro-bis{2,9-di-sec-butyl-1,10-phenanthrolinechlorocopper(II)} {[(di-sec-butylph...
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Published in | Journal of inorganic biochemistry Vol. 166; pp. 12 - 25 |
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Main Authors | , , , , , , , , , , |
Format | Journal Article |
Language | English |
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United States
Elsevier Inc
01.01.2017
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Abstract | In an effort to find alternatives to the antitumor drug cisplatin, a series of copper (II) complexes possessing alkyl-substituted polypyridyl ligands have been synthesized. Eight new complexes are reported herein: μ-dichloro-bis{2,9-di-sec-butyl-1,10-phenanthrolinechlorocopper(II)} {[(di-sec-butylphen)ClCu(μ-Cl)2CuCl(di-sec-butylphen)]}(1), 2-sec-butyl-1,10-phenanthrolinedichlorocopper(II) {[mono-sec-butylphen) CuCl2} (2), 2,9-di-n-butyl-1,10-phenanthrolinedichlorocopper(II) {[di-n-butylphen) CuCl2}(3), 2-n-butyl-1,10-phenanthrolinedichlorocopper(II) {[mono-n-butylphen) CuCl2} (4), 2,9-di-methyl-1,10-phenanthrolineaquadichlorocopper(II) {[di-methylphen) Cu(H2O)Cl2}(5), μ-dichloro-bis{6-sec-butyl-2,2′-bipyridinedichlorocopper(II)} {(mono-sec-butylbipy) ClCu(μ-Cl)2CuCl(mono-sec-butylbipy)} (6), 6,6′-di-methyl-2,2′-bipyridinedichlorocopper(II) {6,6′-di-methylbipy) CuCl2} (7), and 4,4′-dimethyl-2,2′-bipyridinedichlorocopper(II) {4,4′-di-methylbipy) CuCl2} (8). These complexes have been characterized via elemental analysis, UV–vis spectroscopy, and mass spectrometry. Single crystal X-ray diffraction experiments revealed the complexes synthesized with the di-sec-butylphen ligand (1) and mono-sec-butylbipy ligand (6) crystallized as dimers in which two copper(II) centers are bridged by two chloride ligands. Conversely, complexes 2, 7, and 8 were isolated as monomeric species possessing distorted tetrahedral geometries, and the [(di-methylphen)Cu(H2O)Cl2] (5) complex was isolated as a distorted square pyramidal monomer possessing a coordinating aqua ligand. Compounds 1–8 were evaluated for their in vitro antitumor efficacy. Compounds 1, 5, and 7 in particular were found to exhibit remarkable activity against human derived lung cancer cells, yet this class of copper(II) compounds had minimal cytotoxic effect on non-cancerous cells. In vitro control experiments indicate the activity of the copper(II) complexes most likely does not arise from the formation of CuCl2 and free polypyridyl ligand, and preliminary solution state studies suggest these compounds are generally stable in biological buffer. The results presented herein suggest further development of this class of copper-based drugs as potential anti-cancer therapies should be pursued.
Treatment of lung cancer cell line A549 with of alkyl-substituted polypyridyl copper(II) complexes shows promising antiproliferative activity as well as a high degree of selectivity for cancerous cells over benign somatic cells. [Display omitted]
•Eight new copper(II) coordination complexes synthesized and characterized•Copper(II) complexes possess alky-substituted 1,10-phenanthroline and 2,2′-bipyridine ligands.•Five copper(II) complexes characterized by single crystal X-ray diffraction•Three distorted tetrahedral, one distorted square pyramidal, and one dimeric complex described•Copper(II) complexes exhibit general in-vitro antitumor activity against lung tumor cells. |
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AbstractList | In an effort to find alternatives to the antitumor drug cisplatin, a series of copper (II) complexes possessing alkyl-substituted polypyridyl ligands have been synthesized. Eight new complexes are reported herein: μ-dichloro-bis{2,9-di-sec-butyl-1,10-phenanthrolinechlorocopper(II)} {[(di-sec-butylphen)ClCu(μ-Cl)2CuCl(di-sec-butylphen)]}(1), 2-sec-butyl-1,10-phenanthrolinedichlorocopper(II) {[mono-sec-butylphen) CuCl2} (2), 2,9-di-n-butyl-1,10-phenanthrolinedichlorocopper(II) {[di-n-butylphen) CuCl2}(3), 2-n-butyl-1,10-phenanthrolinedichlorocopper(II) {[mono-n-butylphen) CuCl2} (4), 2,9-di-methyl-1,10-phenanthrolineaquadichlorocopper(II) {[di-methylphen) Cu(H2O)Cl2}(5), μ-dichloro-bis{6-sec-butyl-2,2'-bipyridinedichlorocopper(II)} {(mono-sec-butylbipy) ClCu(μ-Cl)2CuCl(mono-sec-butylbipy)} (6), 6,6'-di-methyl-2,2'-bipyridinedichlorocopper(II) {6,6'-di-methylbipy) CuCl2} (7), and 4,4'-dimethyl-2,2'-bipyridinedichlorocopper(II) {4,4'-di-methylbipy) CuCl2} (8). These complexes have been characterized via elemental analysis, UV-vis spectroscopy, and mass spectrometry. Single crystal X-ray diffraction experiments revealed the complexes synthesized with the di-sec-butylphen ligand (1) and mono-sec-butylbipy ligand (6) crystallized as dimers in which two copper(II) centers are bridged by two chloride ligands. Conversely, complexes 2, 7, and 8 were isolated as monomeric species possessing distorted tetrahedral geometries, and the [(di-methylphen)Cu(H2O)Cl2] (5) complex was isolated as a distorted square pyramidal monomer possessing a coordinating aqua ligand. Compounds 1-8 were evaluated for their in vitro antitumor efficacy. Compounds 1, 5, and 7 in particular were found to exhibit remarkable activity against human derived lung cancer cells, yet this class of copper(II) compounds had minimal cytotoxic effect on non-cancerous cells. In vitro control experiments indicate the activity of the copper(II) complexes most likely does not arise from the formation of CuCl2 and free polypyridyl ligand, and preliminary solution state studies suggest these compounds are generally stable in biological buffer. The results presented herein suggest further development of this class of copper-based drugs as potential anti-cancer therapies should be pursued. In an effort to find alternatives to the antitumor drug cisplatin, a series of copper (II) complexes possessing alkyl-substituted polypyridyl ligands have been synthesized. Eight new complexes are reported herein: μ-dichloro-bis{2,9-di-sec-butyl-1,10-phenanthrolinechlorocopper(II)} {[( phen)ClCu(μ-Cl) CuCl( phen)]}(1), 2-sec-butyl-1,10-phenanthrolinedichlorocopper(II) { phen) CuCl } (2), 2,9-di-n-butyl-1,10-phenanthrolinedichlorocopper(II) {[ phen) CuCl }(3), 2-n-butyl-1,10-phenanthrolinedichlorocopper(II) {[ phen) CuCl } (4), 2,9-di-methyl-1,10-phenanthrolineaquadichlorocopper(II) {[ phen) Cu(H O)Cl }(5), μ-dichloro-bis{6-sec-butyl-2,2'-bipyridinedichlorocopper(II)} {( bipy) ClCu(μ-Cl) CuCl( bipy)} (6), 6,6'-di-methyl-2,2'-bipyridinedichlorocopper(II) { bipy) CuCl } (7), and 4,4'-dimethyl-2,2'-bipyridinedichlorocopper(II) { bipy) CuCl } (8). These complexes have been characterized via elemental analysis, UV-vis spectroscopy, and mass spectrometry. Single crystal X-ray diffraction experiments revealed the complexes synthesized with the phen ligand (1) and bipy ligand (6) crystallized as dimers in which two copper(II) centers are bridged by two chloride ligands. Conversely, complexes 2, 7, and 8 were isolated as monomeric species possessing distorted tetrahedral geometries, and the [( phen)Cu(H O)Cl ] (5) complex was isolated as a distorted square pyramidal monomer possessing a coordinating aqua ligand. Compounds 1-8 were evaluated for their in vitro antitumor efficacy. Compounds 1, 5, and 7 in particular were found to exhibit remarkable activity against human derived lung cancer cells, yet this class of copper(II) compounds had minimal cytotoxic effect on non-cancerous cells. In vitro control experiments indicate the activity of the copper(II) complexes most likely does not arise from the formation of CuCl and free polypyridyl ligand, and preliminary solution state studies suggest these compounds are generally stable in biological buffer. The results presented herein suggest further development of this class of copper-based drugs as potential anti-cancer therapies should be pursued. In an effort to find alternatives to the antitumor drug cisplatin, a series of copper (II) complexes possessing alkyl-substituted polypyridyl ligands have been synthesized. Eight new complexes are reported herein: μ-dichloro-bis{2,9-di-sec-butyl-1,10-phenanthrolinechlorocopper(II)} {[(di-sec-butylphen)ClCu(μ-Cl)2CuCl(di-sec-butylphen)]}(1), 2-sec-butyl-1,10-phenanthrolinedichlorocopper(II) {[mono-sec-butylphen) CuCl2} (2), 2,9-di-n-butyl-1,10-phenanthrolinedichlorocopper(II) {[di-n-butylphen) CuCl2}(3), 2-n-butyl-1,10-phenanthrolinedichlorocopper(II) {[mono-n-butylphen) CuCl2} (4), 2,9-di-methyl-1,10-phenanthrolineaquadichlorocopper(II) {[di-methylphen) Cu(H2O)Cl2}(5), μ-dichloro-bis{6-sec-butyl-2,2′-bipyridinedichlorocopper(II)} {(mono-sec-butylbipy) ClCu(μ-Cl)2CuCl(mono-sec-butylbipy)} (6), 6,6′-di-methyl-2,2′-bipyridinedichlorocopper(II) {6,6′-di-methylbipy) CuCl2} (7), and 4,4′-dimethyl-2,2′-bipyridinedichlorocopper(II) {4,4′-di-methylbipy) CuCl2} (8). These complexes have been characterized via elemental analysis, UV–vis spectroscopy, and mass spectrometry. Single crystal X-ray diffraction experiments revealed the complexes synthesized with the di-sec-butylphen ligand (1) and mono-sec-butylbipy ligand (6) crystallized as dimers in which two copper(II) centers are bridged by two chloride ligands. Conversely, complexes 2, 7, and 8 were isolated as monomeric species possessing distorted tetrahedral geometries, and the [(di-methylphen)Cu(H2O)Cl2] (5) complex was isolated as a distorted square pyramidal monomer possessing a coordinating aqua ligand. Compounds 1–8 were evaluated for their in vitro antitumor efficacy. Compounds 1, 5, and 7 in particular were found to exhibit remarkable activity against human derived lung cancer cells, yet this class of copper(II) compounds had minimal cytotoxic effect on non-cancerous cells. In vitro control experiments indicate the activity of the copper(II) complexes most likely does not arise from the formation of CuCl2 and free polypyridyl ligand, and preliminary solution state studies suggest these compounds are generally stable in biological buffer. The results presented herein suggest further development of this class of copper-based drugs as potential anti-cancer therapies should be pursued. Treatment of lung cancer cell line A549 with of alkyl-substituted polypyridyl copper(II) complexes shows promising antiproliferative activity as well as a high degree of selectivity for cancerous cells over benign somatic cells. [Display omitted] •Eight new copper(II) coordination complexes synthesized and characterized•Copper(II) complexes possess alky-substituted 1,10-phenanthroline and 2,2′-bipyridine ligands.•Five copper(II) complexes characterized by single crystal X-ray diffraction•Three distorted tetrahedral, one distorted square pyramidal, and one dimeric complex described•Copper(II) complexes exhibit general in-vitro antitumor activity against lung tumor cells. |
Author | Jenkins, Julia Le, Brian Khoa Angel, Noah R. Wilson, Emma H. Tham, Fook S. Lussier, Daniel Chen, Zhuo (Georgia) Eichler, Jack F. Rubalcava, Justin M. Smith, Michelle Khatib, Raneen M. |
Author_xml | – sequence: 1 givenname: Noah R. surname: Angel fullname: Angel, Noah R. organization: University of California, Riverside Department of Chemistry, 501 Big Springs Rd., Riverside, CA 92521, United States – sequence: 2 givenname: Raneen M. surname: Khatib fullname: Khatib, Raneen M. organization: University of California, Riverside Department of Chemistry, 501 Big Springs Rd., Riverside, CA 92521, United States – sequence: 3 givenname: Julia surname: Jenkins fullname: Jenkins, Julia organization: University of California, Riverside Department of Chemistry, 501 Big Springs Rd., Riverside, CA 92521, United States – sequence: 4 givenname: Michelle surname: Smith fullname: Smith, Michelle organization: University of California, Riverside Department of Chemistry, 501 Big Springs Rd., Riverside, CA 92521, United States – sequence: 5 givenname: Justin M. surname: Rubalcava fullname: Rubalcava, Justin M. organization: University of California, Riverside Department of Chemistry, 501 Big Springs Rd., Riverside, CA 92521, United States – sequence: 6 givenname: Brian Khoa surname: Le fullname: Le, Brian Khoa organization: University of California, Riverside Department of Chemistry, 501 Big Springs Rd., Riverside, CA 92521, United States – sequence: 7 givenname: Daniel surname: Lussier fullname: Lussier, Daniel organization: University of California, Riverside Department of Chemistry, 501 Big Springs Rd., Riverside, CA 92521, United States – sequence: 8 givenname: Zhuo (Georgia) surname: Chen fullname: Chen, Zhuo (Georgia) organization: Emory University Winship Cancer Institute, United States – sequence: 9 givenname: Fook S. surname: Tham fullname: Tham, Fook S. organization: University of California, Riverside Department of Chemistry, 501 Big Springs Rd., Riverside, CA 92521, United States – sequence: 10 givenname: Emma H. surname: Wilson fullname: Wilson, Emma H. organization: University of California, Riverside School of Medicine, Division of Biomedical Sciences, United States – sequence: 11 givenname: Jack F. surname: Eichler fullname: Eichler, Jack F. email: jack.eichler@ucr.edu organization: University of California, Riverside Department of Chemistry, 501 Big Springs Rd., Riverside, CA 92521, United States |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27815978$$D View this record in MEDLINE/PubMed |
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Keywords | Polypyridyl Synthesis Phenanthroline Anticancer Bipyrydine Copper(II) |
Language | English |
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Snippet | In an effort to find alternatives to the antitumor drug cisplatin, a series of copper (II) complexes possessing alkyl-substituted polypyridyl ligands have been... |
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SubjectTerms | A549 Cells Anticancer Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Bipyrydine Coordination Complexes - chemical synthesis Coordination Complexes - chemistry Coordination Complexes - pharmacology Copper - chemistry Copper - pharmacology Copper(II) Crystallography, X-Ray Drug Screening Assays, Antitumor Humans Molecular Structure Phenanthroline Polypyridyl Pyridines - chemistry Pyridines - pharmacology Synthesis |
Title | Copper (II) complexes possessing alkyl-substituted polypyridyl ligands: Structural characterization and in vitro antitumor activity |
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