Doctor Christopher Gordon

Senior Lecturer in Chemistry, Organic,
Physical Sciences

Biography
Contact
Publications
Projects
Supervision
Teaching

Biography

On the successful completion of my PhD studies at the University of Wollongong in 2007 which focused on the development of compounds which inhibit HIV, I commenced a postdoctoral fellowship at the University of Newcastle. Although the primary focus of this three-year tenure was the development of anti-parasitic drugs for the livestock industry, a substantial emphasis was also placed on devising efficient and greener synthetic methodologies to reduce the environmental impacts of synthetic chemistry. These investigations included developing solvent free reactions, multi-component reactions, and the replacement of volatile organic solvents with environmentally friendly equivalents such as ionic liquids. Additionally I was afforded the opportunity to play a key role in establishing the University of Newcastle flow chemistry facility were we devised a number of novel applications for new flow chemical reactors.

In early 2010 I embarked on an international posting as a senior postdoctoral fellow at the University of Nottingham Centre for Biomolecular Sciences UK under the guidance of Professor Paul Williams and Associate Professor Weng Chan. Here our research efforts focused on the development of next generation antibiotics which function by inhibiting bacterial quorum sensing. This scrambling of bacterial communication significantly reduces the virulence of a number of dangerous superbugs including S. aureus. Additionally quorum sensing inhibiting molecules are typically non-lethal to bacteria and thus it is anticipated will be less likely to drive the evolution of resistance. Our research efforts culminated in the development of a number of S. aureus antibiotics displaying sub-nanomolar activity and we are continuing the development of these molecules towards the clinic.

In 2012 I returned to Australia to establish an independent research career as university research fellow at the University of Newcastle were I continued my research interests of developing next generation antibiotics, anti-cancer agents, and the development molecular probes to study post-translational protein modifications such as protein phosphorylation.

In 2013 I was awarded an ARC DECRA fellowship to focuses on our continued development of flow-chemistry methodologies. Flow reactors are tubular or chip-based systems in which reagent streams are continuously pumped through reaction chambers and/or columns containing solid-supported reagents and chemical scavengers. Compared to tradition batch chemistry processing, the advantages of flow chemistry are numerous and include faster reactions, cleaner products, safer reactions, quick reaction optimisation, easy scale-up, and the integration of typically separate processes such as work-up and analysis. The all-encompassing aim of this research is to devise cutting-edge multi-step total-flow-synthesis methodologies which are highly versatile, robust, and pertinent to the wider synthetic community.

In 2014 I was privileged to establish an academic career at the University of Western Sydney of as lecturer of organic and medicinal chemistry. Here our current research focuses on utilising our flow chemistry methodologies to drive our medicinal chemistry programs which are gear towards the development of antibacterial compounds, radiopharmaceuticals, cancer supressing agents, and molecular probes to study post-translation protein modifications. For our recent publications go to: http://www.researcherid.com/rid/D-1135-2012.

This information has been contributed by Doctor Gordon.

Qualifications

PhD University of Wollongong
BMedChem (Hons) University of Wollongong

Awards

ARC DECRA 2012-11-05

Interests

Anit-Cancer Agents
Antibacterial Agents
Bacterial Quorum Sensing
Flow Chemistry

Organisational Unit (School / Division)

Physical Sciences

Contact

Email:	C.Gordon@westernsydney.edu.au
Phone:	(02) 4620 3201
Mobile:
Location:	21.1.73 CampbelltownCampbelltown

PLEASE NOTE: obtaining information from this Directory must be for the legitimate purposes of doing business with and within Western Sydney University, and must not be used for unsolicited bulk e-mailing (spamming) or similar purposes.

Teaching

Previous Teaching Areas

300876 Organic Chemistry, 2017
300891 Advanced Medicinal Chemistry, 2017
300906 Advanced Organic Chemistry, 2017

Publications

Journal Articles

Aputen, A., Elias, M., Gilbert, J., Sakoff, J., Gordon, C., Scott, K. and Aldrich-Wright, J. (2023), 'Versatile platinum(IV) prodrugs of naproxen and acemetacin as chemo-anti-inflammatory agents', Cancers, vol 15, no 9 .
McGhie, B., Sakoff, J., Gilbert, J., Gordon, C. and Aldrich-Wright, J. (2023), 'Synthesis and characterisation of fluorescent novel pt(II) cyclometallated complexes with anticancer activity', International Journal of Molecular Sciences, vol 24, no 9 .
Menti-Platten, M., Aldrich-Wright, J. and Gordon, C. (2022), 'A flow-based transition-metal-catalysed hydrogenolysis strategy to facilitate peptide side-chain deprotection', Organic and Biomolecular Chemistry, vol 20, no 1 , pp 106 - 112.
Tadros, J., Dankers, C., Jurisinec, A., Menti-Platten, M., Aldrich-Wright, J. and Gordon, C. (2022), 'A comparison of immobilised triphenylphosphine and 1-hydroxybenzotriazole as mediators of catch-and-release acylation under flow conditions', Chemistry: An Asian Journal, vol 17, no 5 .
Khoury, A., Sakoff, J., Gilbert, J., Scott, K., Karan, S., Gordon, C. and Aldrich-Wright, J. (2022), 'Cyclooxygenase-inhibiting platinum(IV) prodrugs with potent anticancer activity', Pharmaceutics, vol 14, no 4 .
Aputen, A., Elias, M., Gilbert, J., Sakoff, J., Gordon, C., Scott, K. and Aldrich-Wright, J. (2022), 'Potent chlorambucil-platinum(IV) prodrugs', International Journal of Molecular Sciences, vol 23, no 18 .
McGhie, B., Sakoff, J., Gilbert, J., Gordon, C. and Aldrich-Wright, J. (2022), 'Novel planar Pt(II) cyclometallated cytotoxic complexes with G-quadruplex stabilisation and luminescent properties', International Journal of Molecular Sciences, vol 23, no 18 .
Khoury, A., Sakoff, J., Gilbert, J., Karan, S., Gordon, C. and Aldrich-Wright, J. (2022), 'Potent platinum(IV) prodrugs that incorporate a biotin moiety to selectively target cancer cells', Pharmaceutics, vol 14, no 12 .
Khoury, A., Elias, E., Mehanna, S., Shebaby, W., Deo, K., Mansour, N., Khalil, C., Sayyed, K., Sakoff, J., Gilbert, J., Daher, C., Gordon, C., Taleb, R. and Aldrich-Wright, J. (2022), 'Novel platinum(II) and platinum(IV) antitumor agents that exhibit potent cytotoxicity and selectivity', Journal of Medicinal Chemistry, vol 65, no 24 , pp 16481 - 16493.
Tadros, J., Dankers, C., Aldrich-Wright, J., Polyzos, A. and Gordon, C. (2021), 'A solid-phase assisted flow approach to in situ Wittig-type olefination coupling', European Journal of Organic Chemistry, vol 2021, no 29 , pp 4184 - 4194.
Horswill, A. and Gordon, C. (2020), 'Structure-activity-relationship studies of small molecule modulators of the staphylococcal accessory gene regulator', Journal of Medicinal Chemistry, vol 63, no 6 , pp 2705 - 2730.
Gordon, C. (2020), 'Synthetic strategies to access staphylococcus auto-inducing peptides as quorum sensing modulators', Organic and Biomolecular Chemistry, vol 18, no 3 , pp 379 - 390.
Dankers, C., Tadros, J., Harman, D., Aldrich-Wright, J., Nguyen, T. and Gordon, C. (2020), 'Immobilized carbodiimide assisted flow combinatorial protocol to facilitate amide coupling and lactamization', ACS Combinatorial Science, vol 22, no 5 , pp 255 - 267.
Bjelosevic, A., Sakoff, J., Gilbert, J., Zhang, Y., Gordon, C. and Aldrich-Wright, J. (2020), 'Synthesis, characterisation, and biological activity of the ruthenium complexes of the N4-Tetradentate (N4-TL), 1,6-Di(2'-pyridyl)-2,5-dimethyl-2,5-diazahexane (picenMe2)', Australian Journal of Chemistry, vol 73, no 10 , pp 956 - 968.
Hillenbrand, J., Leutzsch, M., Yiannakas, E., Gordon, C., Wille, C., Noothling, N., Copeeret, C. and Fu?rstner, A. (2020), '"Canopy catalysts" for alkyne metathesis : molybdenum alkylidyne complexes with a tripodal ligand framework', Journal of the American Chemical Society, vol 142, no 25 , pp 11279 - 11294.
Venkatesh, A., Lund, A., Rochlitz, L., Jabbour, R., Gordon, C., Menzildjian, G., Viger-Gravel, J., Berruyer, P., Gajan, D., Coperet, C., Lesage, A. and Rossini, A. (2020), 'The structure of molecular and surface platinum sites determined by DNP-SENS and fast MAS 195Pt solid-state NMR spectroscopy', Journal of the American Chemical Society, vol 142, no 44 , pp 18936 - 18945.
Gordon, C., Engler, H., Tragl, A., Plodinec, M., Lunkenbein, T., Berkessel, A., Teles, J., Parvulescu, A. and Coperet, C. (2020), 'Efficient epoxidation over dinuclear sites in titanium silicalite-1', Nature, vol 586 , pp 708 - 713.
Hizartzidis, L., Gilbert, J., Gordon, C., Sakoff, J. and McCluskey, A. (2019), 'Synthesis and cytotoxicity of octahydroepoxyisoindole-7-carboxylic acids and norcantharidin-amide hybrids as norcantharidin analogues', ChemMedChem, vol 14, no 12 , pp 1152 - 1161.
Spare, L., Menti, M., Harman, D., Aldrich-Wright, J. and Gordon, C. (2019), 'A continuous flow protocol to generate, regenerate, load, and recycle chlorotrityl functionalised resins', Reaction Chemistry and Engineering, vol 4, no 7 , pp 1309 - 1317.
Deo, K., Ang, D., McGhie, B., Rajamanickam, A., Dhiman, A., Khoury, A., Holland, J., Bjelosevic, A., Pages, B., Gordon, C. and Aldrich-Wright, J. (2018), 'Platinum coordination compounds with potent anticancer activity', Coordination Chemistry Reviews, vol 375 , pp 148 - 163.
Gordon, C. (2018), 'The renascence of continuous-flow peptide synthesis : an abridged account of solid and solution-based approaches', Organic and Biomolecular Chemistry, vol 16, no 2 , pp 180 - 196.
Spare, L., Harman, D., Aldrich-Wright, J., Nguyen, T. and Gordon, C. (2018), 'Chemoselective flow hydrogenation approaches to diversify the cytotoxic tetrahydroepoxyisoindole carboxamide scaffold', Advanced Synthesis and Catalysis, vol 360, no 6 , pp 1209 - 1217.
Gordon, C., Dalton, N., Vandegraaff, N., Deadman, J., Rhodes, D., Coates, J., Pyne, S., Griffith, R., Bremner, J. and Keller, P. (2018), 'A structure-based design approach to advance the allyltyrosine-based series of HIV integrase inhibitors', Tetrahedron, vol 74, no 12 , pp 1253 - 1268.
Spare, L., Laude, V., Harman, D., Aldrich-Wright, J. and Gordon, C. (2018), 'An optimised approach for continuous-flow solid-phase peptide synthesis utilising a rudimentary flow reactor', Reaction Chemistry and Engineering, vol 3, no 6 , pp 875 - 882.
Pucino, M., Inoue, M., Gordon, C., Schowner, R., Stohr, L., Sen, S., Hegedus, C., Robe, E., Toth, F., Buchmeiser, M. and Coperet, C. (2018), 'Promoting terminal olefin metathesis with a supported cationic molybdenum imido alkylidene n-heterocyclic carbene catalyst', Angewandte Chemie (International Edition), vol 57, no 44 , pp 14566 - 14569.
Gordon, C., Eldridge, D., Ripple, W., Crowther, M., Moore, B. and Letnic, M. (2017), 'Shrub encroachment is linked to extirpation of an apex predator', Journal of Animal Ecology, vol 86, no 1 , pp 147 - 157.
Spare, L., Falsetta, P., Gilbert, J., Harman, D., Baker, M., Li, F., McCluskey, A., Clegg, J., Sakoff, J., Aldrich-Wright, J. and Gordon, C. (2017), 'Cytotoxicity of a series of norcantharidin-inspired tetrahydroepoxyisoindole carboxamides', ChemMedChem, vol 12, no 2 , pp 130 - 145.
Gordon, C., Moore, B. and Letnic, M. (2017), 'Temporal and spatial trends in the abundances of an apex predator, introduced mesopredator and ground-nesting bird are consistent with the mesopredator release hypothesis', Biodiversity and Conservation, vol 26, no 6 , pp 1445 - 1462.
Trinh, T., McLaughlin, E., Gordon, C., Bernstein, I., Pye, V., Redgrove, K. and McCluskey, A. (2017), 'Small molecule Hedgehog pathway antagonists', Organic and Biomolecular Chemistry, vol 15, no 14 , pp 3046 - 3059.
Tran, U., Hock, K., Gordon, C., Koenigs, R. and Nguyen, T. (2017), 'Efficient phosphine-mediated formal C(sp3)-C(sp3) coupling reactions of alkyl halides in batch and flow', Chemical Communications, vol 36 , pp 4950 - 4953.
Cossar, P., Abdel-Hamid, M., Ma, C., Sakoff, J., Trinh, T., Gordon, C., Lewis, P. and McCluskey, A. (2017), 'Small-molecule inhibitors of the NusB-NusE protein-protein interaction with antibiotic activity', ACS Omega, vol 2, no 7 , pp 3839 - 3857.
Cossar, P., Ma, C., Gordon, C., Ambrus, J., Lewis, P. and McCluskey, A. (2017), 'Identification and validation of small molecule modulators of the NusB-NusE interaction', Bioorganic and Medicinal Chemistry Letters, vol 27, no 2 , pp 162 - 167.
Gordon, C., Yamamoto, K., Liao, W., Allouche, F., Andersen, R., Coperet, C., Raynaud, C. and Eisenstein, O. (2017), 'Metathesis activity encoded in the metallacyclobutane carbon-13 NMR chemical shift tensors', ACS Central Science, vol 3, no 7 , pp 759 - 768.
Trinh, T., McLaughlin, E., Abdel-Hamid, M., Gordon, C., Bernstein, I., Pye, V., Cossar, P., Sakoff, J. and McCluskey, A. (2016), 'Quinolone-1-(2H)-ones as hedgehog signalling pathway inhibitors', Organic and Biomolecular Chemistry, vol 14, no 26 , pp 6304 - 6315.
Gordon, C., Olson, S., Lister, J., Kavanaugh, J. and Horswill, A. (2016), 'Truncated auto-inducing peptides as antagonists of Staphylococcus lugdunensis quorum sensing', Journal of Medicinal Chemistry, vol 59, no 19 , pp 8879 - 8888.
Deo, K., Pages, B., Ang, D., Gordon, C. and Aldrich-Wright, J. (2016), 'Transition metal intercalators as anticancer agents : recent advances', International Journal of Molecular Sciences, vol 17, no 11 .
Baker, M., Weinberg, A., Hetherington, L., Villaverde, A., Velkov, T., Baell, J. and Gordon, C. (2015), 'Defining the mechanisms by which the reactive oxygen species by-product, 4-hydroxynonenal, affects human sperm cell function', Biology of Reproduction, vol 92, no 4 , pp 1 - 10.
Cossar, P., Hizartzidis, L., Simone, M., McCluskey, A. and Gordon, C. (2015), 'The expanding utility of continuous flow hydrogenation', Organic and Biomolecular Chemistry, vol 13, no 26 , pp 7119 - 7130.
Trinh, T., McLaughlin, E., Gordon, C. and McCluskey, A. (2014), 'Hedgehog signalling pathway inhibitors as cancer suppressing agents', MedChemComm, vol 5, no 2 , pp 117 - 133.
Gordon, C., Hizartzidis, L., Tarleton, M., Sakoff, J., Gilbert, J., Campbell, B., Gasser, R. and McCluskey, A. (2014), 'Discovery of acrylonitrile-based small molecules active against Haemonchus contortus', MedChemComm, vol 5, no 2 , pp 159 - 164.
Trinh, T., Hizartzidis, L., Lin, A., Harman, D., McCluskey, A. and Gordon, C. (2014), 'An efficient continuous flow approach to furnish furan-based biaryls', Organic and Biomolecular Chemistry, vol 12, no 47 , pp 9562 - 9571.
Hizartzidis, L., Cossar, P., Robertson, M., Simone, M., Young, K., McCluskey, A. and Gordon, C. (2014), 'Expanding the utility of flow hydrogenation : a robust protocol restricting hydrodehalogenation', RSC Advances: An International Journal to Further the Chemical Sciences, vol 4, no 100 , pp 56743 - 56748.
Gordon, C., Williams, P. and Chan, W. (2013), 'Attenuating Staphylococcus aureus virulence gene regulation : a medicinal chemistry perspective', Journal of Medicinal Chemistry, vol 56, no 4 , pp 1389 - 1404.
Gordon, C., Venn-Brown, B., Robertson, M., Young, K., Chau, N., Mariana, A., Whiting, A., Chircop, M., Robinson, P. and McCluskey, A. (2013), 'Development of second-generation indole-based dynamin GTPase inhibitors', Journal of Medicinal Chemistry, vol 56, no 1 , pp 46 - 59.
Letnic, M., Greenville, A., Denny, E., Dickman, C., Tischler, M., Gordon, C. and Koch, F. (2011), 'Does a top predator suppress the abundance of an invasive mesopredator at a continental scale?', Global Ecology and Biogeography, vol 20, no 2 , pp 343 - 353.
Gordon, C., Young, K., Robertson, M., Hill, T. and McCluskey, A. (2011), 'An Ugi-intramolecular Diels-Alder route to highly substituted tetrahydroepoxyisoindole carboxamides', Tetrahedron, vol 67, no 2 , pp 554 - 561.
Campbell, B., Tarleton, M., Gordon, C., Sakoff, J., Gilbert, J., McCluskey, A. and Gasser, R. (2011), 'Norcantharidin analogues with nematocidal activity in Haemonchus contortus', Bioorganic and Medicinal Chemistry Letters, vol 21, no 11 , pp 3277 - 3281.
Wright, A., McCluskey, A., Robertson, M., MacGregor, K., Gordon, C. and Guenther, J. (2011), 'Anti-malarial, anti-algal, anti-tubercular, anti-bacterial, anti-photosynthetic, and anti-fouling activity of diterpene and diterpene isonitriles from the tropical marine sponge Cymbastela hooperi', Organic and Biomolecular Chemistry, vol 9, no 2 , pp 400 - 407.
Gordon, C., Young, K., Hizartzidis, L., Deane, F. and McCluskey, A. (2011), 'Investigation of the one-pot synthesis of quinolin-2-(1H)-ones and the discovery of a variation of the three-component Ugi reaction', Organic and Biomolecular Chemistry, vol 9, no 5 , pp 1419 - 1428.
Tarleton, M., Young, K., Unicomb, E., McCluskey, S., Robertson, M., Gordon, C. and McCluskey, A. (2011), 'A flow chemistry approach to norcantharidin analogues', Letters in Drug Design and Discovery, vol 8, no 6 , pp 568 - 574.
Chircop, M., Perera, S., Mariana, A., Lau, H., Ma, M., Gilbert, J., Jones, N., Gordon, C., Young, K., Morokoff, A., Sakoff, J., O'Brien, T., McCluskey, A. and Robinson, P. (2011), 'Inhibition of dynamin by dynole 34-2 induces cell death following cytokinesis failure in cancer cells', Molecular Cancer Therapeutics, vol 10, no 9 , pp 1553 - 1562.
Robertson, M., Gordon, C., Gilbert, J., McCluskey, A. and Sakoff, J. (2011), 'Norcantharimide analogues possessing terminal phosphate esters and their anti-cancer activity', Bioorganic and Medicinal Chemistry, vol 19, no 18 , pp 5734 - 5741.
Joshi, S., Perera, S., Gilbert, J., Smith, C., Mariana, A., Gordon, C., Sakoff, J., McCluskey, A., Robinson, P., Braithwaite, A. and Chircop, M. (2010), 'The dynamin inhibitors MiTMAB and OcTMAB induce cytokinesis failure and inhibit cell proliferation in human cancer cells', Molecular Cancer Therapeutics, vol 9, no 7 , pp 1995 - 2006.
Chircop, M., Malladi, C., Lian, A., Page, S., Zavortink, M., Gordon, C., McCluskey, A. and Robinson, P. (2010), 'Calcineurin activity is required for the completion of cytokinesis', Cellular and Molecular Life Sciences, vol 67, no 21 , pp 3725 - 3737.
Odell, L., Howan, D., Gordon, C., Robertson, M., Chau, N., Mariana, A., Whiting, A., Abagyan, R., Daniel, J., Gorgani, N., Robinson, P. and McCluskey, A. (2010), 'The pthaladyns : GTP competitive inhibitors of dynamin I and II GTPase derived from virtual screening', Journal of Medicinal Chemistry, vol 53, no 14 , pp 5267 - 5280.
Bajsa, J., McCluskey, A., Gordon, C., Stewart, S., Hill, T., Sahu, R., Duke, S. and Tekwani, B. (2010), 'The antiplasmodial activity of norcantharidin analogs', Bioorganic and Medicinal Chemistry Letters, vol 20, no 22 , pp 6688 - 6695.
Gordon, C., Byrne, N. and McCluskey, A. (2010), 'A facile, protic ionic liquid route to N-substituted 5-hydroxy-4-methyl-3- oxoisoindoline-1-carboxamides and N-substituted 3-oxoisoindoline-4-carboxylic acids', Green Chemistry, vol 12, no 6 , pp 1000 - 1006.
Hill, T., Mariana, A., Gordon, C., Odell, L., Robertson, M., McGeachie, A., Chau, N., Daniel, J., Gorgani, N., Robinson, P. and McCluskey, A. (2010), 'Iminochromene inhibitors of dynamins I and II GTPase activity and endocytosis', Journal of Medicinal Chemistry, vol 53, no 10 , pp 4094 - 4102.
Zayas, H., Bowyer, M., Gordon, C., Holdsworth, C. and McCluskey, A. (2009), 'Synthesis of biaryl-styrene monomers by microwave-assisted Suzuki coupling', Tetrahedron Letters, vol 50, no 43 , pp 5894 - 5895.
Hill, T., Gordon, C., McGeachie, A., Venn-Brown, B., Odell, L., Chau, N., Quan, A., Mariana, A., Sakoff, J., Chircop, M., Robinson, P. and McCluskey, A. (2009), 'Inhibition of dynamin mediated endocytosis by the dynoles : synthesis and functional activity of a family of indoles', Journal of Medicinal Chemistry, vol 52, no 12 , pp 3762 - 3773.
Hill, T., Stewart, S., Gordon, C., Ackland, S., Gilbert, J., Sauer, B., Sakoff, J. and McCluskey, A. (2008), 'Norcantharidin analogues : synthesis, anticancer activity and protein phosphatase 1 and 2A inhibition', ChemMedChem, vol 3, no 12 , pp 1878 - 1892.

<a href="https://orcid.org/0000-0001-7583-5609" target="orcid.widget" rel="noopener noreferrer" style="vertical-align:top;"><img src="https://orcid.org/sites/default/files/images/orcid_16x16.png" style="width:1em;margin-right:.5em;" alt="ORCID iD icon">orcid.org/0000-0001-7583-5609</a>