Synthesis and cytotoxic characteristics displayed by a series of Ag(<scp>i</scp>)-, Au(<scp>i</scp>)- and Au(<scp>iii</scp>)-complexes supported by a common N-heterocyclic carbene

Jhulki, Lalmohan; Dutta, Parul; Santra, Manas Kumar; Cardoso, Marlon Henrique; Oshiro, Karen G. N.; Franco, Octávio Luiz; Bertolasi, Valerio; Isab, Anvarhusein A.; Bielawski, Christopher W.; Dinda, Joydev

doi:10.1039/c8nj02008f

Cited by 25 publications

(12 citation statements)

References 68 publications

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“…Other groups were evaluated in vitro for the cytotoxicities of Au and Ag NHCs complexes supported by a pyridine, annulated imidazole-2-ylidene ( 21 ) [ 117 , 118 ], imidazolium salt 1-naphthyl-2-pyridin-2-yl-2H-imidazo[1,5-a]pyridin-4-ylium hexafluorophosphate ( 22 ) [ 119 ], pyridyl[1,2-a]{2-acetylylphenylimidazol}-3-ylidene ( 23 ) [ 120 ] ( Figure 9 ). All complexes of Au(III)–NHC exhibited lower cytotoxicity than Ag(I) and Au(I) complexes for nearly all cell lines tested.…”

Section: In Vitro Studiesmentioning

confidence: 99%

Gold (III) Derivatives in Colon Cancer Treatment

Gurba

Taciak

Sacharczuk

et al. 2022

IJMS

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Cancer is one of the leading causes of morbidity and mortality worldwide. Colorectal cancer (CRC) is the third most frequently diagnosed cancer in men and the second in women. Standard patterns of antitumor therapy, including cisplatin, are ineffective due to their lack of specificity for tumor cells, development of drug resistance, and severe side effects. For this reason, new methods and strategies for CRC treatment are urgently needed. Current research includes novel platinum (Pt)- and other metal-based drugs such as gold (Au), silver (Ag), iridium (Ir), or ruthenium (Ru). Au(III) compounds are promising drug candidates for CRC treatment due to their structural similarity to Pt(II). Their advantage is their relatively good solubility in water, but their disadvantage is an unsatisfactory stability under physiological conditions. Due to these limitations, work is still underway to improve the formula of Au(III) complexes by combining with various types of ligands capable of stabilizing the Au(III) cation and preventing its reduction under physiological conditions. This review summarizes the achievements in the field of stable Au(III) complexes with potential cytotoxic activity restricted to cancer cells. Moreover, it has been shown that not nucleic acids but various protein structures such as thioredoxin reductase (TrxR) mediate the antitumor effects of Au derivatives. The state of the art of the in vivo studies so far conducted is also described.

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Section: In Vitro Studiesmentioning

confidence: 99%

Gold (III) Derivatives in Colon Cancer Treatment

Gurba

Taciak

Sacharczuk

et al. 2022

IJMS

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“…Compound 282 displayed potent activity against the tested cell line with IC 50 value in the range of 0.8–5.75 μM compared to complex 283 (IC 50 value in the range of 10–24 μM) (Table 8). Au III −NHC complex 283 displayed less activity compared to 282 due to the reduction of Au III to Au I upon contact with intracellular thiols [163] . Niu et al.…”

Section: Medicinal Applicationsmentioning

confidence: 99%

“…Au III À NHC complex 283 displayed less activity compared to 282 due to the reduction of Au III to Au I upon contact with intracellular thiols. [163] Niu et al developed new gold(I)À NHC complexes 284 and 285 (Figure 17), which were tested against four cancer cell lines (CCRF-CEM, MDA-MB-231, DU145, HeLa) and two normal cell lines (HEK293, HU1545v). The cationic complex 285 exhibited higher cytotoxicity (IC 50 value 4.2-32.7 μM) towards tested cell lines compared to complex 284.…”

Section: Auà Nhc Complexes As Anticancer Agentsmentioning

confidence: 99%

Coinage Metal N‐Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications

Nayak

Gaonkar

2021

ChemMedChem

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New weapons are constantly needed in the fight against cancer. The discovery of cisplatin as an anticancer drug prompted the search for new metal complexes. The successful history of cisplatin motivated chemists to develop a plethora of metal‐based molecules. Among them, metal‐N‐heterocyclic carbene (NHC) complexes have gained significant attention because of their suitable qualities for efficient drug design. The enhanced applications of coinage metal‐NHC complexes have encouraged a gradually increasing number of studies in the fields of medicinal chemistry that benefit from the fascinating chemical properties of these complexes. This review aims to present recent developments in synthetic strategies and medicinal applications of copper, silver and gold complexes supported by NHC ligands.

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“…Gold(I) carbene compounds derived from pyridine annulated imidazole-2-ylidene, namely 1-methyl-2-(phenyl)imidazo[1,5-a]pyridine-2-ylidene and 2-pyridin-2-yl-2H-imidazo[1,5-a]pyridin-4-ylidene, were described, explored for their effect on human colorectal adenocarcinoma HCT-116, and compared with the corresponding gold(III) homologous complexes. In general, gold(I) complexes 94a–b displayed a higher cytotoxicity (IC 50 values of 2.25 and 0.82 µM, respectively) than the Au(III) analogues 95a–b (IC 50 values of 4.73 and 21.25 µM, respectively); however, higher IC 50 values have been described for the methyl counterpart 95a in comparison with 95b [110,111]. All complexes inhibited cell growth through the induction of apoptosis.…”

Section: Gold(i) Complexesmentioning

confidence: 99%

“…All complexes inhibited cell growth through the induction of apoptosis. Additional molecular docking studies on complexes 94b and 95b with B-cell CLL/lymphoma 2 (BCL-2) and human topoisomerase I (Topol I) coupled with a DNA strand afforded complex 94b, which exhibited the highest affinity with BCL-2 and different binding affinities in both 94b and 95b complexes towards a DNA strand in a topoisomerase/DNA complex, which may interrupt the ability of the enzyme to hydrolyze the DNA phosphodiester bonds [110].…”

Section: Gold(i) Complexesmentioning

confidence: 99%

Gold as a Possible Alternative to Platinum-Based Chemotherapy for Colon Cancer Treatment

Mármol

Medina-Quero

Rodríguez-Yoldi

et al. 2019

Cancers

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Due to the increasing incidence and high mortality associated with colorectal cancer (CRC), novel therapeutic strategies are urgently needed. Classic chemotherapy against CRC is based on oxaliplatin and other cisplatin analogues; however, platinum-based therapy lacks selectivity to cancer cells and leads to deleterious side effects. In addition, tumor resistance to oxaliplatin is related to chemotherapy failure. Gold(I) derivatives are a promising alternative to platinum complexes, since instead of interacting with DNA, they target proteins overexpressed on tumor cells, thus leading to less side effects than, but a comparable antitumor effect to, platinum derivatives. Moreover, given the huge potential of gold nanoparticles, the role of gold in CRC chemotherapy is not limited to gold(I) complexes. Gold nanoparticles have been found to be able to overcome multidrug resistance along with reduced side effects due to a more efficient uptake of classic drugs. Moreover, the use of gold nanoparticles has enhanced the effect of traditional therapies such as radiotherapy, photothermal therapy, or photodynamic therapy, and has displayed a potential role in diagnosis as a consequence of their optic properties. Herein, we have reviewed the most recent advances in the use of gold(I) derivatives and gold nanoparticles in CRC therapy.

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Synthesis and cytotoxic characteristics displayed by a series of Ag(i)-, Au(i)- and Au(iii)-complexes supported by a common N-heterocyclic carbene

Abstract: The design, synthesis and anticancer properties of a series of Ag(i), Au(i) and Au(iii)–NHC complexes supported by pyridyl[1,2-a]{2-acetylylphenylimidazol}-3-ylidene are described.

Cited by 25 publications

References 68 publications

Gold (III) Derivatives in Colon Cancer Treatment

Gold (III) Derivatives in Colon Cancer Treatment

Coinage Metal N‐Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications

Gold as a Possible Alternative to Platinum-Based Chemotherapy for Colon Cancer Treatment

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