Publications

Selected publications

Ducharme, J., Auclair*, K. Use of Bioconjugation with Cytochrome P450 Enzymes. BBA - Proteins and Proteomics, Accepted June 14, 2017 DOI: 10.1016/j.bbapap.2017.06.007.

Polic, V., Auclair*, K. Allosteric activation of cytochrome P450 3A4 via progesterone bioconjugation. Bioconj. Chem. 2017, 28, 885-889.

Ducharme, J., Auclair*, K. Enzymes beat chemists in the formation of unnatural bonds. ChemBioChem 2017, 18, 432-434.

Schiavini, P., Cheong, K. J., Moitessier*, N., Auclair*, K. Active site crowding of P450 3A4 as a strategy to alter its selectivity. ChemBioChem 2017, 18, 248-252.

Howieson, V. M., Tran, E., Hoegl, A., Fam, H. L., Fu, J., Sivonen, K. S., Li, X. M., Auclair*, K., Saliba*, K. J. Triazole substitution of the pantetheinase-sensitive amide bond stabilizes pantothenamides and improves their antiplasmodial potency. Antimicrob. Agents Chemother. 2016, 60, 7146-7152.

Hammerer, F., Chang, J., Duncan, D., Ruis, Angel C., Auclair*, K. Small molecule restores itaconate sensitivity in Salmonella enterica: a potential new approach to treat bacterial infections. ChemBioChem, 2016, 17, 1513-1517.

Guan, J., Hachey, M., Puri, L., Howieson, V., Saliba, K. J., Auclair*, K. A cross metathesis approach to novel pantothenamides derivatives. Beilstein J. Org. Chem. 2016, 12, 963-968.

Mariaule, G., De Cesco, S., Airaghi, F., Kurian, J., Schiavini, P., Rocheleau, S., Auclair, K., Mittermaier, A., Moitessier*, N. 3-Oxo-hexahydro-1H-isoindole-4-carboxylic acid as a drug chiral bicyclic scaffold and its application to the preparation of conformationally constrained covalent and non-covalent prolyl oligopeptidase inhibitors. J. Med Chem. 2016, 59, 4221-4234.

Schiavini, P., Pottel, J., Moitessier*, N., Auclair*, K. Metabolic instability of cyanothiazolidine-based prolyl oligopeptidase inhibitors: a Structural assignment challenge and potential medicinal chemistry implications. ChemMedChem 2015, 10, 1174-1183.

Freiburger, L., Auclair, K., Mittermaier*, A.K. Global ITC fitting methods in studies of protein allostery. Methods. 2015, 76, 149-161.

Freiburger, L., Miletti, T., Zhu, S., Baettig, O., Berghuis, A. M., Auclair, K., Mittermaier, A.K. Substrate-dependent switching of the allosteric binding mechanism of aminoglycoside (6') acetyltransferase-Ii. Nature Chem. Biol., doi: 10.1038/nchembio.1626.

Polic, V., Auclair, K. Controlling substrate specificity and product regio- and stereo-selectivities of P450 enzymes without mutagenesis. Bioorg. Med. Chem. 2014, doi: 10.1016/j.bmc.2014.06.034.

Hoegl, A., Darabi, H., Tran, E., Awuah, E., Kerdo, E., Saliba, K. J., Auclair, K. Stereochemical modification of geminal dialkyl substituents on pantothenamides alters antimicrobial activity. Bioorg. Med. Chem. Lett. 2014, 24, 3274-3277.

Awuah, E., Ma, E., Hoegl, A., Vong, K., Habib, E., Auclair, K. Exploring structural motifs necessary for substrate binding in the active site of Escherichia coli pantothenate kinase. Bioorg. Med. Chem. 2014, 22, 3083-3090.

Menard, A., Fabra, C., Huang, Y., Auclair, K. Type II ligands as chemical auxiliaries to favor enzymatic transformations by P450 2E1. ChemBioChem, 2012, 13, 2527-2536.

Larsen, A. T., Lai, T., Polic, V., Auclair, K. Dual use of a chemical auxiliary: molecularly imprinted polymers for the selective recovery of products from biocatalytic reaction mixtures. Green Chem. 2012, 14, 2206-2211.

Menard, A., Huang, Y., Karam, P., Cosa, G., Auclair, K. Site-Specific Fluorescent Labeling and Oriented Immobilization of a Triple Mutant of CYP3A4 via C64. Bioconjug. Chem. 2012, 23, 826-836.

Vong, K., Tam, I. S., Yan, X., Auclair, K. Inhibitors of aminoglycoside resistance activated in cells. ACS Chem. Biol. 2012, 7, 470-475.

Vong, K., Auclair, K. Understanding and overcoming aminoglycoside resistance caused by N-6'-acetyltransferase. Med. Chem. Commun. 2012, 3, 397-407.

Tewari, B. B., Beaulieu-Houle, G., Larsen, A., Auclair, K., Butler, I. S. An overview of molecular spectroscopic studies on theobromine and related alkaloids. Appl. Spectrosc. Rev. 2012, 47, 163-179.

Freiburger, L. A., Auclair, K., Mittermaier, A. K. Van't Hoff global analyses of variable temperature isothermal titration calorimetry data. Thermochimica Acta 2012, 527, 148-157.

Szychowski, J., Kondo, J., Zahr, O., Auclair, K., Westhof, E., Hanessian, S., Keillor, J. W. Inhibition of aminoglycosides-deactivating enzymes APH(3')-IIIa

Larsen, A. T., May, E. M., Auclair, K. Predictable stereo- and chemo-selective hydroxylations with P450 3A4. J. Am. Chem. Soc. 2011, 133, 7853-7858.

Akinnusi, T. O., Vong, K., Auclair, K. Geminal dialkyl derivatives of N-substituted pantothenamides: Synthesis and antibacterial activity. Bioorg. Med. Chem. 2011, 19, 2696-2706.

Freiburger, L. A., Baettig, O. M., Berghuis, A. M., Auclair, K., Mittermaier, A. K. Competing allosteric mechanisms modulate substrate binding in a dimeric enzyme, Nat. Struct. Mol. Biol. 2011, 18, 288-294.

Freiburger, L. A., Mittermaier, A. K., Auclair, K. Collecting variable-concentration isothermal titration calorimetry datasets in order to determine binding mechanisms. J. Vis. Exp. doi: 10.3791/2529 (http://www.jove.com/details.stp?id=2529).

Yan, X., Akinnusi, O., Larsen, A. T., Auclair, K. Synthesis of 4'-aminopantetheine and derivatization for bacterial studies. Org. Biomol. Chem. 2011,9, 1538-1546.

Freiburger, L. A., Auclair, K., Mittermaier, A. K. Elucidating Protein-Binding Mechanisms by Variable-c ITC. ChemBioChem, 2009, 10, 2871-2873.

Gao, F., Yan, X., Vong, K., Auclair, K. Synthesis of a phosphonate-linked aminoglycoside-CoA bisubstrate and use in mechanistic studies of an enzyme involved in aminoglycoside resistance. Chem. Eur. J. 2009, 15, 2064-2070. **invited to provide frontispiece for this issue.

Zhao, J., Auclair, K. The activity of human CYP2D6 in low water organic solvents. Biotech. Bioeng. 2009, 102, 1268-1272.

Gao, F., Yan, X., Zahr, O., Larsen, A., Vong, K., Auclair, K. Use of Sulfonamide-, Sulfoxide-, or Sulfone-containing Aminoglycoside-CoA Bisubstrates as Mechanistic Probes for Aminoglycoside N-6 -Acetyltransferase. Bioorg. Med. Chem. Lett. 2008, 18, 5518-5522. .

Kotakadi V, Jin Y, Hofseth AB, Ying L, Cui X, Volate S, Chumanevich A, Wood P, Price R, McNeal A, Singh UP, Singh N, Nagarkatti M, Nagarkatti P, Matesic LE, Auclair K, Wargovich MJ, Hofseth LJ. Ginkgo biloba extract EGb 761 has anti-inflammatory properties and ameliorates colitis in mice by driving effector T cell apoptosis.Carcinogenesis 2008, 29, 1799-1806.

Magalhães, M. L. B., Vetting,M. W., Gao, F., Freiburger, L., Auclair, K., Blanchard, J. S. Kinetic and Structural Analysis of Bisubstrate Inhibition of the Salmonella enterica. Biochemistry 2008, 47, 579-584.

Chefson, A., Auclair, K. CYP3A4 activity of in the presence of organic cosolvents, ionic liquids, or water-immiscible organic solvents. ChemBioChem. 2007, 8, 1189-1197.

Chefson, A., Zhao, J. Auclair, K. Sugar-mediated lyoprotection of human CYP3A4. J. Biotechnol. 2007, 130, 436-440.

Zhao, J., Ferras, J., Auclair, K. Activity of human P450 2D6 in biphasic solvent systems. Biotech. Bioeng. 2007, 98, 508-513.

Yan, X., Gao, F., Yotphan, S., Bakirtzian, P., Auclair, K. The use of aminoglycoside derivatives to study the mechanism of aminoglycoside 6'-N-acetyltransferase and the role of 6'-NH2 in antibacterial activity. Bioorg. Med. Chem. 2007, 15, 2944-2951.

Chefson, A., Auclair, K. Progress towards easier use of P450 enzymes. Mol. BioSyst. 2006, 2, 462-469. (featured in the cover page of the Journal and highlighted in the Chemical Biology Virtual Journal).

Gao, F., Yan, X., Shakya, T., Baettig, O. M., Ait-Mohand-Brunet, S., Berghuis, A. M., Wright, G. D., Auclair, K. Synthesis and structure-activity relationships of truncated bisubstrate inhibitors of aminoglycoside 6'-N-acetyltransferases. J. Med. Chem. 2006, 49, 5273-5281.

Chefson, A., Zhao, J., Auclair, K. Replacement of the natural cofactors by selected hydrogen peroxide donors or organic peroxides results in improved activity for CYP3A4 and CYP2D6. ChemBioChem 2006, 7, 916-919.

Gao, F., Yan, X., Matthias Baetig, O., Berghuis, A. M., Auclair, K. Regio- and chemo-selective N-6'-derivatization of aminoglycosides: Bisubstrate inhibitors and probes to study aminoglycoside 6'-N-acetyltransferases.Angew. Chem. Intl. Ed. Engl. 2005, 44, 2-6.

Gao, F., Auclair, K. Highly Efficient P(III) to P(V) Rearrangement. Phosphorus, Sulfur & Silicon 2004 accepted December 08, 2004.

Côté, C. S., Kor, C., Cohen, J., Auclair, K. Composition and biological activity of traditional and commercial kava extracts. Biochem. Biophys. Res. Comm. 2004 322, 147-152.

Gaudineau, C., Welbourn, S., Auclair, K. Inhibition of human P450 enzymes by multiple constituents of the Ginkgo biloba extract. Biochem. Biophys. Res. Comm. 2004 318(4), 1072-1078.

Gaudineau, C., Auclair, K. Inhibition of human P450 enzymes by nicotinic acid and nicotinamide Biochem. Biophys. Res. Comm. 2004 317(3), 950-956.

Auclair, K., Hu, Z., Little, D. M., Ortiz de Montellano, P. R., and Groves, J. T. Revisiting the Mechanism of P450 enzymes using the Radical Clocks Norcarane and Spiro[2,5]bicyclooctane, J. Am. Chem. Soc. 2002, 124(21), 6020-6027.

Auclair, K., Moenne-Loccoz, P., Ortiz de Montellano, P. R. Roles of the Proximal Thiolate Ligand of Cytochrome P450CAM, J. Am. Chem. Soc. 2001, 123 (21) 4877-4885.

Auclair, K. Book Review: Enzymes in Nonaqueous Solvents: Methods and Protocols, J. Chem. Soc., Perkin 1 2001, 17, 2104-2107.

Auclair, K. Book Review: Enzymes in Nonaqueous Solvents: Methods and Protocols, Nat. Prod. Rep. 2001, 5, 579-582.

Intellectual Property

Auclair, K., Gao, F. Yan, X. Amide-, sulphur-, or phosphoryl-tethered aminoglycoside-pantetheine derivatives as potent inhibitors of aminoglycoside resistance. Report of Invention filed at McGill on March 7, 2007; ref 07100.

U.S. patent 2006/0211634 A1 (application No. 11/359,274); entitled Inhibitors of aminoglycoside 6'-N-acetyltransferases, compositions and uses thereof; Auclair, K.; Gao, F.; Yan, X. / inventors, filed February 21, 2006.

Auclair, K., Gao, F. Yan, X. Inhibitors of aminoglycoside 6'-N-acetyltransferases, Report of Invention filed at McGill on February 21, 2006;

U.S. provisional patent application No. 60/653,979; entitled Aminoglycoside-CoA Conjugates Compositions and Uses Thereof; Auclair Karine, Gao Feng / inventors, filed February 18, 2005.

Auclair, K., Gao, F. Aminoglycoside-coenzyme A bisubstrates as inhibitors of aminoglycoside acetyltransferases, Report of Invention filed at McGill on December 1st, 2004; ref 05040.

Auclair, K., Marchessault, R. H. Fishing for Alzheimer's Polymorphic Amyloids, Report of Invention filed at McGill on September 27, 2004; ref 05037.

Browne, L. M., and Auclair, K. Techniques in Organic Chemistry, 12 Videotapes (two publications and one copyright in 1996): The copyright has been transferred to The Journal of Chemical Education: Software.

Media Coverage of our Work

Sun, K. Features story on antibiotic resistance, McGill Tribune Nov 2007.

Aiello, R. Herbal Medicines, McGill Daily, 15 Jan 2006.

McDonagh, P. The Green Chemistry Revolution, McGill News Summer 2005.

Bourdon, P. Professeur-chercheur a McGill, l'Alzheimer préoccupe Karine Auclair. Le Citadin Oct 2004.

 



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