William P. Dailey
Associate Professor of Chemistry

Overview

Organic Chemistry

Research

 

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.

Teaching

 

  • Chemistry 241
  • Chemistry 242
  • Chemistry 541

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)

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.

Office Location

551 N, Lab: 507 N

Phone

(215) 898-2704

Department of Chemistry

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

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