In vivo and in vitro cardiotoxicity of a gold-containing antineoplastic drug candidate in the rabbit

Hoke, Glenn D.; Macia, Richard A.; Meunier, Paul C.; Bugelski, Peter J.; Mirabelli, Christopher K.; Rush, Glenn F.; Matthews, William D.

doi:10.1016/0041-008x(89)90315-3

Cited by 71 publications

(50 citation statements)

References 17 publications

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“…13 38.35; H, 3.03; N, 3.06, found: C, 38.32; H, 3.25; N, 3.45 %. Tables Vol C Tables 4 .2.6.8 and 6.1.1.4' (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2001;Atwood & Barbour, 2003)' _computing_publication_material X-Seed _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^.…”

Section: Si 4123 Preparation Of Bis(1h-imidazolato-n 1 )(Trimethylmentioning

confidence: 99%

“…(4 H, s, H4, H5), 7.69 (8 H, m, m-C 6 H 5 ), 7.53 (12 H, m, p-and o-C 6 H 5 ), 2.80 (4 H, m, P-(CH 2 ) 2 -P). 13 C, 38.81; H, 3.04; N, 9.05, found: C, 38.92; H, 2.91; N, 9.45 %.…”

Section: Si 4111 Preparation Of {-[12-ethanediylbis(dimethylphospmentioning

confidence: 99%

“…Lipophilic cations, [(dppe) 2 Au]Cl, are a relatively new class of anticancer drugs displaying selective targeting of mitochondria with hyperpolarised membranes in cancer cells [14]. Strong anticancer activity has been detected for such compounds; however, in vivo toxicity remains too high for their clinical use [7,13]. In these cationic gold(I) disphosphines a decrease in lipophilicity correlates with enhanced selectivity while an increase in potency has been reported with increased lipophilicity [14].…”

Section: Introductionmentioning

confidence: 99%

“…Mitochondria are the primary target of both neutral, linear gold(I) phosphine compounds [11,13] as well as tetrahedral gold(I) phosphine cations [10,12]. The non-selectivity of cancer drugs in differentiating between tumour cells and normal tissue leads to severe host toxicity.…”

Section: Introductionmentioning

confidence: 99%

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Amides of gold(I) diphosphines prepared from N-heterocyclic sources and their in vitro and in vivo screening for anticancer activity

Horvath

Dobrzańska

Strasser

et al. 2012

Journal of Inorganic Biochemistry

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Synopsis __________________________________________________________________________Among a new series of gold(I) complexes that contain diphosphine and deprotonated N-heterocyclic ring systems as ligands, the compounds containing diphenyl(phosphino)pentane and pyrazolate (lypophilic) or 1,2,4,-triazolate (hydrophilic) have high anti-tumour specificities. They induce an apoptic cell death pathway and have the maximum tolerated dose of 1.5 μmol/kg when administered to Balb/C mice. ___________________________________________________________________ *Synopsis for the Graphical abstract  In 25 new complexes diphosphines and azolate-type ligands coordinate to gold  Solvent molecules and counterions appear within channels of a crystalline complex  Cytotoxicity is dependent upon aliphatic C chain length in the ligands  An apoptosis cell death with certain mitochondrial involvement is indicated  Tolerated doses compared to [Au(dppe) 2 ]Cl, tumour specificity is much better *Highlights A B S T R A C T ------------------------------------------------------------------------A series of new neutral mononuclear or dinuclear gold(I) complexes and a cyclic cationic tetranuclear amidogold(I) complex comprising of the phosphines 1,2-bis(dimethylphosphino)ethane (dmpe), μ-1,2-bis(diphenylphosphino)ethane (dppe), μ-1,3-bis(diphenylphosphino)propane (dppp), μ-1,5-bis(diphenylphosphino)pentane (dpppe), μ-1,6-bis(diphenylphosphino)hexane (dpph) or trimethylphosphine, and several N-heterocyclic ring systems (imidazolate, pyrazolate, 1,2,3-triazolate, 1,2,4-triazolate, pyrrolate, 9H-purine-9-ate or 9H-purine-6-amine-9-ate) as ligands, reveal intermolecular aurophilic interactions and 2D channels available for solvent molecules in some of their crystal structures. The antitumou r 2 activity of the acyclic gold(I) compounds is highly dependent on the substituents on the phosphorus atoms being highest for phenyl groups and lower for methyl groups. The activity of these compounds against selected cell lines is linked to the length of the carbon bridge between the two phosphorus atoms being highest with a bridge consisting of 5 or 6 carbons. Two compounds with the highest tumour specifities that contain dpppe and pyrazolate (a lipophilic compound) or 1,2,4-triazolate (a hydrophilic compound) induce the apoptic cell death pathway and tolerate a maximum dose of 1.5 μmol/kg when administered to Balb/C mice.

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Section: Si 4123 Preparation Of Bis(1h-imidazolato-n 1 )(Trimethylmentioning

confidence: 99%

“…(4 H, s, H4, H5), 7.69 (8 H, m, m-C 6 H 5 ), 7.53 (12 H, m, p-and o-C 6 H 5 ), 2.80 (4 H, m, P-(CH 2 ) 2 -P). 13 C, 38.81; H, 3.04; N, 9.05, found: C, 38.92; H, 2.91; N, 9.45 %.…”

Section: Si 4111 Preparation Of {-[12-ethanediylbis(dimethylphospmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Amides of gold(I) diphosphines prepared from N-heterocyclic sources and their in vitro and in vivo screening for anticancer activity

Horvath

Dobrzańska

Strasser

et al. 2012

Journal of Inorganic Biochemistry

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“…Gold may also increase apoptosis by opening the mitochondrial transition pore, resulting in mitochondrial swelling and depolarization (3). A goldcontaining, experimental antineoplastic drug, bis(1,2-bis(diphenylphosphino)ethane gold[I] chloride, causes myocardial contraction band necrosis, associated with a loss of mitochondrial function (4). BAL ( Figure 1B) is a disulphide that was synthesized in 1940 as an antidote to the arsenic-containing chemical warfare gas Lewisite (5).…”

Section: Literature Reviewmentioning

confidence: 99%

Dilated cardiomyopathy and left bundle branch block associated with ingestion of colloidal gold and silver is reversed by British antiLewisite and vitamin E: The potential toxicity of metals used as health supplements

Archer

2008

Canadian Journal of Cardiology

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Medicinal Chemistry of Gold Compounds

Fricker¹

2009

Patai's Chemistry of Functional Groups

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Metals in Biology Historical Use of Gold in Medicine Gold Therapy for Rheumatoid Arthritis Mechanism of Action of Antiarthritic Gold Drugs Antitumour Anti‐Infective Conclusion Acknowledgement

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In vivo and in vitro cardiotoxicity of a gold-containing antineoplastic drug candidate in the rabbit

Cited by 71 publications

References 17 publications

Amides of gold(I) diphosphines prepared from N-heterocyclic sources and their in vitro and in vivo screening for anticancer activity

Amides of gold(I) diphosphines prepared from N-heterocyclic sources and their in vitro and in vivo screening for anticancer activity

Dilated cardiomyopathy and left bundle branch block associated with ingestion of colloidal gold and silver is reversed by British antiLewisite and vitamin E: The potential toxicity of metals used as health supplements

Medicinal Chemistry of Gold Compounds

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