DEPARTMENT OF

Chemistry

 

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Donal Macartney

  • B.Sc., 1977, Ph.D., 1981, University of Victoria;
  • NSERC Postdoctoral Fellow, 1981-1983, Brookhaven National Laboratory;
  • NSERC University Research Fellow, 1983-1993.

 

Donal Macartney

Contact Information

Department of Chemistry,
Queen's University
Kingston, Ontario  K7L 3N6
 
Office: CHE506
Lab: CHE438N
 
Office Phone: 613-533-2617
Lab Phone: 613-533-2690
Fax: 613-533-6669

Research Interests

The research in my group involves the investigations of the supramolecular host-guest complexes of the family of macrocyclic host molecules, the cucurbit[n]urils (CB[n], n = 5-8, 10, and 14). These host molecules, which are cyclic oligomers of n glycoluril units bridged by 2n methylene groups, have a hydrophobic cavity with two polar constrictive portals rimmed with ureido carbonyl groups. The cucurbiturils have a particularly strong affinity for cationic guests, with binding constants up to 1017 M-1 in water, when both the hydrophobic effect and ion-dipole interactions can be maximized. We have research interests in a number of fundamental and applied areas of cucubit[n]uril supramolecular chemistry.

  • Effects of Complexation on Physical and Chemical Properties of Guests

The complexation of organic compounds and transition metal complexes by cucurbit[n]uril host molecules can have significant effects on the chemical, physical, and spectroscopic properties of the guest molecules in their ground and excited states.  These effects include changes in their pKa values, their stability, and their reactivity.  The properties of the host-guest complexes are investigated using UV-visible absorption and emission spectroscopy, NMR spectroscopy, ESI mass spectrometry, and cyclic voltammetry.

  • Selective Molecular Recognitions of Guests of Biological Interest

We are interested in the ability of cucurbit[7]uril to bind selectively to different quaternary ammonium cation groups, based size and hydrophobicity, located on guests of biochemical interest. We have shown, for example, that CB[7] exhibits excellent selectivity in the recognition of methylated lysines and arginines (important in histone post-translational modifications), with a 3500-fold selectivity for trimethyllysine over lysine.  This selectivity is larger than other artificial hosts and the native histone readers, despite a lack of aromatic groups and anionic charges, features found in the other hosts and native proteins.

  • Binding, Delivery, Reversal and Stabilization of Drug Molecules

The ability of the cucurbit[n]uril host molecules to selectively recognize and strongly bind a variety of guests of medicinal interest in aqueous solution makes them excellent vehicles for the delivery and release of drug molecules.  We are interested in the use of the host molecules for stabilization and controlled release of drugs, and their use in reversing the action of drugs (such as steroidal neuromuscular blocking agents) when their continued presence in the body could lead to side effects.

 

Recent Publications
 

95. Mona A. Gamal-Eldin and Donal H. Macartney, “Cucurbit[7]uril host-guest complexations of steroidal neuromuscular blocking agents in aqueous solution”, Canadian Journal of Chemistry, 2014, 92(3), 243-249.  http://dx.doi:10.1139/cjc-2013-0490

94. Julian Kwok and Donal H. Macartney, “Cucurbit[7]uril Complexation of Bis(isoquinolium)alkane Dications,” Supramolecular Chemistry, 2014, 26(3-4), 182-191.  http://dx.doi:10.1080/10610278.2013.842645

93. Donal H. Macartney, “Cucurbiturils in Drug Binding and Delivery”. In: Reedijk, J. (Ed.) Elsevier Reference Module in Chemistry, Molecular Sciences and Chemical Engineering2013, Waltham, MA: Elsevier. 1-Nov-2013 http://dx.doi:10.1016/B978-0-12-409547-2.05621-3

92. Donal H. Macartney, “Cucurbit[n]uril Type Hosts for the Reversal of Steroidal Neuromuscular Blocking Agents”, Future Medicinal Chemistry, 2013, 15(17), 2075-2089 (invited review article). http://dx.doi:10.1016/B978-0-12-409547-2.05621-3

91. Brendan C. MacGillivray and Donal H. Macartney, “Cucurbit[7]uril Host–Guest Complexes with Biguanidinium Cations in Aqueous Solution, European Journal of Organic Chemistry, 2013, 2573-2582.  http://dx.doi:10.1002/ejoc.201201655

90. Mona A. Gamal-Eldin and Donal H. Macartney, “Cucurbit[7]uril host–guest complexes and [2]pseudorotaxanes with N-methylpiperidinium, N-methylpyrrolidinium, and N-methylmorpholinium cations in aqueous solution”, Organic & Biomolecular Chemistry, 2013, 11, 1234-1241.  http://dx.doi:10.1039/c2ob27282b

89. Mona A. Gamal-Eldin and Donal H. Macartney, “Selective molecular recognition of methylated lysines and arginines by cucurbit[6]uril and cucurbit[7]uril in aqueous solution”,  Organic & Biomolecular Chemistry, 2013, 11, 488-495. http://dx.doi:10.1039/c2ob27007b

88. Brendan C. MacGillivray and Donal H. Macartney, “Complexations of the hydrophilic and hydrophobic moieties of benzethonium chloride by cucurbit[7]uril in aqueous solution,” Canadian Journal of Chemistry, 2012, 90, 851-857.  http://dx.doi:10.1139/v2012-078

87. Donal H. Macartney, “Encapsulation of Drug Molecules by Cucurbiturils: Effects on Their Chemical Properties in Aqueous Solution,” Israel Journal of Chemistry, 2011, 51 (5-6), 600-615.http://dx.doi:10.1002/ijch.201100040

86. Ian W. Wyman and Donal H. Macartney, “Cucurbit[7]uril Host-Guest Complexes of Local Anaesthetics in Aqueous Solution,” Organic & Biomolecular Chemistry, 2010, 8, 247-252.http://dx.doi:10.1039/b915694a

85. Ian W. Wyman and Donal H. Macartney, “Cucurbit[7]uril Host-Guest Complexes of Cholines and Phosphonium Analogues in Aqueous Solution,” Organic & Biomolecular Chemistry, 2010, 8, 253-260.  http://dx.doi:10.1039/b917610a

84. Daniel Foucher, Stephen Wylie, Donal H. Macartney, and Alan J. Lough, “3-Amino-1-methylpyrazin-1-ium Iodide,” Acta Crystallographica, 2010, E66, o60.  http://dx.doi:10.1107/S1600536809051253

Brendan C. MacGillivray and Donal H. Macartney, “Complexations of the hydrophilic and hydrophobic moieties of benzethonium chloride by cucurbi[7]uril in aqueous solution,” Can. J. Chem., 2012, in press.

Donal H. Macartney, “Encapsulation of Drug Molecules by Cucurbiturils: Effects on their Chemical Properties in Aqueous Solution,” Isr. J. Chem, 2011, 51, 600-614.

Ian W. Wyman and Donal H. Macartney, “Cucurbit[7]uril Host-Guest Complexes of Cholines and Phosphonium Analogues in Aqueous Solution,” Org. Biomol. Chem., 2010, 8, 253-260.

Ian W. Wyman and Donal H. Macartney, “Cucurbit[7]uril Host-Guest Complexes of Local Anaesthetics in Aqueous Solution”, Org. Biomol. Chem., 2010, 8, 247-252.

Daniel Foucher, Stephen Wylie, Donal H. Macartney and Alan J. Lough, “3-Amino-1-methylpyrazin-1-ium iodide”, Acta Cryst., 2010, E66, o60. 

Ian W. Wyman and Donal H. Macartney, “Host-Guest Complexes and Pseudorotaxanes of Cucurbit[7]uril with Acetylcholinesterase Inhibitors,” J. Org. Chem., 2009, 74, 8031-8038.

Ian W. Wyman and Donal H. Macartney, “Host-Guest and Rotaxane Complexes of Cucurbit[7]uril with Bis(pyridinium) Guests”, Org. Biomol. Chem., 2009, 7, 4045-4051.

Ruibing Wang, Ian W. Wyman, Shihao Wang and Donal H. Macartney, “Encapsulation of a -Carboline in Cucurbit[7]uril,  J. Incl. Phenom. Macrocyclic Chem., 2009, 64, 233-237.

Ruibing Wang, Brendan C. MacGillivray and Donal H. Macartney, “Stabilization of the base-off forms of vitamin B12 and coenzyme B12 by encapsulation of the -axial 5,6-dimethylbenzimidazole ligand with cucurbit[7]uril” Dalton Trans., 2009, 3584-3589.

Antony D. St-Jacques, Ian W. Wyman and Donal H. Macartney, “Encapsulation of charge-diffuse peralkylated onium cations in the cavity of cucurbit[7]uril, Chem. Commun., 2008, 4936-4938.

Ruibing Wang and Donal H. Macartney, “Cucurbit[7]uril Complexation of a Histidine H2-Receptor Antagonist Ranitidine”, Org. Biomol. Chem., 2008, 6, 1955-1960.

Ian W. Wyman and Donal H. Macartney, “Cucurbit[7]uril Complexes of Small Polar Organic Molecules in Aqueous Solution”, Org. Biomol. Chem., 2008, 6, 1796-1801.

Ruibing Wang and Donal H. Macartney, “Cucurbit[7]uril Stabilization of a Diphenylmethane Carbocation in Aqueous Solution”, Tetrahedron Lett., 2008, 49, 311-314.

Andrew J. Baer and Donal H. Macartney, “Orientational Isomers of Cyclodextrin Semirotaxanes and Rotaxanes with Organic and Transition Metal Complex Stoppers”, Supramol. Chem., 2007, 19, 537-546.

Tina J. Burchell, T. Stanley Cameron, Donal H. Macartney, Lawrence K. Thompson, and Manuel A. S. Aquino, “Kinetics and Magnetism of Phosphine Diadducts of Diruthenium(II,III) Tetraacetate”, Eur. J. Inorg. Chem., 2007, 4021-4027.

Ruibing Wang, Heiko Ihmels, Lina Yuan, and Donal H. Macartney, “Cucurbit[8]uril/Cucurbit[7]uril Controlled Fluorescence Off/On of Acridizinium and 9-Aminoacridizinium Cations in Aqueous Solutions”, Chem.–Eur. J., 2007, 13, 6468-6473.

Y. Sun, Nicole Ross, S.-B. Zhao, K. Huszarik, W.-L. Jia, R.-Y. Wang, Donal Macartney, and Suning Wang, “Enhancing Electron Accepting Ability of Triarylboron via -Conjugation with 2,2’-Bipy and Metal Chelation: 5,5’-Bis(BMes2)-2,2’-bipy and its Metal Complexes”, J. Am. Chem. Soc., 2007, 129, 7510-7511.

Lina Yuan and Donal H. Macartney, “Electron Exchange and Electron Transfer Reactions of Cucurbit[7]uril Host-Guest Complexes of Substituted Ferrocenes in Aqueous Solution”, J. Phys. Chem. B, 2007, 111, 6949-6954.

Lina Yuan, Ruibing Wang, and Donal H. Macartney, “Binding Modes of Cucurbit[6]uril and Cucurbit[7]uril with a Tetracationic Bis(viologen) Guest”, J. Org. Chem., 2007, 72, 4539-4542.

Lina Yuan, Ruibing Wang, and Donal H. Macartney, “Chiroptic Behaviour of Chiral Guests in an Achiral Cucurbit[7]uril Host”, Tetrahedron: Asymmetry, 2007, 18, 483-487.

J.A. Imonigie and D.H. Macartney, Effects of Inclusion of (Ferrocenylmethyl)trimethyammonium Complexes in Para-Sulfonated Calixarenes on the Kinetics of Their Electron Transfer Reactions, Inorganic Reaction Mechanisms, 6, 161-168 (2006).

R. Wang, L. Yuan, and D.H. Macartney, Inhibition ofC(2)-H/D exchange of a bis(imidazolium)dication upon complexation with cucurbit[7]uril, Chemical Communications, 2908-2910 (2006).

R. Wang, L. Yuan, and D.H.Macartney, The Stabilization of the (E)-1-ferrocenyl-2-(methyl-4-pyridiniumyl)ethylene Cation by Inclusion in Cucurbit[7]uril, Organometallics, 25, 1820-1823 (2006).

D.S.N. Hettiarachchi and D.H. Macartney, Cucurbit[7]uril Host-Guest Complexes with Bis(4,5-dihydro-1H-imidazoyl)arene Cations in Aqueous Solution, Canadian Journal of Chemistry, 84, 905-914 (2006).

R. Wang, L. Yuan, and D. H. Macartney, Cucurbit[7]uril Mediates the Stereoselective [4+4] Photodimerization of 2-Aminopyridine Hydrochloride in Aqueous Solution, Journal of Organic Chemistry, 71, 1237-1239 (2006).

R. Wang, L. Yuan, and D.H. Macartney, A green to blue fluorescence switch of protonated 2-aminoanthracene upon inclusion in cucurbit[7]uril, Chem. Commun., in press (2005).

V.X. Jin, D.H. Macartney, and E. Buncel, a- and b-Cyclodextrin [2]rotaxanes  with (diethylenetriamine)platinum(II) stoppers, Can. J. Chem., in press (2005).

V.X. Jin, D.H. Macartney, and E. Buncel, Assembly and Dissociation of a-Cyclodextrin [2]Pseudorotaxanes with a,w-Bis(N-(N,N”-dimethylethyene-diamine)alkane Threads, J. Incl. Phenom., 53, 197-203 (2005).

V.X. Jin, D.H. Macartney, and E. Buncel, Kinetic and Spectroscopic Studies on a- and b-Cyclodextrin Rotaxanes with (m-Bis(4’-pyridine)-a,w-diaminoalkanediimine)bis[pentacyanoferrate(II)] Stoppers, Can. J. Chem., 83, 185-191 (2005).

A.J. Baer and D.H. Macartney, Orientational Isomers of a-Cyclodextrin [2]Semi-Rotaxanes with Asymmetric Dicationic Threads, Org. Biomol. Chem., 3, 1448-1453 (2005).

J. Murray, D. Macartney, and G.R.J. Thatcher, Catalysis of NO Production by a Molybdoenzyme Model, Organic Letters, 3, 3635-3638 (2001).

Baer, Andrew J.; Macartney, Donal H.. a- and b-Cyclodextrin rotaxanes of m-bis(4-pyridyl)bis[pentacyanoferrate(II)] complexes. Inorganic Chemistry (2000), 39(7), 1410-1417.

Macartney, Donal H.; Roszak, Aleksander W.; Smith, K. Christopher. Effects of b-cyclodextrin inclusion on the kinetics of the oxidation of bisferrocenyl cations by bis(pyridine-2,6-dicarboxylato)cobaltate(III) in aqueous solution: crystal structure of dimethyldi(1-methylferrocene)ammonium bromide. Inorganica Chimica Acta (1999), 291(1-2), 365-371.

Smith, A. Catherine; Macartney, Donal H.. Kinetics of the Self-Assembly of a-Cyclodextrin[2]pseudorotaxanes with 1,12-Bis(4-(a-alkyl-a-methylmethanol)pyridinium)dodecane Dications in Aqueous Solution. Journal of Organic Chemistry (1998), 63(25), 9243-9251.

Lyon, Angela P.; Banton, Nicola J.; Macartney, Donal H.. Kinetics of the self-assembly of a-cyclodextrin [2]pseudorotaxanes with polymethylene threads bearing quaternary ammonium and phosphonium end groups. Canadian Journal of Chemistry (1998), 76(6), 843-850.

Clement, Omoshile; Macartney, Donal H.; Buncel, Erwin. Reactions of 1,10-phenanthroline complexes of Pt(II) with purines. Evidence for mono-coordinated 2,9-dimethyl-1,10-phenanthroline (dmphen) ligand in the complex between [Pt(dmphen)Cl2] and guanosine. Inorganica Chimica Acta (1997), 264(1-2), 117-124.

Lyon, Angela P.; Macartney, Donal H.. Kinetic and Spectroscopic Studies on a-Cyclodextrin Rotaxanes with Pentacyano(cyanopyridinium)ferrate(II) Stoppers. Inorganic Chemistry (1997), 36(4), 729-736.

Macartney, Donal H.. The self-assembly of a [2]pseudorotaxane of a-cyclodextrin by the slippage mechanism. Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1996), (12), 2775-2778.