Bruce E. Maryanoff

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Bruce Eliot Maryanoff (born February 26, 1947, in Philadelphia, Pennsylvania) is an American medicinal and organic chemist.

Contents

[edit] Education

Maryanoff received his B.S. in chemistry in 1969, and a Ph.D. in organic chemistry in 1972, both from Drexel University.[1] From 1972 to 1974 Maryanoff was a postdoctoral fellow in the Department of Chemistry at Princeton University. He joined McNeil Laboratories, Inc., a Johnson & Johnson subsidiary, in 1974 and advanced on the scientific ladder in various Johnson & Johnson pharmaceutical units to the highest scientific position in the company. He is now a Distinguished Research Fellow and Team Leader in Johnson & Johnson Pharmaceutical Research & Development, in Spring House, Pennsylvania.

[edit] Work

Maryanoff has been active in the fields of medicinal chemistry and organic chemistry. He invented TOPAMAX topiramate, a unique sugar sulfamate drug, which has been marketed worldwide for the treatment of epilepsy and migraine, and has exceeded $2 billion in annual sales. For this achievement, Johnson & Johnson honored him with its highest award, the Johnson Medal, in 1997. Maryanoff is an internationally renowned expert in drug design and drug discovery, especially in the application of protein structure-based drug design. His drug discovery work led to 23 compounds that entered preclinical development, 13 of which advanced into human clinical trials. He made seminal contributions to our understanding of the stereochemistry and mechanism of the Wittig reaction; adapted the cobalt-catalyzed alkyne trimerization to the synthesis of macrocycles; and devised novel peptides that undergo self-assembly to mimic native collagen structurally and functionally.

[edit] Publications and patents

Maryanoff is an author on 260 scientific publications, including 4 books (editor), 8 book chapters, and 22 other review articles. He is an inventor on more than 90 U.S. patents, issued (>60) or pending, and has presented over 150 invited lectures. He was an organizer and editor of a special issue of the Journal of Medicinal Chemistry to honor the memory of Dr. Paul Janssen (2005). He has served on numerous editorial advisory boards for scientific journals and review committees for grant proposals.

[edit] Awards and honors

  • Johnson & Johnson's Philip B. Hofmann Research Scientist Award, 1978
  • 23rd Achievement Award of the Philadelphia Section of the American Chemical Society (ACS), 1984
  • Johnson & Johnson's Philip B. Hofmann Research Scientist Award, 1987
  • Fellow, American Association for the Advancement of Science (AAAS), 1989
  • Distinguished Chemistry Alumni Award from Drexel University, 1994
  • Philadelphia Organic Chemists' Club (POCC) Award, 1995
  • Johnson Medal for Research and Development, 1997
  • Organic Syntheses Distinguished Lecture Award, Colorado State University, Department of Chemistry, 1998
  • Distinguished Alumni Achievement Award for Service to the Profession, Drexel University, 1999
  • American Chemical Society Heroes of Chemistry 2000 Award, 2000
  • Fellow, Royal Society of Chemistry (RSC), 2000
  • American Chemical Society Award in Industrial Chemistry, 2003
  • Drexel 100, 2003[2]
  • Wyeth Lecture Award, Temple University, School of Pharmacy, 2007

[edit] Selected publications

  • Maryanoff, B. E.; Reitz, A. B. “The Wittig Olefination Reaction and Modifications Involving Phosphoryl-Stabilized Carbanions. Stereochemistry, Mechanism, and Selected Synthetic Aspects.” Chem. Rev. 1989, 89, 863-927.
  • Sorgi, K. L.; Maryanoff, C. A.; McComsey, D. F.; Graden, D. W.; Maryanoff, B. E. “Asymmetric Induction in an Enammonium-Iminium Rearrangement. Mechanistic Insight via NMR, Deuterium Labeling, and Reaction Rate Studies. Application to the Stereoselective Synthesis of Pyrroloisoquinoline Antidepressants.” J. Am. Chem. Soc. 1990, 112, 3567-3579.
  • Maryanoff, B. E.; Qiu, X.; Padmanabhan, K. P.; Tulinsky, A.; Almond, H. R., Jr.; Andrade-Gordon, P.; Greco, M. N.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H.; Fusetani, N. “Molecular Basis for the Inhibition of Human alpha-Thrombin by the Macrocyclic Peptide Cyclotheonamide A.” Proc. Natl. Acad. Sci. USA 1993, 90, 8048-8052.
  • Maryanoff, B. E.; Greco, M. N.; Zhang, H.-C.; Andrade-Gordon, P.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H. “Macrocyclic Peptide Inhibitors of Serine Proteases. Convergent Total Synthesis of Cyclotheonamides A and B via a Late-Stage Primary Amine Intermediate. Study of Thrombin Inhibition under Diverse Conditions.” J. Am. Chem. Soc. 1995, 117, 1225–1239.
  • Maryanoff, B. E.; Costanzo, M. J.; Nortey, S. O.; Greco, M. N.; Shank, R. P.; Schupsky, J. J.; Ortegon, M. E.; Vaught, J. L. “Structure-Activity Studies on Anticonvulsant Sugar Sulfamates Related to Topiramate. Enhanced Potency with Cyclic Sulfate Derivatives.” J. Med. Chem. 1998, 41, 1315–1343.
  • Andrade-Gordon, P.; Maryanoff, B. E.; Derian, C. K.; Zhang, H.-C.; Addo, M. F.; Darrow, A. L.; Eckardt, A. J.; Hoekstra, W. J.; McComsey, D. F.; Oksenberg, D.; Reynolds, E. E.; Santulli, R. J.; Scarborough, R. M.; Smith, C. E.; White, K. B. “Design, Synthesis, and Biological Characterization of a Peptide-Mimetic Antagonist for a Tethered-Ligand Receptor.” Proc. Natl. Acad. Sci. USA 1999, 96, 12257–12262.
  • Mikami, K.; Shimizu, M.; Zhang, H.-C.; Maryanoff, B. E. “Acyclic Stereocontrol Between Remote Atom Centers via Intramolecular and Intermolecular Stereo-Communication.” Tetrahedron 2001, 57, 2917–2951.
  • Maryanoff, B. E. “Inhibitors of Serine Proteases as Potential Therapeutic Agents: The Road from Thrombin to Tryptase to Cathepsin G.” J. Med. Chem. 2004, 47, 769-787.
  • Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. “Cyclizations of N-Acyliminium Ions.” Chem. Rev. 2004, 104, 1431–1628.
  • Costanzo, M. J.; Almond, H. R., Jr.; Hecker, L. R.; Schott, M. R.; Yabut, S. C.; Zhang, H.-C.; Andrade-Gordon, P.; Corcoran, T. W.; Giardino, E. C.; Kauffman, J. A.; Lewis, J. M.; de Garavilla, L.; Haertlein, B. J.; Maryanoff, B. E. “In-Depth Study of Tripeptide Ketoheterocycles as Inhibitors of Thrombin. Effective Utilization of the S1’ Subsite and Its Implications to Structure-Based Drug Design.” J. Med. Chem. 2005, 48, 1984–2008.
  • de Garavilla, L.; Greco, M. N.; Sukumar, N.; Chen, Z.-W.; Pineda, A. O.; Mathews, F. S.; Di Cera, E.; Giardino, E. C.; Wells, G. I.; Haertlein, B. J.; Kauffman, J.; Corcoran, T. W.; Derian, C. K.; Eckardt, A. J.; Andrade-Gordon, P.; Damiano, B. P.; Maryanoff, B. E. “A Novel, Potent Dual Inhibitor of the Leukocyte Proteases Cathepsin G and Chymase: Molecular Mechanisms and Anti-inflammatory Activity In Vivo.” J. Biol. Chem. 2005, 280, 18001-18007.
  • Maryanoff, B. E.; McComsey, D. F.; Costanzo, M. J.; Hochman, C.; Smith-Swintosky, V.; shank, R. P. “Comparison of Sulfamate and Sulfamide Groups for the Inhibition of Carbonic Anhydrase-II by Using Topiramate as a Structural Platform.” J. Med. Chem. 2005, 48, 1941–1947.
  • Boñaga, L. V. R.; Zhang, H.-C.; Moretto, A. F.; Ye, H.; Gauthier, D. A.; Li, J.; Leo, G. C.; Maryanoff, B. E. “Synthesis of Macrocycles via Cobalt-Mediated [2 + 2 + 2] Cycloadditions.” J. Am. Chem. Soc. 2005, 127, 3473-3485.
  • Maryanoff, B. E. “Adventures in Drug Discovery: Potent Agents Based on Ligands for Cell-Surface Receptors.” Acc. Chem. Res. 2006, 39, 831-840.
  • Maryanoff, B. E. “Discovery of Potent Nonpeptide Vasopressin Receptor Antagonists.” Drug Discovery and Development, Vol. 1, M. S. Chorghade, Ed., Wiley, Hoboken, NJ, 2006, chapter 11, pp 313–337.
  • Greco, M. N.; Hawkins, M. J.; Powell, E. T.; Almond, H. R., Jr.; de Garavilla, L.; Hall, J.; Minor, L. K.; Wang, Y.; Corcoran, T. W.; Di Cera, E.; Cantwell, A. M.; Savvides, S. N.; Damiano, B. P.; Maryanoff, B. E. “Discovery of Potent, Orally Active, Nonpeptide Inhibitors of Human Mast Cell Chymase.” J. Med. Chem. 2007, 49, 1727–1730.
  • Cejas, M. A.; Kinney, W. A.; Chen, C.; Leo, G. C.; Tounge, B. A.; Vinter, J. G.; Joshi, P. P.; Maryanoff, B. E. “Collagen-Related Peptides: Self-Assembly of Short, Single Strands into a Functional Biomaterial of Micrometer Scale.” J. Am. Chem. Soc. 2007, 129, 2202–2203.
  • Zhang, H.-C.; Boñaga, L. V. R.; Ye, H.; Derian, C. K.; Damiano, B. P.; Maryanoff, B. E. “Novel Bis-(Indolyl)maleimide Pyridinophanes that are Potent, Selective Inhibitors of Glycogen Synthase Kinase-3.” Bioorg. Med. Chem. Lett. 2007, 17, 2863–2868.
  • Cejas, M. A.; Chen, C.; Kinney, Maryanoff, B. E. “Nanoparticles that Display Short Collagen-Related Peptides. Potent Stimulation of Human Platelet Aggregation by Triple Helical Motifs.” Bioconj. Chem. 2007, 18, 1025–1027.
  • Maryanoff, B. E.; Costanzo, M. J. “Inhibitors of Proteases and Amide Hydrolases that Employ an alpha-Ketoheterocycle as a Key Enabling Functionality.” Bioorg. Med. Chem. 2008, 16, 1562–1595.
  • Ye, H.; Chen, C.; Zhang, H.-C.; Haertlein, B. J.; Parry, T. J.; Damiano, B. P.; Maryanoff, B. E. “Carba-nucleosides as Potent Antagonists of the Adenosine 5’-Diphosphate (ADP) Purinergic Receptor (P2Y12) on Human Platelets.” ChemMedChem 2008, 3, 732–736.
  • Shank, R. P.; Maryanoff, B. E. “Molecular Pharmacodynamics, Clinical Therapeutics, and Pharmacokinetics of Topiramate.” CNS Neurosci. Ther. 2008, 14, 120–142.

[edit] References

  1. ^ NCCE Co-op Hall of Fame Class of 2002–2003. National Commission for Cooperative Education. Retrieved on 2008-02-26.
  2. ^ “The Drexel 100”, Drexel Blue & Gold 17 (1): 24–25, June 15, 2006, <http://www.drexel.edu/univrel/new/alumnimagazine/winter_2006.pdf>. Retrieved on 2008-01-12