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Synthesis, characterization and biological activity of bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes.
Dalton Trans. 2020 May 07; 49(17):5471-5481.DT

Abstract

Bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes (8a-h) with methoxy, methyl and fluorine substituents at different positions of the 4-aryl ring were synthesized and characterized. The relevance of the 2-methoxypyridin-5-yl residue and the substituents at the 4-aryl ring with regard to the activity against a series of cell lines was determined. Particularly against the Cisplatin-resistant ovarian cancer cell line A2780cis, the most active bromido[3-ethyl-4-(4-methoxyphenyl)-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complex 8c was more active than Auranofin. It also inhibited thioredoxin reductase more effectively and induced high amounts of reactive oxygen species in A2780cis cells. Furthermore, its influence on non-cancerous SV 80 lung fibroblasts was lower than that of Auranofin. This fact, together with a high accumulation rate in tumor cells, determined on the example of MCF-7 cells, makes this complex an interesting candidate for further extensive studies.

Authors+Show Affiliations

Department of Pharmaceutical Chemistry, Institute of Pharmacy, Center for Molecular Biosciences Innsbruck, University of Innsbruck, Innrain 80/82, A-6020 Innsbruck, Austria. ronald.gust@uibk.ac.at.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32255443

Citation

Gallati, Caroline M., et al. "Synthesis, Characterization and Biological Activity of bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) Complexes." Dalton Transactions (Cambridge, England : 2003), vol. 49, no. 17, 2020, pp. 5471-5481.
Gallati CM, Goetzfried SK, Ausserer M, et al. Synthesis, characterization and biological activity of bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes. Dalton Trans. 2020;49(17):5471-5481.
Gallati, C. M., Goetzfried, S. K., Ausserer, M., Sagasser, J., Plangger, M., Wurst, K., Hermann, M., Baecker, D., Kircher, B., & Gust, R. (2020). Synthesis, characterization and biological activity of bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes. Dalton Transactions (Cambridge, England : 2003), 49(17), 5471-5481. https://doi.org/10.1039/c9dt04824c
Gallati CM, et al. Synthesis, Characterization and Biological Activity of bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) Complexes. Dalton Trans. 2020 May 7;49(17):5471-5481. PubMed PMID: 32255443.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis, characterization and biological activity of bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes. AU - Gallati,Caroline M, AU - Goetzfried,Sina K, AU - Ausserer,Marjana, AU - Sagasser,Jessica, AU - Plangger,Matthias, AU - Wurst,Klaus, AU - Hermann,Martin, AU - Baecker,Daniel, AU - Kircher,Brigitte, AU - Gust,Ronald, Y1 - 2020/04/07/ PY - 2020/4/8/pubmed PY - 2020/4/8/medline PY - 2020/4/8/entrez SP - 5471 EP - 5481 JF - Dalton transactions (Cambridge, England : 2003) JO - Dalton Trans VL - 49 IS - 17 N2 - Bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes (8a-h) with methoxy, methyl and fluorine substituents at different positions of the 4-aryl ring were synthesized and characterized. The relevance of the 2-methoxypyridin-5-yl residue and the substituents at the 4-aryl ring with regard to the activity against a series of cell lines was determined. Particularly against the Cisplatin-resistant ovarian cancer cell line A2780cis, the most active bromido[3-ethyl-4-(4-methoxyphenyl)-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complex 8c was more active than Auranofin. It also inhibited thioredoxin reductase more effectively and induced high amounts of reactive oxygen species in A2780cis cells. Furthermore, its influence on non-cancerous SV 80 lung fibroblasts was lower than that of Auranofin. This fact, together with a high accumulation rate in tumor cells, determined on the example of MCF-7 cells, makes this complex an interesting candidate for further extensive studies. SN - 1477-9234 UR - https://www.unboundmedicine.com/medline/citation/32255443/Synthesis,_characterization_and_biological_activity_of_bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i)_complexes L2 - https://doi.org/10.1039/c9dt04824c DB - PRIME DP - Unbound Medicine ER -
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