dc.contributor.author |
Van der Westhuizen, D
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|
dc.contributor.author |
Slabber, CA
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|
dc.contributor.author |
Fernandes, MA
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dc.contributor.author |
Joubert, DF
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dc.contributor.author |
Kleinhans, G
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dc.contributor.author |
Van der Westhuizen, Carl J
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dc.contributor.author |
Stander, A
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dc.contributor.author |
Munro, OQ
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dc.contributor.author |
Bezuidenhout, DI
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dc.date.accessioned |
2022-03-13T16:49:27Z |
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dc.date.available |
2022-03-13T16:49:27Z |
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dc.date.issued |
2021-06 |
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dc.identifier.citation |
Van der Westhuizen, D., Slabber, C., Fernandes, M., Joubert, D., Kleinhans, G., Van der Westhuizen, C.J., Stander, A. & Munro, O. et al. 2021. A Cytotoxic Bis(1,2,3-triazol-5-ylidene)carbazolide Gold(III) complex targets DNA by partial intercalation. <i>Chemistry—A European Journal, 27(32).</i> http://hdl.handle.net/10204/12316 |
en_ZA |
dc.identifier.issn |
0947-6539 |
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dc.identifier.issn |
1521-3765 |
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dc.identifier.uri |
https://doi.org/10.1002/chem.202100598
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dc.identifier.uri |
http://hdl.handle.net/10204/12316
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|
dc.description.abstract |
The syntheses of bis(triazolium)carbazole precursors and their corresponding coinage metal (Au, Ag) complexes are reported. For alkylated triazolium salts, di- or tetranuclear complexes with bridging ligands were isolated, while the bis(aryl) analogue afforded a bis(carbene) AuI-CNC pincer complex suitable for oxidation to the redox-stable [AuIII(CNC)Cl]+ cation. Although the ligand salt and the [AuIII(CNC)Cl]+ complex were both notably cytotoxic toward the breast cancer cell line MDA-MB-231, the AuIII complex was somewhat more selective. Electrophoresis, viscometry, UV-vis, CD and LD spectroscopy suggest the cytotoxic [AuIII(CNC)Cl]+ complex behaves as a partial DNA intercalator. In silico screening indicated that the [AuIII(CNC)Cl]+ complex can target DNA three-way junctions with good specificity, several other regular B-DNA forms, and Z-DNA. Multiple hydrophobic p-type interactions involving T and A bases appear to be important for B-form DNA binding, while phosphate O... interactions evidently underpin Z-DNA binding. The CNC ligand effectively stabilizes the AuIII ion, preventing reduction in the presence of glutathione. Both the redox stability and DNA affinity of the hit compound might be key factors underpinning its cytotoxicity in vitro. |
en_US |
dc.format |
Fulltext |
en_US |
dc.language.iso |
en |
en_US |
dc.relation.uri |
https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202100598 |
en_US |
dc.source |
Chemistry—A European Journal, 27(32) |
en_US |
dc.subject |
Chemistry |
en_US |
dc.subject |
Bis(triazolium)carbazole precursors |
en_US |
dc.subject |
Alkylated triazolium salts |
en_US |
dc.title |
A Cytotoxic Bis(1,2,3-triazol-5-ylidene)carbazolide Gold(III) complex targets DNA by partial intercalation |
en_US |
dc.type |
Article |
en_US |
dc.description.pages |
8295-8307 |
en_US |
dc.description.note |
Copyright: 2021 The Authors |
en_US |
dc.description.cluster |
Chemicals |
en_US |
dc.description.impactarea |
Pharmaceutical Technologies |
en_US |
dc.identifier.apacitation |
Van der Westhuizen, D., Slabber, C., Fernandes, M., Joubert, D., Kleinhans, G., Van der Westhuizen, C. J., ... Bezuidenhout, D. (2021). A Cytotoxic Bis(1,2,3-triazol-5-ylidene)carbazolide Gold(III) complex targets DNA by partial intercalation. <i>Chemistry—A European Journal, 27(32)</i>, http://hdl.handle.net/10204/12316 |
en_ZA |
dc.identifier.chicagocitation |
Van der Westhuizen, D, CA Slabber, MA Fernandes, DF Joubert, G Kleinhans, Carl J Van der Westhuizen, A Stander, OQ Munro, and DI Bezuidenhout "A Cytotoxic Bis(1,2,3-triazol-5-ylidene)carbazolide Gold(III) complex targets DNA by partial intercalation." <i>Chemistry—A European Journal, 27(32)</i> (2021) http://hdl.handle.net/10204/12316 |
en_ZA |
dc.identifier.vancouvercitation |
Van der Westhuizen D, Slabber C, Fernandes M, Joubert D, Kleinhans G, Van der Westhuizen CJ, et al. A Cytotoxic Bis(1,2,3-triazol-5-ylidene)carbazolide Gold(III) complex targets DNA by partial intercalation. Chemistry—A European Journal, 27(32). 2021; http://hdl.handle.net/10204/12316. |
en_ZA |
dc.identifier.ris |
TY - Article
AU - Van der Westhuizen, D
AU - Slabber, CA
AU - Fernandes, MA
AU - Joubert, DF
AU - Kleinhans, G
AU - Van der Westhuizen, Carl J
AU - Stander, A
AU - Munro, OQ
AU - Bezuidenhout, DI
AB - © 2021 The Authors.
DA - 2021-06
DB - ResearchSpace
DP - CSIR
J1 - Chemistry—A European Journal, 27(32)
KW - Chemistry
KW - Bis(triazolium)carbazole precursors
KW - Alkylated triazolium salts
LK - https://researchspace.csir.co.za
PY - 2021
SM - 0947-6539
SM - 1521-3765
T1 - A Cytotoxic Bis(1,2,3-triazol-5-ylidene)carbazolide Gold(III) complex targets DNA by partial intercalation
TI - A Cytotoxic Bis(1,2,3-triazol-5-ylidene)carbazolide Gold(III) complex targets DNA by partial intercalation
UR - http://hdl.handle.net/10204/12316
ER -
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en_ZA |
dc.identifier.worklist |
25443 |
en_US |