Towards Water Soluble Mitochondria-Targeting Theranostic Osmium(II) Triazole-Based Complexes

Salem A E Omar, Paul A. Scattergood, Luke K. McKenzie, Helen E. Bryant, Julia A. Weinstein, Paul I P Elliott

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The complex [Os(btzpy)2][PF6]2 (1, btzpy = 2,6-bis(1-phenyl-1,2,3-Triazol-4-yl)pyridine) has been prepared and characterised. Complex 1 exhibits phosphorescence (λem = 595 nm, τ = 937 ns, φem = 9.3% in degassed acetonitrile) in contrast to its known ruthenium(II) analogue, which is non-emissive at room temperature. The complex undergoes significant oxygen-dependent quenching of emission with a 43-fold reduction in luminescence intensity between degassed and aerated acetonitrile solutions, indicating its potential to act as a singlet oxygen sensitiser. Complex 1 underwent counterion metathesis to yield [Os(btzpy)2]Cl2 (1Cl), which shows near identical optical absorption and emission spectra to those of 1. Direct measurement of the yield of singlet oxygen sensitised by 1Cl was carried out (φ(1O2) = 57%) for air equilibrated acetonitrile solutions. On the basis of these photophysical properties, preliminary cellular uptake and luminescence microscopy imaging studies were conducted. Complex 1Cl readily entered the cancer cell lines HeLa and U2OS with mitochondrial staining seen and intense emission allowing for imaging at concentrations as low as 1 μM. Long-Term toxicity results indicate low toxicity in HeLa cells with LD50 >100 μM. Osmium(II) complexes based on 1 therefore present an excellent platform for the development of novel theranostic agents for anticancer activity.

Original languageEnglish
Article number1382
Number of pages12
JournalMolecules
Volume21
Issue number10
DOIs
Publication statusPublished - 18 Oct 2016

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Osmium
Mitochondria
Triazoles
mitochondria
osmium
acetonitrile
Singlet Oxygen
Luminescence
toxicity
Toxicity
Water
oxygen
luminescence
water
Imaging techniques
Phosphorescence
Ruthenium
metathesis
Lethal Dose 50
staining

Cite this

Omar, Salem A E ; Scattergood, Paul A. ; McKenzie, Luke K. ; Bryant, Helen E. ; Weinstein, Julia A. ; Elliott, Paul I P. / Towards Water Soluble Mitochondria-Targeting Theranostic Osmium(II) Triazole-Based Complexes. In: Molecules. 2016 ; Vol. 21, No. 10.
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Towards Water Soluble Mitochondria-Targeting Theranostic Osmium(II) Triazole-Based Complexes. / Omar, Salem A E; Scattergood, Paul A.; McKenzie, Luke K.; Bryant, Helen E.; Weinstein, Julia A.; Elliott, Paul I P.

In: Molecules, Vol. 21, No. 10, 1382, 18.10.2016.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Towards Water Soluble Mitochondria-Targeting Theranostic Osmium(II) Triazole-Based Complexes

AU - Omar, Salem A E

AU - Scattergood, Paul A.

AU - McKenzie, Luke K.

AU - Bryant, Helen E.

AU - Weinstein, Julia A.

AU - Elliott, Paul I P

PY - 2016/10/18

Y1 - 2016/10/18

N2 - The complex [Os(btzpy)2][PF6]2 (1, btzpy = 2,6-bis(1-phenyl-1,2,3-Triazol-4-yl)pyridine) has been prepared and characterised. Complex 1 exhibits phosphorescence (λem = 595 nm, τ = 937 ns, φem = 9.3% in degassed acetonitrile) in contrast to its known ruthenium(II) analogue, which is non-emissive at room temperature. The complex undergoes significant oxygen-dependent quenching of emission with a 43-fold reduction in luminescence intensity between degassed and aerated acetonitrile solutions, indicating its potential to act as a singlet oxygen sensitiser. Complex 1 underwent counterion metathesis to yield [Os(btzpy)2]Cl2 (1Cl), which shows near identical optical absorption and emission spectra to those of 1. Direct measurement of the yield of singlet oxygen sensitised by 1Cl was carried out (φ(1O2) = 57%) for air equilibrated acetonitrile solutions. On the basis of these photophysical properties, preliminary cellular uptake and luminescence microscopy imaging studies were conducted. Complex 1Cl readily entered the cancer cell lines HeLa and U2OS with mitochondrial staining seen and intense emission allowing for imaging at concentrations as low as 1 μM. Long-Term toxicity results indicate low toxicity in HeLa cells with LD50 >100 μM. Osmium(II) complexes based on 1 therefore present an excellent platform for the development of novel theranostic agents for anticancer activity.

AB - The complex [Os(btzpy)2][PF6]2 (1, btzpy = 2,6-bis(1-phenyl-1,2,3-Triazol-4-yl)pyridine) has been prepared and characterised. Complex 1 exhibits phosphorescence (λem = 595 nm, τ = 937 ns, φem = 9.3% in degassed acetonitrile) in contrast to its known ruthenium(II) analogue, which is non-emissive at room temperature. The complex undergoes significant oxygen-dependent quenching of emission with a 43-fold reduction in luminescence intensity between degassed and aerated acetonitrile solutions, indicating its potential to act as a singlet oxygen sensitiser. Complex 1 underwent counterion metathesis to yield [Os(btzpy)2]Cl2 (1Cl), which shows near identical optical absorption and emission spectra to those of 1. Direct measurement of the yield of singlet oxygen sensitised by 1Cl was carried out (φ(1O2) = 57%) for air equilibrated acetonitrile solutions. On the basis of these photophysical properties, preliminary cellular uptake and luminescence microscopy imaging studies were conducted. Complex 1Cl readily entered the cancer cell lines HeLa and U2OS with mitochondrial staining seen and intense emission allowing for imaging at concentrations as low as 1 μM. Long-Term toxicity results indicate low toxicity in HeLa cells with LD50 >100 μM. Osmium(II) complexes based on 1 therefore present an excellent platform for the development of novel theranostic agents for anticancer activity.

KW - Anticancer

KW - Complexes

KW - Ligands

KW - Osmium

KW - Oxygen Sensitizer

KW - Photophysics

KW - Triazole

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DO - 10.3390/molecules21101382

M3 - Article

VL - 21

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 10

M1 - 1382

ER -