Dr Neil Donoghue

Dr. Neil Donoghue is a Research Fellow in the Phenomics and Bioinformatics Research Centre (PBRC) at the University of South Australia. He is currently working with Associate Prof­essor Desmond Lun in a project to produce fuel from micro-organisms.

He completed his B.Sc. in 1990 with a double major in chemistry (Organic Chemistry; Physical & Inorganic Chemistry) from the University of Adelaide, Australia, and received his B.Sc.(Hons) (in Physical & Inorganic Chemistry) the following year from the same university. In 1998, he obtained his Ph.D. (in Organic Chemistry) from the University of New South Wales (UNSW), Australia, entitled: Aspects of Reductive Methods in Organo­phos­phorus Chemistry.

Prior to his present position, Dr. Donoghue worked in Sydney as a post doctoral fellow with Prof­essor Philip Hogg in the Centre for Vascular Research, UNSW (now called the UNSW Cancer Research Centre), and the Children’s Cancer Institute Australia (CCIA), where he designed and synthesised a novel arsenical, 4-(N-(S-gluta­thionyl­acetyl)­amino)­phenyl­arsonous acid (GSAO; see figure below). GSAO has a very low toxicity, unusual for arsenicals, and has shown promising activity in areas as diverse as cancer, HIV infection, and arthritis. It is currently under­going phase I/II human clinical trials as an anti-cancer agent. Dr. Donoghue has also co-authored a patent on GSAO with Prof­essor Hogg.

His Ph.D. studies (under Associate Prof­essor Michael J. Gallagher) involved the pre­paration of new examples of tetra­organo­hydro­phos­phoranes, R4PH, (R = phenyl, methyl), and the discovery of two entirely new classes of compounds, the tri­organo­dihydro­phos­phoranes, R3PH2, and the ionic lithium tetra­organo­dihydro­phos­phoranates, Li[R4PH2]. The reaction used to generate these new species is based on the standard method of LiAlH4 reduction of quaternary phos­phonium salts giving tertiary phos­phines (which are themselves important industrial catalysts). In fact, these new species are the inter­mediates of this reaction, and Dr. Donoghue has proposed a mechanism accounting for this which is consistent with all observations made during the project. Shown below are Ph4PH, Ph3PH2, and Li[Ph4PH2] (where Ph = phenyl), all of which were unknown prior to this work (the uncharged species are thought to be fluxional, a feature of AB5 molecules, and so are not presumed to be fixed necessarily in the stereo­chemical arrange­ments depicted; the stereo­chemistry of the anion is depicted as the trans isomer, but its actual stereo­chemistry is unknown):

Under the supervision of Dr. Edward R. T. Tiekink, his Honours project involved the synthesis and character­isation of fifteen diorgano­tin(IV) bis(xanthates), [R2Sn(S2COR’)2], two of which were also character­ised by single crystal X-ray structure deter­mination (R = phenyl; R' = ethyl, iso-propyl; see below - hydrogen atoms not shown, carbon atoms not labelled). Some organo­tin(IV) compounds have been shown by others to exhibit anti-tumour activity, and testing of the compounds prepared in this project showed that some did have such activity, comparable to that of cis-platin.

Dr. Donoghue has experience teaching laboratory classes at under­graduate level at both the University of Adelaide (1st year inorganic and physical chemistry: 1991) and UNSW (1st year chemistry, and organic chemistry up to 3rd year level: 1992-1998). He has taught basic chemistry courses at TafeSA (Gilles Plains campus, Adelaide), and has also privately tutored chemistry at both undergraduate and high school levels, as well as mathematics at high school level.

B.Sc.(Hons)-Adelaide, Ph.D.-UNSW.

Journal Articles:

Anthony S. Don, Oliver Kisker, Pierre Dilda, Neil Donoghue, Xueyun Zhao, Stephanie Decollogne, Belinda Creighton, Evelyn Flynn, Judah Folkman, and Philip J. Hogg, “A peptide trivalent arsenical inhibits tumor angio­genesis by perturbing mito­chondrial function in angiogenic endothelial cells.” Cancer Cell (2003) 3(5) 497-509.

Lisa J. Matthias, Patricia T. W. Yam, Xing-Mai Jiang, Nick Vandegraaff, Peng Li, Pantelis Poumbourios, Neil Donoghue, and Philip J. Hogg, “Disulfide exchange in domain 2 of CD4 is required for entry of HIV-1.” Nature Immunology (2002) 3(8) 727-732.

Neil Donoghue, Patricia T. W. Yam, Xing-Mai Jiang, and Philip J. Hogg, “Presence of closely spaced protein thiols on the surface of mammalian cells.” Protein Science (2000) 9(12) 2436-2445.

Neil Donoghue and Michael J. Gallagher, “Multiple pathways in the cleavage of benzyl groups from phosphonium salts by lithium aluminium hydride.” Chemical Communications (1998) (18) 1973-1974.

Neil Donoghue and Michael J. Gallagher, “Mono- and dihydro­phosphoranes and dihydro­phosphoranates as intermediates in the reaction of phosphonium salts with LiAlH4.” Phosphorus, Sulfur and Silicon and the Related Elements (1997) 123(1) 169-173.

Neil Donoghue, Edward R. T. Tiekink, and Lorraine Webster, “Synthesis, character­iza­tion and in vitro anti­tumor activity of diorgano­tin bis­xan­thates [R2Sn(S2COR')2] (R = Me, Et, Bu, Ph; R' = Et, CHMe2, cHex) and crystal structure of bis(O-ethyl­di­thio­car­bon­ato)­di­phenyl­tin(IV).” Applied Organo­metal­lic Chem­is­try (1993) 7(2) 109-117.

Neil Donoghue and Edward R. T. Tiekink, “Crystal structure of bis(O-iso-propyl­di­thio­car­bon­ato)­di­phenyl­tin(IV).” Journal of Organo­metal­lic Chem­is­try (1991) 420(2) 179-184.

Book Articles:

Philip J. Hogg and Neil Donoghue “Identifi­cation of redox-active proteins on cell surface.” Methods in Enzymology (2002) 352 (Redox Cell Biology and Genetics, Part A) 101-112.

Philip J. Hogg and Neil Donoghue “Characteri­zation of redox-active proteins on cell surface.” Methods in Enzymology (2002) 348 (Protein Sensors and Reactive Oxygen Species, Part B) 76-86.

Other Articles (not Peer-Reviewed):

Neil Donoghue “A novel chemistry to treat cancer.” Chaos Magazine (Science @ UNSW) (2001) (20) 12 (Editor: Mary Mulcahy).

Patents (GSAO):

Philip John Hogg and Neil Donoghue “Substan­tially cell membrane impermeable compound and use thereof.” US Patent 7498406 (issued on March 3, 2009).

Philip John Hogg and Neil Donoghue “Substan­tially cell membrane impermeable compound and use thereof.” US Patent 7074766 (issued on July 11, 2006).

Conferences & Presentations:

University of New South Wales (UNSW), School of Chemistry: Inter-Faculty Invited Speaker, 9 December 2004, Kensington, Sydney, NSW, Australia.
Oral presentation: Neil Donoghue, “GSAO: A Non-Toxic Trivalent Arsenical.”

International Union of Pure and Applied Chemistry (IUPAC): 39th Congress/Canadian Society for Chemistry: 86th Conference (theme: Chemistry at the Interfaces), 10-15 August 2003, Westin Hotel & Ottawa Congress Centre, Ottawa, Ontario, Canada.
Oral presentation: Neil Donoghue, “Inhibition of HIV Infection by an Organo­arsenical of Low Toxicity.”

International Union of Pure and Applied Chemistry (IUPAC): 14th International Conference on Organic Synthesis (ICOS-14), 14-19 July 2002, Christchurch, New Zealand.
Poster presentation: Neil Donoghue, Anthony Don, Kevin Camphausen, Belinda Creighton, and Philip J. Hogg, “In Vivo Imaging of Tumours using Fluorescently Labeled Arsenicals.”

International Union of Pure and Applied Chemistry (IUPAC): 38th Congress/World Chemistry Congress/Asian Federation for Medicinal Chemistry (AFMC) International Medicinal Chemistry Symposium (AIMECS-01), 1-6 July 2001, Brisbane Convention & Exhibition Centre, South Brisbane (South Bank), Brisbane, Qld, Australia.
Poster presentation: Neil Donoghue, Lisa J. Matthias, Patricia T. W. Yam, Xing-Mai Jiang, and Philip J. Hogg, “Inhibition of HIV Infection by an Organo­arsenical of Low Toxicity.”

Royal Society of Chemistry (RSC): 6th International Symposium on Applied Bioinorganic Chemistry (ISABC-6), 20-23 June 2001, Cardiff, Wales, United Kingdom.
Oral presentation: Neil Donoghue, “Inhibition of HIV Infection by an Organo­arsenical of Low Toxicity.”

Society for Free Radical Research (Australasia): 8th Conference (theme: Oxidative Pathways in Health and Disease), 1-4 December 1999, University of Sydney, Darlington, Sydney, NSW, Australia.
Poster presentation: Neil Donoghue and Philip J. Hogg, “Development of a Specific Inhibitor of Secreted Redox-Active Proteins.”

Australian Society for Biochemistry and Molecular Biology (ASBMB): inaugural ComBio 1999, 27-30 September 1999, Conrad Jupiters Casino, Gold Coast, Qld, Australia.
Poster presentation: Neil Donoghue and Philip J. Hogg, “Development of a Specific Inhibitor of Secreted Redox-Active Proteins.”

University of New South Wales (UNSW), School of Chemistry (Inorganic Chemistry Department): Inter-Departmental Invited Speaker, 3 December 1996, Kensington, Sydney, NSW, Australia.
Oral presentation: Neil Donoghue, “Hydrogenated Triphenylphosphine (and other Chemical Curiosities based on Pentavalent Phosphorus).”

Royal Australian Chemical Institute (RACI) 75th Anniversary: 9th National Convention/RACI Organic Division: 13th National Conference, 6-11 December 1992, Monash University, Clayton, Melbourne, Victoria, Australia.
Poster presentation: Neil Donoghue and Michael J. Gallagher, “Reduction of Phosphonium Salts with Radical Anions.”

Other Conferences attended:

ARC Centre of Excellence in Bioinformatics (ACB) and Institute for Molecular Bioscience (IMB): Winter School in Mathematical and Computational Biology, 6-10 July 2009, University of Queensland, St. Lucia, Brisbane, Qld, Australia.

Australian Centre for Plant Functional Genomics (ACPFG): Joint Meeting, 25-26 June 2009, University of Adelaide (Waite campus), Urrbrae, Adelaide, SA, Australia.

Australian Society for Medical Research (ASMR): Medical Research Week State Scientific Meeting (NSW), 31 May 1999, Sebel Town House, Elizabeth Bay, Sydney, NSW, Australia.

Royal Australian Chemical Institute (RACI), NSW Branch, Organic Chemistry Group: 3 December 1996, University of Sydney, Darlington, Sydney, NSW, Australia.

Royal Australian Chemical Institute (RACI), NSW Branch, Natural Products Chemistry Group: 4 October 1996, University of Western Sydney, Nepean, Sydney, NSW, Australia.

Southern Highlands Conference on Heterocyclic Compounds, 1-3 September 1996, Milton Park, Bowral, NSW, Australia.

Royal Australian Chemical Institute (RACI), Organic Division: 14th National Conference, 3-8 July 1994, University of Wollongong, Wollongong, NSW, Australia.

Research Theses:

Neil Donoghue, “Aspects of Reductive Methods in Organo­phosphorus Chemistry” Ph.D. thesis, 1998, 199pp, School of Chemistry (Department of Organic Chemistry), University of New South Wales, Kensington, Sydney, NSW, Australia.

Neil Donoghue, “Diorgano­tin(IV) Xanthates and their Anti-Tumour Activity” Honours thesis, 1991, 53pp, Department of Physi­cal & Inorganic Chemistry, University of Adelaide, Adelaide, SA, Australia.