Novel N-heterocyclic ylideneamine gold(i) complexes: synthesis, characterisation and screening for antitumour and antimalarial activity

Coetzee, Jacorien; Cronje, Stephanie; Dobrzańska, Liliana; Raubenheimer, Helgard G.; Jooné, G. K.; Nell, Margo; Hoppe, Heinrich C.

doi:10.1039/c0dt01312a

Cited by 30 publications

(26 citation statements)

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“…Analysis by 13 C{ 1 H} NMR spectroscopy revealed that the central isothiouronium carbon (N=C−N) was shifted downfield in all complexes, relative to the parent isothiourea (Δ δ C =+5–10 ppm). The magnitude of this downfield shift is consistent with those previously reported for gold(I)‐isothiourea complexes, and indicates that the positive charge is delocalized into the isothiourea ligand, and at least partially centralized on the isothiouronium carbon. The carbenic carbons of the NHC‐Au‐isothiourea complexes 9 , 10 , 17 , and 18 were observed at 171–172 ppm (Table , entries 2,3,6,7).…”

Section: Resultsmentioning

confidence: 99%

“…Schmidbaur and Cronje have reported the synthesis and characterization of neutral and cationic gold(I)‐guanidine and isothiourea complexes 3 and 4 (Figure ); however, these studies were mostly limited to the solution and solid‐state behaviour of the complexes. Cronje also applied these novel gold complexes in antitumoral and antimalarial screening, however only minimal activity was observed . Even more scarce are reports on the synthesis of gold complexes bearing chiral sp 2 ‐hybridized nitrogen‐based ligands.…”

Section: Introductionmentioning

confidence: 99%

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Chiral Au^I‐ and Au^III‐Isothiourea Complexes: Synthesis, Characterization and Application

Gasperini

Greenhalgh

Imad

et al. 2018

Chemistry A European J

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During an investigation into the potential union of Lewis basic isothiourea organocatalysis and gold catalysis, the formation of gold‐isothiourea complexes was observed. These novel gold complexes were formed in high yield and were found to be air‐ and moisture stable. A series of neutral and cationic chiral gold(I) and gold(III) complexes bearing enantiopure isothiourea ligands was therefore synthesized and fully characterized. The steric and electronic properties of the isothiourea ligands was assessed through calculation of their percent buried volume and the synthesis and analysis of novel iridium(I)‐isothiourea carbonyl complexes. The novel gold(I)‐ and gold(III)‐isothiourea complexes have been applied in preliminary catalytic and biological studies, and display promising preliminary levels of catalytic activity and potency towards cancerous cell lines and clinically relevant enzymes.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chiral Au^I‐ and Au^III‐Isothiourea Complexes: Synthesis, Characterization and Application

Gasperini

Greenhalgh

Imad

et al. 2018

Chemistry A European J

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“…Scheme 1 Gold(I) complexes of imidazolate (1)(2)(3)(4)(5), pyrazolate (5-9), 1,2,3-triazolate (10-14), 1,2,4-triazolate (15-18) and pyrrolate (19).…”

Section: List Of Figure Captionsmentioning

confidence: 99%

“…Exocyclic imine complexation of azol-2-ylideneamine ligands with [(Ph 3 P)Au] + increases their antitumour as well as antimalarial activity [19].…”

Section: Introductionmentioning

confidence: 99%

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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“…In addition, the biological and analgesic activities of many heterocyclic compounds containing a sulfur atom have been reviewed (Lorrain et al, 2003). On the other hand, some of the nitrogenous candidates have promising biological (Coetzee et al, 2011) and anticancer activities (Amr et al, 2006a, b). Recently, some new Schiff base derivatives have been synthesized Al-Salahi et al, 2010) and tested as antimicrobial agents.…”

Section: Introductionmentioning

confidence: 99%

Analgesic and Anticonvulsant Activities of Some Newly Synthesized Trisubstituted Pyridine Derivatives

Salam

Al‐Omar

Khalifa

et al. 2013

Zeitschrift Für Naturforschung C

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A series of novel pyridine carbohydrazide derivatives were synthesized from the reaction of 2-chloro-6-hydrazino-isonicotinic acid hydrazide with selected active reagents. All prepared compounds were tested as analgesic and anticonvulsant agents. The pharmacological screening showed that many of these compounds have good activities comparable to those of valdecoxib and carbamazepine as reference drugs.

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Novel N-heterocyclic ylideneamine gold(i) complexes: synthesis, characterisation and screening for antitumour and antimalarial activity

Cited by 30 publications

References 44 publications

Chiral Au^I‐ and Au^III‐Isothiourea Complexes: Synthesis, Characterization and Application

Chiral Au^I‐ and Au^III‐Isothiourea Complexes: Synthesis, Characterization and Application

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

Analgesic and Anticonvulsant Activities of Some Newly Synthesized Trisubstituted Pyridine Derivatives

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Novel N-heterocyclic ylideneamine gold(i) complexes: synthesis, characterisation and screening for antitumour and antimalarial activity

Cited by 30 publications

References 44 publications

Chiral AuI‐ and AuIII‐Isothiourea Complexes: Synthesis, Characterization and Application

Chiral AuI‐ and AuIII‐Isothiourea Complexes: Synthesis, Characterization and Application

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

Analgesic and Anticonvulsant Activities of Some Newly Synthesized Trisubstituted Pyridine Derivatives

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Chiral Au^I‐ and Au^III‐Isothiourea Complexes: Synthesis, Characterization and Application

Chiral Au^I‐ and Au^III‐Isothiourea Complexes: Synthesis, Characterization and Application