Organic

William P. Dailey

Photo: 
First Name: 
William P.
Last Name: 
Dailey
Official Title: 
Associate Professor of Chemistry

Organic Chemistry

Contact Information
Office Location: 
551 N, Lab: 507 N
Email: 
dailey@sas.upenn.edu
Phone: 
(215) 898-2704
Education: 

 

  • B.S. University of Connecticut (1979)
  • Ph.D. Dartmouth College (1983)
  • Postdoctoral Fellow, Yale University (1983-85)
  • Alfred P. Sloan Research Fellow (1990-94)
  • Lindback Award for Teaching Excellence (1992)
Research Interests: 

 

For many years the Dailey group has been involved in the areas of reactive intermediates, strained-ring chemistry, computational chemistry, matrix isolation, and organo-fluorine chemistry.

More recently we have turned our attention to the study of the mechanism of anesthesia. Many of the currently used inhalation anesthetics are small fluorinated molecules. One of the currently most widely used intravenous anesthetics is Propofol, a drug which allegedly contributed to the demise of Michael Jackson. Anesthetics are some of the most dangerous drugs currently used today, and their mechanism of action (both good and bad) remains largely unknown. New photoaffinity anesthetic compounds which mimic anesthetics but which can be photoactivated so that they can bind to potential molecular targets are being developed in our group. Using these compounds we are investigating the mechanism of anesthesia in collaboration with Dr. Roderick Eckenhoff's group at the School of Medicine at Penn. This collaboration was recently highlighted in C&E News.

 

Structures of several currently used anesthetics and the corresponding photoaffinity labeling analogs prepared in our laboratory.

Selected Publications: 

 

Michael A Hall, Jin Xi, Chong Lor, Shuiping Dai, Robert Pearce, William P. Dailey, Roderic G. Eckenhoff , "AziPm, photoactive analog of the intravenous general anesthetic, propofol", J. Med. Chem., 2010, 53, 5667 - 5675. 

 

Jerome Henin, William P. Dailey, Grace Brannigan, Roderic Eckenhoff, Michael L. Klein, "An Atomistic Model for Simulations of the General Anesthetic Isoflurane", J. Phys. Chem. B. 2010, 114(1), 604 - 612.

 

Roderic G. Eckenhoff, Jin Xi, Motomu Shimaoka, Aditya Bhattacharji, Manuel Covarrubias, William P. Dailey, "Azi-isoflurane, a photolabel analog of the commonly used inhaled general anesthetic, isoflurane", ACS Chemical Neuroscience, 2010, 1, 139 - 145.

 

L. Sangeetha Vedula, Grace Brannigan, Nicoleta J. Economou, Jin Xi, Michael A. Hall, Renyu Liu, Matthew J. Rossi, William P. Dailey, Kimberly C. Grasty, Michael L. Klein, Roderic G. Eckenhoff, Patrick J. Loll, "A Unitary Anesthetic Binding Site at High Resolution" J. Biol. Chem., 2009, 284, 24176-24184.

 

Jin Xi, Renyu Liu, Matthew J. Ross, Jay Yang, Patrick J. Loll, William P. Dailey, and Roderic G. Eckenhoff, "Photoactive Analogues of the Haloether Anesthetics Provide High-Resolution Features from Low-Affinity Interactions", ACS Chem. Biol., 2006, 1 , 377-384.

 

Tomas Martinu and William P. Dailey, "On the Reactivity of 1-Chloro-3-phenyldiazirines", J. Org. Chem., 2006, 71, 5012-5015.

 

Tomas Martinu and William P. Dailey, "Synthesis of Carboalkoxychloro- and Bromodiazirines", J. Org. Chem., 2004, 69, 7359-7362.

 

Roderic G. Eckenhoff, Frank Knoll, Eric P. Greenblatt, William P. Dailey " A Photolabel Mimic for the Inhaled Haloalkane Anesthetics", J. Med. Chem., 2002, 45, 1879 - 1886.

 

Dana R. Reed, Steven R. Kass, Kathleen R. Mondanaro, William P. Dailey "Formation of 1 1-Bicyclo[1.1.1]pentyl Anion and an Experimental Determination of the Acidity and C-H Bond Dissociation Energy of 3-t-Butylbicyclo[1.1.1]pentane", J. Am. Chem. Soc., 2002; 124(11); 2790-2795.

 

T. Martinu and W.P. Dailey " Facile One-Pot Preparation of 3-Chloro-2-(chloromethyl)propene and an Ab Initio Study of the Deamination Reaction of Nitrosoaziridine", J. Org. Chem. 2000, 65(20); 6784-6786.

 

T. Hirayama et al. "Responsive-to-Antagonist, a Menkes/Wilson disease-related copper transporter, is required for ethylene signaling in Arabidopsis", Cell 1999, 97, 383-393.

 

D. L. S. Brahms and W. P. Dailey "Fluorinated Carbenes", Chem. Rev. 1996, 96, 1585-1632.

 

T. D. Golobish and W. P. Dailey "Synthesis and Structure of Bishomohexaprismanedione", Tetrahedron Lett. 1996, 37, 3239 - 3242.

 

D. L. S. Yokotsuji et al. "Generation, Direct Observation under Matrix-isolation Conditions and Ab Initio Calculations for 2-Azacyclopenta-2, 4-dien-1-one", J. Phys. Chem. 1995, 99, 15870 - 15873 .

 

C. A. Jacobs, J. C. Brahms, W. P. Dailey, K. Beran and M. D. Harmony "Synthesis, Microwave Spectrum, and Ab Initio Calculations for Difluorocyclopropenone", J. Am. Chem. Soc. 1992, 114, 115-121.

 

M. A. Forman and W. P. Dailey "The Lithium Perchlorate-Diethyl Ether Rate Acceleration of the Diels-Alder Reaction: Lewis Acid Catalysis by Lithium Ion", J. Am. Chem. Soc. 1991, 113, 2761-2762.

Courses Taught: 

 

  • Chemistry 241
  • Chemistry 242
  • Chemistry 541

David M. Chenoweth

Photo: 
First Name: 
David M.
Last Name: 
Chenoweth
Official Title: 
Associate Professor of Chemistry

Organic and Bioorganic Chemistry

Contact Information
Office Location: 
2002 IAST, lab: 2020,2080,2100 IAST
Email: 
dcheno@sas.upenn.edu
Phone: 
215-­573-­1953
Admin Support: 
Education: 
  • B.S. Indiana University-Purdue University Indianapolis (1999)
  • Organic Chemist, Eli Lilly & Co., Indianapolis, IN (2000 – 2004)
  • Ph.D. California Institute of Technology (2009)
  • Kanel Foundation Predoctoral Fellow (2007 – 2009)
  • Caltech Herbert Newby McCoy Award (2009)
  • NIH/NIGMS Postdoctoral Fellow, Massachusetts Institute of Technology (2009 – 2010)
Research Interests: 

Research in the Chenoweth laboratory is grounded in organic chemistry and molecular recognition with applications to biological and materials problems. We synthesize molecules and study their properties and interactions for a broad range of applications in bioorganic and materials chemistry. We are particularly interested in the design and synthesis of new molecules that can modulate nucleic acid and protein structure. Additionally, we are equally interested in the synthesis of new materials with sensing and self-assembly properties.

 

Undergraduate students, graduate students, and postdoctoral researchers are exposed to a diverse array of topics including organic chemistry, synthesis, bioorganic chemistry, macromolecular structure (nucleic acids and proteins), biochemistry, and polymer chemistry.

Selected Publications: 

Zhang, Yitao; Malamakal, Roy M.; Chenoweth, David M. “Aza-Glycine Induces Collagen Hyperstability” J. Am. Chem. Soc. 2015, ASAP. DOI: 10.1021/jacs.5b04590. See Chemical & Engineering News story by Stu Borman: “Chemical Modification Is Best Ever At Strengthening And Stabilizing Collagen” Chemical & Engineering News, Volume 93, Issue 38, p. 7, News of The Week.

 

Zhang, Yitao; Malamakal, Roy M.; Chenoweth, David M. “A Single Stereodynamic Center Modulates the Rate of Self-Assembly in a Biomolecular System” Angew. Chem. Int. Ed. 2015, 54, 10826-10832.

 

Suh, Sung-Eun; Barros, Stephanie A.; Chenoweth, David M. “Triple Aryne–Tetrazine Reaction Enabling Rapid Access to a New Class of Polyaromatic Heterocycles” Chemical Science 2015, 6, 5128-5132.

 

Tran, Mai N.; Chenoweth, David M. “Synthesis and Properties of Lysosome-Specific Photoactivatable Probes for Live-Cell Imaging” Chemical Science 2015, 6, 4508-4512.

 

Barros, Stephanie A.; Chenoweth, David M. “Triptycene-Based Small Molecules Modulate (CAG)·(CTG) Repeat Junctions" Chemical Science 2015, 6, 4752-4755.

 

Tran, Mai N.; Chenoweth, David M. “Photoelectrocyclization as an Activation Mechanism for Organelle Specific Live-Cell Imaging Probes” Angew. Chem. Int. Ed. 2015, 54, 6442-6446.

 

Ballister, Edward R.; Ayloo, Swathi; Chenoweth, David M.; Lampson, Michael A.; Holzbaur, Erika L.F. “Optogenetic Control of Organelle Transport Using a Photocaged Chemical Inducer of Dimerization” Current Biology 2015, 10, R407-R408.

 

Ballister, Edward R.; Aonbangkhen, Chanat; Mayo, Alyssa M.; Lampson, Michael A.; Chenoweth, David M. "Localized Light-Induced Protein Dimerization in Living Cells using a Photocaged Dimerizer” Nature Communications 2014, 5, 5475.

 

Barros, Stephanie A.; Chenoweth, David M. "Recognition of Nucleic Acid Junctions Using Triptycene-Based Molecules” Angew. Chem. Int. Ed. 2014, 53, 13746-13750.

 

Rarig, Robert-André F.; Tran, Mai N.; Chenoweth, David M. "Synthesis and Conformational Dynamics of the Reported Structure of Xylopyridine A” J. Am. Chem. Soc. 2013, 135, 9213–9219, ASAP.

 

Chenoweth, David M.; Meier, Jordan L.; Dervan, Peter B. "Pyrrole-Imidazole Polyamides Distinguish Between Double-Helical DNA and RNA” Angew. Chem. Int. Ed. 2013, 52, 415-418.

 

Weizmann, Yossi; Chenoweth, David M.; Swager, Timothy, M. "DNA−CNT Nanowire Networks for DNA Detection” J. Am. Chem. Soc. 2011, 133, 3238–3241.

 

Chenoweth, David M.; Dervan, Peter B. “Structural Basis for Cyclic Py-Im Polyamide Allosteric Inhibition of Nuclear Receptor Binding” J. Am. Chem. Soc. 2010, 132, 14521. Selected for the cover of JACS Oct. 20, 2010, Vol 132, Issue 41. Covered by Chemical and Engineering News Sept. 27, 2010 issue, “Putting DNA in a Bind”.

 

Weizmann, Yossi; Chenoweth, David M.; Swager, Timothy, M. “Addressable Terminally-Linked DNA-CNT Nanowires” J. Am. Chem. Soc. 2010, 132, 14009.

 

Weizmann, Yossi; Lim, Jeewoo; Chenoweth, David M.; Swager, Timothy, M. “Regiospecific Synthesis of Au-Nanorod/SWCNT/Au-Nanorod Heterojunctions” Nano Lett. 2010, 10, 2466.

 

Chenoweth, Kimberly; Chenoweth, David M.; Goddard III, William A. “Cyclooctyne-based Reagents for Uncatalyzed Click Chemistry: A Computational Survey” Org. Biomol. Chem. 2009, 7, 5255.

 

Chenoweth, David M.; Harki, Daniel A.; Dervan, Peter B. “Oligomerization Route to DNA Binding Py-Im Polyamide Macrocycles” Org. Lett. 2009, 11, 3590.

 

Chenoweth, David M.; Dervan, Peter B. “Allosteric Modulation of DNA by Small Molecules” Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 13175. Covered by Nature News: "Get into the groove" Nature 2009, 460, 669. Also selected by the Stanford Synchrotron (SSRL) as a science highlight for November 2009.

 

Chenoweth, David M.; Harki, Daniel A.; Dervan, Peter B. “Solution-Phase Synthesis of Pyrrole-Imidazole Polyamides” J. Am. Chem. Soc. 2009, 131, 7175.

 

Chenoweth, David M.; Harki, Daniel A.; Phillips, John W.; Dose, Christian; Dervan, Peter B. “Cyclic Pyrrole-Imidazole Polyamides Targeted to the Androgen Response Element” J. Am. Chem. Soc. 2009, 131, 7182.

 

Chenoweth, David M.; Chenoweth, Kimberly; Goddard III, William A. “Lancifodilactone G: Insights about an Unusually Stable Enol” J. Org. Chem., 2008, 73, 6853.

 

Dose, Christian; Farkas, Michelle E.; Chenoweth, David M.; Dervan, Peter B. “Next Generation Hairpin Polyamides with (R)-3,4-Diaminobutyric Acid Turn Unit” J. Am. Chem. Soc., 2008, 130, 6859.

 

Chenoweth, David M.; Viger, Anne; Dervan, Peter B. “Fluorescent Sequence-Specific dsDNA Binding Oligomers” J. Am. Chem. Soc., 2007, 129, 2216. Covered by Chemical and Engineering News.

 

Chenoweth, David M.; Poposki, Julie A.; Marques, Michael A.; Dervan, Peter B. “Programmable oligomers targeting 5'-GGGG-3' in the minor groove of DNA and NF-k B binding inhibition” Bioorg. Med. Chem., 2007, 15, 759.

 

Doss, Raymond M.; Marques, Michael M.; Foister, Shane; Chenoweth, David M.; Dervan, Peter B. “Programmable Oligomers for Minor Groove DNA Recognition” J. Am. Chem. Soc., 2006, 128, 9074.

 

Nurok, D.; Frost, M. C.; Chenoweth, D. M. “Separation using planar chromatography with electroosmotic flow” J. Chromatogr., A, 2000, 903, 211. 

 

Nurok, David; Frost, Megan C.; Pritchard, Cary L.; Chenoweth, David M. “The performance of planar chromatography using electroosmotic flow” J. Planar Chromatogr.-Mod. TLC, 1998, 11, 244.

Department of Chemistry

231 S. 34 Street, Philadelphia, PA 19104-6323

215.898.8317 voice | 215.573.2112 fax | web@chem.upenn.edu

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