Transition metal mediated synthetic organic chemistry
Chemical education
Bachelor of Science (1975) Illinois Institute of Technology, graduation with honors.
Master of Science(1982) Loyola University of Chicago
Thesis research under Prof. James W. Wilt : Synthesis and Chemistry of 8-methylene-exo-3,3-diphenyltricyclo [3.2.1.0.2,4] octane.
Klein, L.L., Tufano, M.D. "Synthesis of Substituted Isatins" Tetrahedron Letters, 54(8), 1008 (2013)
DeGoey DA1, Randolph JT, Liu D, Pratt J, Hutchins C, Donner P, Krueger AC, Matulenko M, Patel S, Motter CE, Nelson L, Keddy R,Tufano M, Caspi DD, Krishnan P, Mistry N, Koev G, Reisch TJ, Mondal R, Pilot-Matias T, Gao Y, Beno DW, Maring CJ, Molla A, Dumas E, Campbell A, Williams L, Collins C, Wagner R, Kati WM. “ Discovery of ABT-267, a pan-genotypic inhibitor of HCV NS5A “J Med Chem., 57(5), 2047 (2014).
Clark, R.F.; Wang, S.; Ma, Z.; Weitzberg, M.; Motter, C.; Tufano, M.D.; Wagner, R.; Gu, Y.G.; Dandliker, P.J.; Lerner, C.G.; Chovan, L.E.; Cai, Y.; Black-Schaefer, C.L.; Lynch, L.; Kalvin, D.; Nilius, A.M.; Pratt, S.D,; Soni, N.; Zhang, T.; Zhang, X.; Beutel, B.. Novel inhibitors of bacterial protein synthesis: structure-activity relationships for 1,8- naphthyridine derivatives incorporating position 3 and 4 variants. Bioorganic and Medicinal Chemistry Letters, 2004, 14(12), 3299-302.
Clark,R.F.; Ma, Z.; Wang, S.; Griesgraber, G.; Tufano, M.D.; Yong, H.; Li, L.; Zhang, X.; Nilius, A.M.; Chu, D.T.; Or, Y.S.. Synthesis and antibacterial activity of novel 6-O substituted erythromycin A derivatives. Bioorganic and Medicinal Chemistry Letters, 2000, 10(8), 815-9
Hajduk, P.J.; Dinges, J.; Schkeryantz, J.M.; Kaminski, M.; Tufano, M.D.; Augeri, D.J.; Petros, A.; Nienaber, V.; Zhong, P.; Hammond, R.; Coen, M.; Beutel,B.; Katz, L.; Fesik, S.W.. Novel inhibitors of Erm methyltransferases from NMR and parallel synthesis. Journal of Medicinal Chemistry, 1999, 42(19), 3852-9.
Li.Q.; Wang, W.; Berst, K.B.; Claiborne, A.; Hasvold, L.; Raye, K.; Tufano, M.D.; Nilius, A,; Shen, L.L.; Flamm, R.; Alder, J.; Marsh, K.; Crowell, D.; Chu, D.T.; Plattner, J.J.. Synthesis and structure activity relationships of 2-pyridones: II 8-(Fluoro-substituted pyrrolidinyl)-2-pyridones as antibacterial agents. Biooraganic and Medicinal Chemistry Letters, 1998, 8(15), 1953-8
Cooper, C.S.; Tufano, M.D.; Donner, P.K.; Chu, D.T.W. The synthesis and in vitro antibacterial activity of conformationally restricted quinolone antibacterial agents. Bioorganic & Medicinal Chemistry, 1996, 4(8), 1307-15.
Li,Q.; Chu, D.T.W.; Claiborne, A.; Cooper, C.S.; Lee, C.M.; Raye, K.; Berst, K.B.; Donner, P.; Wang, W.; Hasvold, L.; Fung, A.; Ma, Z.; Tufano, M.; Flamm, R.; Shen, L.L.; Baronowski, J.; Nilius, A.; Alder, J.; Meulbroek, J.; Marsh, K.; Crowell,D.; Hui, Y.; Seif, L.; Melcher, L.M.; Henry, R. Spanton, S.; Faghih, R.; Klein, L.L.; Tanaka, K.S.; Plattner, J.J. Synthesis and structure-activity relationships of 2-pyridones: A novel series of potent DNA Gyrase inhibitors as antibacterial agents. J. Med. Chem., 1996, 39(16), 3070-88.
Elliot, R.L.; Kopecka,H.L.; Tufano, M.D.; Shue, Y.K.; Guare, A.J.; Lin, C.W.; Bianchi, B.R.; Miller, T.R.; Witte, D.G. Novel Asp32-replacement tetrapeptide analogs as potent and selective CCK-A agonists. J. Med. Chem., 1994, 37(11), 1562-8.
Shue, Y.K.; Tufano, M.D.; Carrera, G.M.; Kopecka, H.; Kuyper, S.L.; Holladay, M.W.; Lin, C.W.; Witte, D.G.; Miller, T.R. Double bond isosteres of the peptide bond: synthesis and biological activity of cholecystokinin (CCK) C-terminal hexapeptide analogs. Bioorg. Med. Chem., 1993, 1(3), 161-71.
Nadzan, A.M.; Garvey, D.S.; Holladay, M.W.; Shiosaki, K.; Tufano, M.D.; Shue, Y.K.; Chung, J.Y.L.; May, P.D.; May, C.S. Design of cholecystokinin analogs with high affinity and selectivity for brain CCK receptors. Pept.: Chem. Biol. Proc.Am.Pept.Symp. 12th(1992) meeting date 1991, 100-2. Editors: Smith, J.A.; Rivier, J.E. Publisher: ESCOM, Leiden, Neth.
Holladay, M.W.; Bennett, M.J.; Tufano, M.D.; Lin, C.W.; Witte, D.G.; Miller, T.R.; Bianchi, B.R.; Nadzan, A.M. CCK heptapeptide analogs: Effect of conformational restrictions and standard modifications on selectivity and activity at CCK-A and CCK-B receptors. Pept.: Cem. Biol., Proc. Am. Pept. Symp., 12th (1992), meeting date 1991, 443-5. Editors: Smith, J.A.; Rivier, J.E. Publisher: ESCOM, Leiden, Neth.
Holladay, M.W.; Bennett, M.J.; Tufano, M.D.; Lin, C.W.; Asin, K.E.; Witte, D.G.; Miller, T.R.; Bianchi, B.R. Nikkel, A.L. Synthesis and biological activity of CCK heptapeptide analogs. Effects of conformational constraints and standard modifications on receptor subtype selectivity, functional activity in vitro, and appetite suppression in vivo. J. Med. Chem. 1992, 35(16), 2919-28.
Britton, D.R.; Curzon, P.; Yahiro, L.; Buckley, M. Tufano, M.; Nadzan, A. Evaluation of a Stable CCK Agonist (A68552) in Conditioned Avoidance Responding in Mice, Rats and Primates: Comparison With Typical and Atypical Antipsychotics. Pharmacology Biochemistry and Behavior,1992, 43,369-76.
Shiosaki, K; Lin, C.W.; Kopecka, H.; Tufano, M.D.; Bianchi, B.R.; Miller, T.R.; Witte, D.G.; Nadzan, A.M. Boc-CCK-4 derivatives containing side chain ureas as potent and selective CCK-4 receptor agonists. J. Med. Chem., 1991, 34(9), 2837-42.
Shue, Y.K.; Carrera, G.M.; Tufano, M.D.; Nadzan, A.M.; Novel Methodology for the synthesis of trans-alkene dipeptide isosteres. J. Org. Chem., 1991, 56(6), 2107-11.
Peeran, M.; Wilt, J.W.; Tufano, M.D.; Subramanian, R. Crumrine, D.S. Effect of a proximate phenyl ring on additions to bridged ketones. J. Org. Chem., 1990, 55(13), 4225-6.
Shue, Y.K.; Tufano, M.D.; Nadzan, A.M. Amide Bond surrogates: a novel synthesis of the Leu-Asp trans carbon-carbon double bond isostere of CCK-4. Tet.Lett., 1988, 29(33), 4041-4.
Nadzan, A.M.; Shue, Y.K.; Carrera, G.M.; Kerwin, J.F.; Kopecka, H.; Tufano, M.D.; Lin, C.W.Peptide bond modifications. Trans carbon-carbon double bond analogs of cholecystokinin. Pept. Chem., 1988, 549-52.
Lin, C.W.; Bianchi, B.R.; Grant, D.; Miller, T.; Danaher, E.A.; Tufano, M.D.; Kopecka, H.; Nadzan, A.M. Cholecystokinin receptors: relationships among phosphoinositide breakdown, amylase release and receptor affinity in pancreas. J. Pharmacol. Exp. Ther., 1986, 236(3), 729-34.
Wilt, J.W.; Tufano, M.D. 8-Methylene-exo-3,3-diphenyltricyclo [3.2.1.0.2,4] octane, a probe for addition reaction mechanism. J. Org. Chem., 1985, 50(14), 2600-1.
Presentations
Wagner, R.; Maring, C.; Donner, P.; Randolph, J.; Krueger, A.; Kati, W.; Koev, G.; Liu, Y.; Beno, D.; Shen, J.; Gao, Y.; Lau, Y.Y.; Fischer, J.; Vaidyanathan, S.; Beyer, J.; Lim, B.H.; Mondal, R.; Rockway, T.; Pratt, J.; Liu, D.; Tufano, M.; Molla, A.. Preclinical characterization of ABT-072: A novel non-nucleoside HCV polymerase inhibitor. 44th Annual Meeting of the European Associaation for the Study of the Liver, Copenhagen, Denmark, April 2009
Soni, N.B.; Nilius, A.M.; Keyes, R.F.; Tufano, M.; Wagner, R.; Merta, P.J.; Beutel, B.A.. Identification of novel antibacterial compounds which inhibit dihydrofolate reductase. 43rd Annual Interscience Conference on Antimicrobial Agents and Chemotherapy, Chicago, IL., September 2003.
Phan, L.T.; Or, Y.S.; Spina, K.P.; Chen, Y.; Tufano, M.; Chu, D.T.W.; Nilius, A.M.; Bui, M.H.; Plattner, J.J.. Tricyclic ketolides: Mono-substitution on the imine ring. Synthesis and in-vitro antibacterial activity. 37th Annual Interscience Conference on Antimicrobial Agents and Chemotherapy, Toronto, Ontario, Canada, September 1997.
Or. Y.S.; Spina, K.; Tufano, M.; Plattner, J.; Chu, D.; Tricyclic Macrolides. 212th American Chemical Society National Meeting, Orlando, Florida, August, 1996.
Experience
Northeastern Illinois University Chicago, Ill. 2012 - 2019
General chemistry laboratory instructor, department of Chemistry
Oversee teaching laboratory operation.
Responsible for approximately fifty students.
Provide guidance and evaluation.
Chicago Archdiocese Chicago, Ill. 2011 - 2012
Substitute teacher
Primary school level (K-8) duties.
Implement lesson plan as per instructions of primary teacher.
Abbott Laboratories Abbott Park, Ill. 1982 - 2011
Senior research chemist. Therapeutic area, antiviral 2002 - 2011
Supervised the work of an associate chemist.
Provided timely support for project virology by participating in the synthesis of an HCV benchmark protease inhibitor.
Applied focused SAR to quickly demonstrate the inability to dissociate cardiovascular activity from a screening hit having notable antiviral (HCV protease) activity.
Provided synthetic support to early lead development of a putative NS5A HCV inhibitor.
Provided synthetic support to thiadiazene series HCV polymerase inhibitor program.
Synthesized substituted benzthiophene and benzofuran HCV polymerase inhibitors.
Participated in a multidisciplinary team approach advancing a micro molar polymerase inhibitor screening hit to a safe and efficacious clinical candidate ( ABT 333 ) and back up ( ABT-072 ).
Provided synthetic support to HCV NS5A inhibitor program culminating in the discovery of a proprietary series of safe and efficacious inhibitors.
Prepared proprietary, novel early lead imidazothiazole HCV polymerase inhibitors.
Departmental safety officer.
Senior research chemist. Therapeutic area, anti-infective 1990 – 2002
Utilized heterocyclic chemistry to create novel antibacterial and anti-tumor agents.
Synthesized conformationally constrained quinolone class antibacterial agents.
Contributed to the development of a synthetic route to potent, broad-spectrum 2-pyridone class of antibacterial agent.
Synthesized novel 6-O substituted Erythromycin A analogs for SAR study of in vitro antibacterial activity.
Contributed to the medicinal chemistry team advancing a 6-O substituted ketolide ( ABT-773 )to clinical candidate status.
Participated in SAR study of tricyclic ketolides derived from 6-O-Me Erythromycin A (Clarithromycin) to identify analogs having broad-spectrum efficacy as well as activity against resistant bacterial strains.
As a member of a small multidisciplinary team, applied the concept of SAR by NMR to identify and optimize a novel inhibitor of Erm methyltransferase.
Provided synthetic support to a major program for the purpose of identifying a novel, proprietary small molecule bacterial ribosome inhibitor.
Departmental safety officer.
Research chemist. Therapeutic area, neuroscience. 1982 - 1990
Peptide chemistry. Synthesized peptidomimetics of a truncated form of the putative neuropeptide cholecystokinin (CCK).
Developed synthesis and purification protocol (gel filtration /HPLC) of short chain cyclic peptides including cyclic disulfides.
Conducted standard peptide SAR work.
Synthesized non-natural amino acids, dehydroamino acids.
Experienced with solution phase coupling protocol.
Departmental safety officer.
Universal Oil Products Des Plaines, Ill. 1975 - 1982
Research chemist, chemical and biochemical research group 1977 - 1982
Emphasis on lubricating oil, gasoline and rubber additives.
Experienced in high pressure/autoclave operations.
Experienced with reductive alkylation fixed bed catalyst development and pilot plant operation.
Analytical service group technician 1975 - 1977
Supported pilot plant and research laboratory operations.
Utilized gas chromatographic methods for analyzing solid, liquid and gaseous samples.
Patents
WO 2010144646 A2 Heterocyclic compounds as antiviral agents and their preparation and use in the treatment of hepatitis C virus infection. DeGoey, D.A.; Kati, W.M.; Hutchins, C.W.; Donner, P.L.; Krueger, A.C.; Randolph, J.T.; Motter, C.E.; Nelson,L.T.; Patel, S.V.; Matulenko, M.A.; Keddy, R.G.; Jinkerson, T.K.; Soltwedel, T.N.; Hutchinson, D.K.; Flentge, C.A.; Wagner, R.; Maring, C.J.; Tufano, M.D.; et.al..
WO 2010111436 A2 Preparation of pyrimidinyl 1-substituted naphthalenylmethanesulfonamide derivatives and analogues as inhibitors of hepatitis C virus. Betebenner, D.A,; Pratt, J.K.; Degoey, D.A.; Donner, P.L., Flentge, C.A.; Hutchinson, D.K.; Kati, W.M.; Krueger, A.C.; Longenecker, K.L.; Maring, C.J.; Randolph, J.T.; Rockway, T.W.; Tufano, M.D.; Wagner, R..
US 7763731 B2 Preparation of 1,6 and 1,8-naphthyridines as antiviral compounds for treatment of HCV infections. Rockway, T.R.; Betebenner, D.A.; Krueger, A.C.; Iwasaki, N.; Cooper, C.S.; Andesrson, D.D.; Kempf, D.J.; Madigan, D.L.; Motter, C.E.; Shanley, J.P.; Tufano, M.D.; et.al..
WO 200939127 A1 Uracil or thymine derivative for treating hepatitis C and their peparation, Wagner, R.; Tufano, M.D.; et.al..
WO 200781517 A2 Preparation of fused bicyclic heterocycles, particularly substituted 4-aminophenylpyrido(2,3-d)pyrimidines, as anti-viral compounds for treatment of HCV infections. Betebenner, D.A.; Degoey,D.A.; Maring, C.J.; Krueger, A.C.; Iwasaki, N.; Rockway, T.W.; Cooper, C.S.; Andersom, D.D.; Donner, P.L.; Green, B.E.; Kempf, D.J.; Liu, D.; McDaniel, K.F.; Madigan, D.L.; Motter, C.E.; Pratt, J.K.; Shanley, J.P.; Tufano, M.D.; et.al..
WO 200776034 A2 Preparation of naphthyridines and pyridopyrimidines as antiviral compounds for treatment of HCV infections. Betebenner, D.A.; Degoey,D.A.; Maring, C.J.; Krueger, A.C.; Iwasaki, N.; Rockway, T.W.; Cooper, C.S.; Andersom, D.D.; Donner, P.L.; Green, B.E.; Kempf, D.J.; Liu, D.; McDaniel, K.F.; Madigan, D.L.; Motter, C.E.; Pratt, J.K.; Shanley, J.P.; Tufano, M.D.; et.al..
US 6,274,715 B Preparation of tricyclic erythromycins as bactericides. Or, Y.S.; Phan, L.T.; Chu, D.T.; Spina, K.P.; Hallas, R.; Elliot, R.L.; Tufano, M.D.
US 5,340,802 A Preparation of peptide analog cholecystokinin type B receptor agonists. Shiosaki, K; Nadzan, A.M.; Garvey,D.S.; Shue,Y.K.; Brodie,M.S.; Holladay, M.W.; Chung,J.Y.L.; Tufano,M.D.; May,P.D.
EP 405506A1-(910102) Preparation of tetrapeptide type-B CCK receptor ligands. Chung,J. Y.L.,; Tufano, M.D.; May, P.D.; Shisaki, K.; Nadzan, A.M.; Garvey, D.S.; Shue, Y.K.; Brodie, M.S.; Holladay, M.W.
US 4,318,820 (1982) Chiral supports for resolution of racemates. Malloy, T.P.; Tufano, M.D.
US 4,318,819 (1982) Chiral supports for resolution of racemates. Malloy,T.P.; Tufano, M.D.
US 4,313,002 (1982) p-Aminodiphenylamines. Symon,T.; Kurek, P.R.; Tufano, M.D.
US 4,287,372 (1981) Nitro substituted diphenyl ethers. Tufano, M.D.
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