Tethered N-Heterocyclic Carbene-Carboranyl Silver Complexes for Cancer Therapy

Jordan Holmes, Rachel J. Kearsey, Katie A. Paske, Frances N. Singer, Suliman Atallah, Christopher M. Pask, Roger M. Phillips, Charlotte E. Willans

Research output: Contribution to journalArticle

Abstract

Silver complexes of tethered N-heterocyclic carbene-carboranyl ligands have been prepared and fully characterized. The first example of silver bonded directly to the cage of o-carborane has been identified in the solid state. The presence of a carboranyl N substituent on the N-heterocyclic carbene significantly enhances the in vitro cytotoxicity of the silver complex against HCT116 p53+/+ and HCT116 p53-/- colon cancer cells in comparison to a phenyl derivative. Conversely, the presence of a carboranyl on the backbone of a xanthine-derived N-heterocyclic carbene decreases the in vitro cytotoxicity of the silver complex in comparison to its phenyl derivative. Stability studies on the xanthine-derived ligands and complexes show that decomposition via deboronation occurs in hydrous dimethyl sulfoxide, which may attribute to the contrasting in vitro behaviors of the carborane-containing complexes.

Original languageEnglish
Pages (from-to)2530-2538
Number of pages9
JournalOrganometallics
Volume38
Issue number12
DOIs
Publication statusPublished - 7 Jun 2019

Fingerprint

carbenes
Silver
therapy
cancer
silver
xanthines
carborane
Xanthine
Cytotoxicity
Ligands
Derivatives
ligands
Dimethyl Sulfoxide
Cells
solid state
Decomposition
decomposition
carbene

Cite this

Holmes, J., Kearsey, R. J., Paske, K. A., Singer, F. N., Atallah, S., Pask, C. M., ... Willans, C. E. (2019). Tethered N-Heterocyclic Carbene-Carboranyl Silver Complexes for Cancer Therapy. Organometallics, 38(12), 2530-2538. https://doi.org/10.1021/acs.organomet.9b00228
Holmes, Jordan ; Kearsey, Rachel J. ; Paske, Katie A. ; Singer, Frances N. ; Atallah, Suliman ; Pask, Christopher M. ; Phillips, Roger M. ; Willans, Charlotte E. / Tethered N-Heterocyclic Carbene-Carboranyl Silver Complexes for Cancer Therapy. In: Organometallics. 2019 ; Vol. 38, No. 12. pp. 2530-2538.
@article{7aa75a84d7924de0805da0129aec5e4d,
title = "Tethered N-Heterocyclic Carbene-Carboranyl Silver Complexes for Cancer Therapy",
abstract = "Silver complexes of tethered N-heterocyclic carbene-carboranyl ligands have been prepared and fully characterized. The first example of silver bonded directly to the cage of o-carborane has been identified in the solid state. The presence of a carboranyl N substituent on the N-heterocyclic carbene significantly enhances the in vitro cytotoxicity of the silver complex against HCT116 p53+/+ and HCT116 p53-/- colon cancer cells in comparison to a phenyl derivative. Conversely, the presence of a carboranyl on the backbone of a xanthine-derived N-heterocyclic carbene decreases the in vitro cytotoxicity of the silver complex in comparison to its phenyl derivative. Stability studies on the xanthine-derived ligands and complexes show that decomposition via deboronation occurs in hydrous dimethyl sulfoxide, which may attribute to the contrasting in vitro behaviors of the carborane-containing complexes.",
author = "Jordan Holmes and Kearsey, {Rachel J.} and Paske, {Katie A.} and Singer, {Frances N.} and Suliman Atallah and Pask, {Christopher M.} and Phillips, {Roger M.} and Willans, {Charlotte E.}",
year = "2019",
month = "6",
day = "7",
doi = "10.1021/acs.organomet.9b00228",
language = "English",
volume = "38",
pages = "2530--2538",
journal = "Organometallics",
issn = "0276-7333",
publisher = "American Chemical Society",
number = "12",

}

Holmes, J, Kearsey, RJ, Paske, KA, Singer, FN, Atallah, S, Pask, CM, Phillips, RM & Willans, CE 2019, 'Tethered N-Heterocyclic Carbene-Carboranyl Silver Complexes for Cancer Therapy', Organometallics, vol. 38, no. 12, pp. 2530-2538. https://doi.org/10.1021/acs.organomet.9b00228

Tethered N-Heterocyclic Carbene-Carboranyl Silver Complexes for Cancer Therapy. / Holmes, Jordan; Kearsey, Rachel J.; Paske, Katie A.; Singer, Frances N.; Atallah, Suliman; Pask, Christopher M.; Phillips, Roger M.; Willans, Charlotte E.

In: Organometallics, Vol. 38, No. 12, 07.06.2019, p. 2530-2538.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Tethered N-Heterocyclic Carbene-Carboranyl Silver Complexes for Cancer Therapy

AU - Holmes, Jordan

AU - Kearsey, Rachel J.

AU - Paske, Katie A.

AU - Singer, Frances N.

AU - Atallah, Suliman

AU - Pask, Christopher M.

AU - Phillips, Roger M.

AU - Willans, Charlotte E.

PY - 2019/6/7

Y1 - 2019/6/7

N2 - Silver complexes of tethered N-heterocyclic carbene-carboranyl ligands have been prepared and fully characterized. The first example of silver bonded directly to the cage of o-carborane has been identified in the solid state. The presence of a carboranyl N substituent on the N-heterocyclic carbene significantly enhances the in vitro cytotoxicity of the silver complex against HCT116 p53+/+ and HCT116 p53-/- colon cancer cells in comparison to a phenyl derivative. Conversely, the presence of a carboranyl on the backbone of a xanthine-derived N-heterocyclic carbene decreases the in vitro cytotoxicity of the silver complex in comparison to its phenyl derivative. Stability studies on the xanthine-derived ligands and complexes show that decomposition via deboronation occurs in hydrous dimethyl sulfoxide, which may attribute to the contrasting in vitro behaviors of the carborane-containing complexes.

AB - Silver complexes of tethered N-heterocyclic carbene-carboranyl ligands have been prepared and fully characterized. The first example of silver bonded directly to the cage of o-carborane has been identified in the solid state. The presence of a carboranyl N substituent on the N-heterocyclic carbene significantly enhances the in vitro cytotoxicity of the silver complex against HCT116 p53+/+ and HCT116 p53-/- colon cancer cells in comparison to a phenyl derivative. Conversely, the presence of a carboranyl on the backbone of a xanthine-derived N-heterocyclic carbene decreases the in vitro cytotoxicity of the silver complex in comparison to its phenyl derivative. Stability studies on the xanthine-derived ligands and complexes show that decomposition via deboronation occurs in hydrous dimethyl sulfoxide, which may attribute to the contrasting in vitro behaviors of the carborane-containing complexes.

UR - http://www.scopus.com/inward/record.url?scp=85067934582&partnerID=8YFLogxK

U2 - 10.1021/acs.organomet.9b00228

DO - 10.1021/acs.organomet.9b00228

M3 - Article

VL - 38

SP - 2530

EP - 2538

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 12

ER -

Holmes J, Kearsey RJ, Paske KA, Singer FN, Atallah S, Pask CM et al. Tethered N-Heterocyclic Carbene-Carboranyl Silver Complexes for Cancer Therapy. Organometallics. 2019 Jun 7;38(12):2530-2538. https://doi.org/10.1021/acs.organomet.9b00228