George, Adrian - University of Sydney

研究领域

Using High Pressures in Synthesis Organometallic Chemistry Detection of steroid abuse in athletes New Developments in Chemistry Education Organometallic Chemistry: The project aim is to use the porphyrinogen and calixpyrrole structure as a ligand for metals engaged in catalysis reactions. By providing a cavity for the metal we intend to extend the lifetime of the catalyst and have the ability to modify the reactivity of the metal through a variety of interactions with the calixpyrrole host. Large radii lanthanoid metals, such as samarium, have been coordinated in the cavity. Syntheses of a range of these cavity materials has been developed. Detection of steroid use in sports: Dehydroepiandrosterone (DHEA), a naturally produced androgen, may be administered by athletes with the aim of increasing levels of the more active androgens such as testosterone (T) and dihydrotestosterone (DHT). The International Olympic Committee (IOC) prohibits DHEA administration in athletes, however its detection remains difficult due to an incomplete understanding of DHEA metabolism as well as inter-individual variations. In this study, Gas Chromatography-Mass Spectrometry (GC-MS) demonstrated that a single oral administration of DHEA (100 mg) to a subject altered the urinary steroid concentrations of androsterone (A) and etiocholanolone (Et). The ratio of the concentration of A to Et (A/Et) may provide a screening marker of DHEA administration. Values of A/Et less than 0.5, measured following DHEA administration, were compared to a reference distribution of A/Et values obtained from 858 urine samples. Only 3 of these had A/Et values less than 0.5. The urine samples collected after DHEA administration were also analysed by Gas Chromatography-Combustion-Isotope Ratio Mass Spectrometry (GC-C-IRMS) to determine the Carbon Isotope Ratio (CIR, d13C) of A and Et. This technique demonstrated that d13C A and d13C Et were reduced following the single administration of DHEA. The difference between d13C Et and d13C A increased from 1.6 ‰ at the time of administration to a maximum value of 5.2 ‰, which corresponded to a minimum A/Et value of 0.4. Multiple oral administrations of 100 mg DHEA, morning and night for seven days to a separate subject resulted in Et being 13C depleted in relation to the DHEA that was administered. Also, an unknown compound, detected in many of the GC-C-IRMS traces was shown to have d13C values similar to those of Et. This compound, identified as 3a-5-cyclo-5a-androstan-6b-ol-17-one, may prove to be an effective indicator of DHEA administration. Education in Chemistry: Detailed analysis, both qualitative and quantitative, of examination scripts from some first year chemistry units has been undertaken. When combined with qualitative data from students about their experiences and perceptions, a number of interesting questions can be addressed. Firstly, the question of the extent to which the outcomes from our current assessment system are a reflection of students’ understanding can be examined. Analysis of students’ approaches to examination questions provides information about both misconceptions held and overall motivations and goals (performance orientation versus mastery orientation). Such information can be used not only to improve teaching in areas of student difficulty, but can also inform curriculum design more generally, with the ultimate goal of promoting deeper student understanding of the material under study. Secondly, the analysis provides data that supports the common belief that organic chemistry is an area that some students simply ‘don’t get’. The existence of barriers to deeper understanding of organic chemistry has been proven, and the nature of these barriers examined. Such information has obvious implications for improving teaching and learning in this fundamental area of chemistry, although more work in this area is needed.

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Barrie, S., Bucat, R., Buntine, M., Burke da Silva, K., Crisp, G., George, A., Jamie, I., Kable, S., Lim, K., Pyke, S., Read, J., Sharma, M., Yeung, A. (2015). Development, evaluation and use of a student experience survey in undergraduate science laboratories: The advancing science by enhancing learning in the laboratory student laboratory learning experience survey. International Journal of Science Education, 37(11), 1795-1814. [More Information] Brooker, L., Cawley, A., Kazlauskas, R., Goebel, C., George, A. (2012). Carbon isotope ratio analysis of endogenous glucocorticoid urinary metabolites after cortisone acetate and adrenosterone administration for doping control. Drug Testing and Analysis, 4(12), 951-961. [More Information] Cawley, A., George, A. (2012). Complementary stable carbon isotope ratio and amount of substance measurements in sports anti-doping. Drug Testing and Analysis, 4(12), 897-911. [More Information] Schmid, S., Youl, D., George, A., Read, J. (2012). Effectiveness of a Short, Intense Bridging Course for Scaffolding Students Commencing University-level Study of Chemistry. International Journal of Science Education, 34(8), 1211-1234. [More Information] Cawley, A., Trout, G., Kazlauskas, R., George, A. (2011). The potential of urinary androstdiene markers to identify 4-androstenediol (4-ADIOL) administration in athletes. Forensic Science International, 208(1-3), 129-138. [More Information] Salouros, H., Collins, M., George, A., Davies, S. (2010). Isolation and identification of three by-products found in methylamphetamine synthesized by the Emde route. Journal of Forensic Sciences, 55(3), 605-615. [More Information] Cawley, A., Trout, G., Kazlauskas, R., Howe, C., George, A. (2009). Carbon isotope ratio (delta(13)C) values of urinary steroids for doping control in sport. Steroids, 74(3), 379-392. [More Information] Brooker, L., Parr, M., Cawley, A., Flenker, U., Howe, C., Kazlauskas, R., Schanzer, W., George, A. (2009). Development of criteria for the detection of adrenosterone administration by gas chromatography-mass spectrometry and gas chromatography-combustion-isotope ratio mass spectrometry for doping control. Drug Testing and Analysis, 1(11-12), 587-595. [More Information] O'Byrne, J., Britton, S., George, A., Franklin, S., Frey, A. (2009). Using academic predictors to identify first year science students at risk of failing. CAL-Laborate, 17(1), 15-25. Salouros, H., Collins, M., Tarrant, G., George, A. (2008). N-Cyanomethyl-N-Methyl-1-(3',4'-methylenedioxyphenyl)-2-propylamine: An MDMA Manufacturing By-Product. Journal of Forensic Sciences, 53(5), 1083-1091. [More Information] Cawley, A., Trout, G., Kazlauskas, R., George, A. (2008). The detection of androstenedione abuse in sport: A mass spectrometry strategy to identify the 4-hydroxyandrostenedione metabolite. Rapid Communications in Mass Spectrometry, 22(24), 4147-4157. [More Information] Buntine, M., Read, J., Barrie, S., Bucat, R., Crisp, G., George, A., Jamie, I., Kable, S. (2007). Advancing chemistry by enhancing learning in the laboratory (ACELL): A model for providing professional and personal development and facilitating improved student laboratory learning outcomes. Chemistry Education: Research and Practice, 8(2), 232-254. Frey, A., Gardiner, M., Stringer, D., Yates, B., George, A., Jensen, P., Turner, P. (2007). Buckling under strain: Relief of steric pressure occurs differently for samarium(III) porphyrinogen complexes of the pi-bound auxiliary ligands cyclopentadienyl and cyclooctatetraenediyl. Organometallics, 26(6), 1299-1302. Jamie, I., Read, J., Kable, S., Bucat, R., Buntine, M., Crisp, G., George, A., Barrie, S. (2007). From APCELL to ACELL and beyond - Expanding a multi-institution project from laboratory-based teaching and leaning. The Australian Journal of Education in Chemistry, 67, 7-13. Cawley, A., Kazlauskas, R., Trout, G., George, A. (2005). Determination of urinary steroid sulfate metabolites using ion paired extraction. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 825(1), 1-10. [More Information] Cawley, A., Kazlauskas, R., Trout, G., Rogerson, J., George, A. (2005). Isotopic fractionation of endogenous anabolic androgenic steroids and its relationship to doping control in sports. Journal of Chromatographic Science, 43(1), 32-38. Cawley, A., Hine, E., Trout, G., George, A., Kazlauskas, R. (2004). Searching For New Markers Of Endogenous Steroid Administration In Athletes: 'Looking Outside The Metabolic Box'. Forensic Science International, 143(2-3), 103-114. [More Information] Munk, V., George, A. (2003). Small group learning in first year chemistry: Does it work? The Australian Journal of Education in Chemistry, 62, 9-12. George, A., Kim,, J., Ohga,, Y., Asano,, T., Weinberg, N. (2001). Pressure and viscosity effects on thermal geometrical isomerization of oxacarbocyanine cations. Bulletin of the Chemical Society of Japan, 74, 103-111.