Synthesis of gold(I), silver(I) and copper(I) complexes containing substituted (2-aminophenyl)phosphines. Molecular structures of [AuI(2-H2NC6H4PPh2)], [AuI{(±)-2-H2NC6H4PMePh}] and (±)-[Cu(2-H2NC6H4PPh2)2];PF6

Papathanasiou, Peter; Salem, Geoffrey; Waring, Paul; Willis, Anthony C.

doi:10.1039/a702757e

Cited by 48 publications

(23 citation statements)

References 18 publications

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“…106 Gold phosphine compounds containing a variable number of coordinated phosphorus atoms (from 1 to 4) show increased cytotoxic potency in murine tumor cell lines as the number of gold-coordinated phosphorus atoms increases. 107,108 Unfortunately, after relatively encouraging studies on selected tumor cell lines, [109][110][111][112] auranofin analogues containing thiolate ligands derived from thionucleobases (phosphine gold(I) thionucleobase compounds) have not demonstrated marked cytotoxic activity when screened through the National Cancer Institute's panel of 60 tumor cell lines. 113 However, related phosphine gold(I) thiolates show higher cytotoxic activity compared with cisplatin and 5-fluorouracil in seven human solid tumor cell lines.…”

Section: Preclinical Studies a In Vitro Studiesmentioning

confidence: 99%

Gold compounds as anticancer agents: chemistry, cellular pharmacology, and preclinical studies

et al. 2009

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Gold compounds are a class of metallodrugs with great potential for cancer treatment. During the last two decades, a large variety of gold(I) and gold(III) compounds are reported to possess relevant antiproliferative properties in vitro against selected human tumor cell lines, qualifying themselves as excellent candidates for further pharmacological evaluation. The unique chemical properties of the gold center confer very interesting and innovative pharmacological profiles to gold-based metallodrugs. The primary goal of this review is to define the state of the art of preclinical studies on anticancer gold compounds, carried out either in vitro or in vivo. The available investigations of anticancer gold compounds are analyzed in detail, and particular attention is devoted to underlying molecular mechanisms. Notably, a few biophysical studies reveal that the interactions of cytotoxic gold compounds with DNA are generally far weaker than those of platinum drugs, implying the occurrence of a substantially different mode of action. A variety of alternative mechanisms were thus proposed, of which those involving either direct mitochondrial damage or proteasome inhibition or modulation of specific kinases are now highly credited. The overall perspectives on the development of gold compounds as effective anticancer drugs with an innovative mechanism of action are critically discussed on the basis of the available experimental evidence.

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Section: Preclinical Studies a In Vitro Studiesmentioning

confidence: 99%

Gold compounds as anticancer agents: chemistry, cellular pharmacology, and preclinical studies

et al. 2009

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“…For instance, the compound [AuIL] (L ¼ (2-aminophenyl)methylphenylphosphine), which crystallizes as a racemic mixture of dimers [14], represents one example of a biologically active species. In the analogous species [AuIL] (L ¼ (2-aminophenyl)diphenylphosphine) gold-gold interactions are absent.…”

Section: Dinuclear Aggregatesmentioning

confidence: 99%

“…A chain structure is obtained by using the diphosphine p-bis(diphenylphosphino)benzene (Figure 2.29b). The complicated crystal structures of [Au 6 (m-Se) 2 (dppbp) 3 ]Cl 2 (dppbp ¼ 4,4 0 -bis(diphenylphosphino)biphenyl), [Au 34 (m-Se) 14 (tpep) 6 (tpep Se ) 2 ]Cl 6 (tpep ¼ 1,1,1,-tris(diphenyphosphinoethyl)phosphine; tpep Se ¼ 1,1,-bis(diphenyphosphinoethyl)-1-(diphenylselenophosphinoethyphosphine) have also been reported [137].…”

Section: Clustering Of Gold Atoms At One Centermentioning

confidence: 99%

Gold–Gold Interactions

Crespo

2008

Modern Supramolecular Gold Chemistry

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This chapter focuses mainly on closed shell gold(I) atoms which are found to feel attraction among themselves. This attraction is able to modify expected geometries or support one-, two-or three-dimensional arrays and also leads to interesting properties. Closed shell metal cations are expected to repel each other. Nevertheless, an important number of examples containing [d 8 -d 10 -s 2 ] interactions are known. Particularly strong evidence has been accumulated on the attraction between two or more d 10 shells. In the case of gold(I) such attraction between two or more monovalent gold(I) ions in compounds has been observed structurally for a long time. In these situations the gold centers approach each other to a distance of between 2.7 and 3.3 Å. This range includes the distance between gold atoms in gold metal and approaches, or even overlaps with the range of distances found in the few real Au-Au single bonds. Schmidbaur coined the name aurophilic attraction in 1990 and defined it as the unprecedented affinity between gold atoms even with closed-shell electronic configurations and equivalent electrical charges [1]. Since that moment, aurophilicity has become one of the hot topics in gold chemistry, at first with the aim of understanding such interaction, more recently because of the observation that it may play an important role in interesting properties, thus understanding and modulating aurophilic interactions could help to govern these properties, which include the optical behavior. Although different origins are possible for the luminescent emissions of coordination complexes, such as intraligand transitions (ILT), ligand to metal or metal to ligand charge transfer transitions (LMCT, MLCT) and metal centered (MCT) transitions, in many luminescent gold complexes the emissions have been related to the presence of aurophilic interactions.Information about aurophilicity and chemical situations in which it is observed may be found in different works that may be classified as those which analyse closed shell interactions in general [2], those focused on aurophilicity [1,3], and others which analyze the role of these interactions in coordination [4] and organometallic gold Modern Supramolecular Gold Chemistry: Gold-Metal Interactions and Applications. Edited by Antonio Laguna

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“…However, many gold(I) complexes have shown high toxicity and lack of selectivity for cancer cells (Hoke et al 1988(Hoke et al , 1989. Various silver(I) complexes have therefore been evaluated and have shown promising antitumor activity Papathanasiou et al 1997;McKeage et al 1998;Liu et al 2008;Zartilas et al 2009) suggesting the potential application of phosphine silver thiocyanate complexes as apoptosis inducing agents.…”

Section: Introductionmentioning

confidence: 97%

The effect of 1:2 Ag(I) thiocyanate complexes in MCF-7 breast cancer cells

et al. 2015

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There is much interest currently in the design of metal compounds as drugs and various metal compounds are already in clinical use. These include gold(I) compounds such as auranofin and the anti-cancer platinum(II) complex, cisplatin. Bis-chelated gold(I) phosphine complexes have also shown great potential as anticancer agents, however, their efficacy has been limited by their high toxicity. In this study, silver(I) thiocyanate compounds linked to four specific ligands, were synthesized and characterized. These silver-phosphine adducts included [AgSCN{P(4-MeC6H4)3}2]2 (1); [AgSCN{P(4-ClC6H4)3}2]2 (2); [AgSCN{P(4-MeOC6H4)3}2]2 (3); [AgSCN(PPh3)2]2 (4). The compounds were found to be toxic to MCF-7 breast cancer cells while the ligands on their own were not toxic. Our findings further indicate that the silver(I) phosphine compounds induce apoptotic cell death in these breast cancer cells. In addition, the compounds were not toxic to nonmalignant fibroblast cells at the IC50 concentrations. This is an indication that the compounds show selectivity towards the cancer cells.

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Synthesis of gold(I), silver(I) and copper(I) complexes containing substituted (2-aminophenyl)phosphines. Molecular structures of [AuI(2-H2NC6H4PPh2)], [AuI{(±)-2-H2NC6H4PMePh}] and (±)-[Cu(2-H2NC6H4PPh2)2];PF6

Cited by 48 publications

References 18 publications

Gold compounds as anticancer agents: chemistry, cellular pharmacology, and preclinical studies

Gold compounds as anticancer agents: chemistry, cellular pharmacology, and preclinical studies

Gold–Gold Interactions

The effect of 1:2 Ag(I) thiocyanate complexes in MCF-7 breast cancer cells

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