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April 2012 NUCLEUS Web DED UN 18 O 98 F http://www.nesacs.org N Y O T R E I T H C E N O A E S S S L T A E A C R C I th N S M A 90 Anniversary Issue of The NUCLEUS S E E H C C TI N April 2012 Vol. XC, No. 8 O CA N • AMERI Monthly Meeting Summer Scholar Report 2012 Esselen Award Meeting at Harvard Regioselective Hydroformylation of Nosyl-protected Esselen Award to Professor Bruce Ganem Homoallylic Sulfonamides Ka H. Cheng and Kian L. Tan, Boston College HepatoChem April Historical Events An Interview of HepatoChem President, Marc Bazin in Chemistry By Leopold May, Catholic University of America Synthetic Liver Metabolites An interview with HepatoChem President, Marc Bazin By Michael P. Filosa HepatoChem (http:// (Fig 3). www.hepatochem.com/) HepatoChem has also partnered with Princeton-based is a company co-found - Novatia, http://www.enovatia.com/, a capillary NMR con- ed in 2008 by Marc tract laboratory, to do structure elucidation of metabolites Bazin, formerly of with small amounts of material (0.1-0.5 mg). Pfizer, and Professor Although only a four-person company at this stage, John T. Groves, holder HepatoChem already has numerous clients ranging from of the Hugh Stott Taylor start-ups to big Pharma. “Our clients are very satisfied with Chair of Chemistry at the quality and speed of our service.” Dr. Bazin stated that Princeton University. the business in liver metabolites is $100 million per year HepatoChem was started and their business is expected to grow rapidly for a number in the Groves lab at of years. “This is very exciting to see our company growing Princeton, but in August in this economy.” u 2011 moved to the Biotech InnoVenture Center in Beverly, MA. President Marc Bazin (r) and Project My interest in Hepa- manager Ryan Buzdygon photographed toChem was piqued by in HepatoChem’s Beverly laboratory. Business Development Manager Shelly Amster at a recent NESACS Monthly Meeting. A subsequent interview was arranged with HepatoChem President, Marc Bazin, at their Beverly facility. HepatoChem uses technology based on many years of metalloporphyrin research conducted at Princeton in the Groves laboratory. A variety of metalloporphyrins (Fig. 1) Fig. 1: A Synthetic Metalloporphyrin are used to simulate liver metabolism and oxidatively con- vert drug candidates in vitro to metabolites in milligram to gram quantities. This is in stark contrast to the nanogram quantities available by in vitro or in vivo biological methods. Easy access to large quantities of metabolites allows struc- ture determination and additional evaluation and testing, which would not be possible without the larger quantities available from HepatoChem’s biomimetic methods. “The technology we developed at HepatoChem can produce not Fig. 2. Graphical illustration of metabolites formed by the only metabolites but also new analogues of lead candidates oxidation of aminopyrine with HepatoChem’s technology. that could have better biological properties than the original drug. This positions it as an important tool for drug discov- ery.” Initial screening is done in 96-well plates loaded with the test molecule. A series of test reactions are then con- ducted in which the metalloporphyrin, the oxidant, and the solvent are varied. These experiments are then analyzed by Fig. 3: Metabolites formed by biomimetic oxidation of LC-MSMS to identify a profile of metabolites and allows Tolbutamide. rapid selection of conditions to produce the targeted metabolite. (Fig 2) A second round of experiments allows optimization and larger scale production of any or all of the metabolites generated in the screen. Your one-stop source to career-related links Examples of reactions which can be achieved with met- in the Chemical Sciences alloporphyrin oxidation are hydroxylation, imine and enam- ine formation, halogenation, carbene insertion, amine WWW.NESACS.ORG/CAREERS formation and dealkylation. Tolbutamide is an example which illustrates aliphatic hydroxylation and dealkylation 2 The Nucleus April 2012 The Northeastern Section of the American Chemical Society, Inc. Contents NESACS Office Anna Singer, 12 Corcoran Road, Burlington, MA 01803 Synthetic Liver Metabolites 2 (Voice or FAX) 781-272-1966. ______________________________ e-mail: secretary(at)nesacs.org An Interview of HepatoChem President Marc Bazin http://www.NESACS.org By Michael P. Filosa Officers 2012 Chair April Historical Events in Chemistry 4 Ruth Tanner ________________________ Olney Hall 415B By Leopold May, Catholic University of America Lowell, MA 01854 University of Mass Lowell Ruth_Tanner(at)uml.edu Monthly Meeting _______________________________________5 978-934-3662 Esselen Award Meeting at Harvard University Chair-Elect Esselen Award to Professor Bruce Ganem, Cornell University Liming Shao Sunovion Pharmaceuticals Inc. Address: Lost (Sometimes) in Translation: Advancing Chemical Discoveries 84 Waterford Drive Beyond the Laboratory Marlborough, MA 01752 lshao(at)fas.harvard.edu Immediate Past Chair Announcements ______________________________________6,7 Patrick M. Gordon New England Association of Chemistry Teachers (NEACT), Central 1 Brae Circle Division Meeting. Lyman C. Newell Grants for the 73rd NEACT Woburn, MA 01801 Patrick.gordon65(at)gmail.com Summer Conference. NSYCC Northeast Student Research Conference, Secretary: NESACS Evening at a Red Sox Game Michael Singer Sigma-Aldrich 3 Strathmore Rd, Natick, MA 01360 NESACS Candidates for 2012 Election _____________________7 774-290-1391, michael.singer(at)sial.com Treasurer: Summer Scholar Report 8 James Piper _________________________________ 19 Mill Rd, Harvard, MA 01451 Regioselective Hydroformylation of Nosyl-protected Homoallylic Sulfonamide. 978-456-3155, piper28(at)attglobal.net Ka H. Cheng and Kian L. Tan, Department of Chemistry, Boston College. Auditor: Anthony Rosner Announcement 11 Archivist _______________________________________ Tim Frigo Chemistry of Food Science Café at Think Tank Bistrotheque, Trustees: One Kendall Square, Cambridge, MA Peter C. Meltzer, Esther A. H. Hopkins, Michael E. Strem Directors-at-Large Cover: 2012 Esselen Award winner Professor Bruce Ganem. (Photo courtesy David Harris, Stephen Lantos, James Phillips, of Professor Ganem). Ralph Scannell, Alfred Viola, John Burke Councilors Alternate Councilors Deadlines: Summer 2012 Issue: June 15, 2012 Term Ends 12/31/2012 Amy E. Tapper Jerry P. Jasinski September 2012 Issue: July 15, 2012 Catherine E. Costello Gary R. Weisman Patricia A. Mabrouk Norton P. Peet Dorothy J. Phillips Edward J. Brush Ruth Tanner Michael Hurrey th Term Ends 12/31/2013 90 Anniversary Issue of The NUCLEUS Thomas R. Gilbert Alfred Viola The Nucleus is published monthly, except June and August, by the Northeastern Section of the American Michael Singer Sophia R. Su Chemical Society, Inc. Forms close for advertising on the 1st of the month of the preceding issue. Text Robert Lichter Kenneth C. Mattes must be received by the editor six weeks before the date of issue. Mary Shultz Tim Frigo Leland L. Johnson, Jr. Raj (SB) Rajur Editor: Michael P. Filosa, Ph.D., ZINK Imaging, Inc., 16 Crosby Drive, Building 4G, Term Ends 12/31/2014 Bedford, MA 01730 Email: Michael.filosa(at)zink.com; Tel: 508-843-9070 Katherine Lee Michaeline Chen Associate Editors: Myron S. Simon, 20 Somerset Rd., W. Newton, MA 02465, Tel: 617-332-5273, Michael P. Filosa C. Jaworek-Lopes Sheila E Rodman, Konarka Technologies, Inc., 116 John St. Suite 12, Lowell, Doris Lewis Jennifer Larese MA 01852 Email: srodman(at)konarka.com tel 978-569-1414, Morton Z. Hoffman Lawrence Scott Mindy Levine, 516-697-9688, mindy.levine(at)gmail.com Patrick Gordon Marietta Schwartz Mary Burgess Andrew Scholte Board of Publications: Mary Mahaney (Chair), Mindy Levine, Vivian K. Walworth Business Manager: Karen Piper, 19 Mill Rd., Harvard, MA 01451, Tel: 978-456-8622 All Chairs of standing Advertising Manager: Vincent J. Gale, P.O. Box 1150, Marshfield, MA 02050, Committees, the editor Email: Manager-vincegale(at)mboservices.net; Tel: 781-837-0424 of THE NUCLEUS, and Contributing Editors: Morton Hoffman, Feature Editor; Dennis Sardella, Book Reviews the Trustees of Section Calendar Coordinator: Sheila Rodman, email: srodman(at)konarka.com Funds are members of the Photographers: Morton Z. Hoffman and James Phillips Board of Directors. Any Coun cilor of the American Chemical Soci- Proofreaders: Donald O. Rickter, Vivian K. Walworth, Mindy Levine ety residing within the section area is an ex Webmaster: Roy Hagen officio member of the Board of Directors. Copyright 2012, Northeastern Section of the American Chemical Society, Inc. The Nucleus April 2012 3 April Historical Events In Corporate Patrons $2000 - or more AstraZeneca Pharmaceuticals Chemistry Eisai Pharmaceuticals Leopold May, The Catholic University of America, Washington, DC 20064 EMD Serono Genzyme Corp. April 4, 1867 acids and their significance for in - Johnson Matthey A pioneer in clinical chemistry, Otto formation transfer in living material. Merck & Co. Folin, was born on this day. He April 10, 1790 Novartis engaged in the systematic develop- The U. S. Patent Office was estab- Pfizer Inc. ment of “micromethods”; the use of lished on this date according to Arti- Schering Corp. colorimetry in biochemistry using cle 8, Section 1 of the Constitution. Strem Chemicals, Inc. the Duboscq colorimeter; and the The first patent was granted to Vertex Pharmaceuticals use of an enzyme for analytical pur- Samuel Hopkins on potash and pearl $1000-$1999 poses: urease to measure urea. With ash. Boehringer Ingelheim Vintila Ciocalteu, he developed the GlaxoSmithKline “Phenol Reagent” for use in protein April 10, 1887 Irix Pharmaceuticals analysis. That is the basis of the One hundred and twenty-five years Lyophilization Services of NE Lowry method for protein determi- ago, Bernardo A. Houssay was born. Sundia Meditech nation. He received the Nobel Prize in Yes Bank Physiology or Medicine in 1947 $300-$999 April 6, 1928 with Gerty T. Cori and Carl F. Cori Cambridge Major Labs James D. Watson, born on this date, for their research on the hormone of conducted research on the double Girindus the anterior pituitary lobe and its Merrimack Consultants helix structure of DNA.
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