The H.G. Smith Award Article: Fluorescent Analogues of NAMI-A: Synthesis, Characterisation, Fluorescent Properties, and Preliminary Biological Studies in Human Lung Cancer Cells

Sumy Antony; Jonathan C. Morris; Toby D. M. Bell; Tracey Brown; Leone Spiccia; Hugh H. Harris

doi:10.1071/CH14205

RESEARCH ARTICLE

The H.G. Smith Award Article: Fluorescent Analogues of NAMI-A: Synthesis, Characterisation, Fluorescent Properties, and Preliminary Biological Studies in Human Lung Cancer Cells

Sumy Antony ^A ^B , Jonathan C. Morris ^C , Toby D. M. Bell ^B , Tracey Brown ^D , Leone Spiccia ^B and Hugh H. Harris ^A ^E

+ Author Affiliations

- Author Affiliations

^A School of Chemistry and Physics, The University of Adelaide, Adelaide, SA 5005, Australia.

^B School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.

^C School of Chemistry, UNSW Australia, UNSW Sydney, NSW 2052, Australia.

^D Department of Biochemistry and Molecular Biology, Monash University, Clayton, Vic. 3800, Australia.

^E Corresponding author. Email: hugh.harris@adelaide.edu.au

Australian Journal of Chemistry 67(12) 1711-1717 https://doi.org/10.1071/CH14205
Submitted: 21 March 2014 Accepted: 1 May 2014 Published: 27 June 2014

Abstract

Two new fluorescent ruthenium(iii) complexes, namely 7-azaindolium trans-tetrachlorido(7-azaindole)(dimethylsulfoxide)ruthen(iii)ate (F1) and N-[histaminedihydrolium]-1,8-naphthalenecarboximidic trans-tetracholoro(dimethylsulfoxide)(N-[histaminedihydro]-1,8-naphthalenecarboximide)ruthen(iii)ate (F2) and their respective tetramethylammonium analogues (F3 and F4) are reported herein. The compounds were characterised by elemental analysis, mass spectrometry, UV-vis spectrophotometry, and fluorescence spectroscopy. Molar extinction coefficients (ϵ_max) and fluorescence emission spectra were compared to evaluate the electronic properties of the synthesised fluorescent analogues, and hence their value as intracellular fluorescence probes. F3 and F4 were synthesised and characterised in order to eliminate fluorescence arising from the counter-cations in F1 and F2 and thus to obtain a fluorescence quantum yield that reflects only a contribution from the metal complex anion. Half-inhibitory concentrations (IC₅₀) were determined for A549 cells exposed to the Ru complexes for 24 h: F3 (203 ± 26 μM) and F4 (185 ± 20 μM).

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The H.G. Smith Award Article: Fluorescent Analogues of NAMI-A: Synthesis, Characterisation, Fluorescent Properties, and Preliminary Biological Studies in Human Lung Cancer Cells

Abstract

References

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