Mitchell A. deLong, Ph. D.

Adjunct Professor of Chemistry

Duke University 101 Gross Chemical Building
Box 90347
Durham, NC  27708-0347

madelong@duke.edu

 

 

Research Interests:   Arene-Olefin Photochemistry; Green Chemistry, Sulfur Radical Chemistry;
Medicinal Chemistry and Drug Design, Total Synthesis of Complex Natural Products

 

Educational Geneology:  Ph.D. 1991 Stanford University, under Professor Paul Wender

 

 

beta-Silyl Arene-Olefin Photochemistry

 

 

This is the X-ray crystal structure of a 5.5.6 syn-cis-syn ring system with a sulfonyl benzoic acid ester attached. This was synthesized in three steps from benzyltrimethylsilane.

 

 

 

Patent and Publication List

 

Scientific Meeting Posters & Presentations

1.       Chawla, S; deLong, MA; Visscher, MO; Wickett, RR; Boissy, RE Mechanism of Tyrosinase Inhibition by DeoxyArbutin and Second Generation Derivatives Thereof.  19th International Pigment Cell Conference, Reston, VA Sept 2005

2.       deLong, MA; Visscher, MO; Boissy, RE Synthesis, SAR, in vivo, and Clinical Data of the DeoxyArbutin Class of Tyrosinase Inhibitors  Abstracts of Papers of the American Chemical Society 2005 229 (San Diego, CA) March 13-15 2005. MEDI-402.

3.       Cohen, SL; deLong, MA An Arene-Olefin Photocyclization Approach to the Total Synthesis of (+)-Arnicenone Abstracts of Papers of the American Chemical Society 2004 227 (Anaheim, CA) April 2004. oral presentation.

4.       deLong, MA; Mathews, JA; Wireko, FC; Ritter, AL; Gudmundsdöttir, AD Air-Initiated Reactions: Vinyl Cyclopropane Openings with Aryl Sulfur Radicals   Abstracts of Papers of the American Chemical Society 2004 227 (Anaheim, CA) April 2004 oral presentation.

5.       Mathews, JA; deLong, MA; Cohen, SL; Wireko, FC; Ritter, AL; Gudmundsdöttir, AD  b-Silyl Arenes: Arene-Olefin Photocyclization Substrates Abstracts of Papers of the American Chemical Society 2003 225 (New Orleans, LA) March 2003 oral presentation.

6.       Fossum, RD; deLong, MA; McCorkle, RM; Smith, LJ; Fuentes, GR Preparation of Sulfoxide-Containing Polymers and Their Potential Use as Substantive Skin Moisturizing Agents paper #POLY223 Abstracts of Papers of the American Chemical Society 2003 225 (New Orleans, LA) March 2003 published notes.

7.       Mathews, JA; deLong, MA; Gudmundsdottir, AD; Ritter, AL; Wireko, FC  b-Silyl Arenes: Novel Arene-Olefin Photocyclization Substrates 2002 Oespar Symposium, Oct. 25 2002 U. of Cincinnati, Cincinnati, OH

8.       Ebetino, FH; Soper, DL; Dirr, ML; Lundy, MW; Mieling, G; Chmielewski, P; Froman, C; Farmer, R; Wos, JA; deLong, MA Pharmacological Studies and SAR of 1-Phosphinico Prostaglandin F Analogs: The Development of New Bone Anabolic Agents Naff Symposium, April 26 2002 U. of Kentucky Lexington, KY

9.       Ebetino, FH; Soper, DL; Dirr, ML; Lundy, MW; Mieling, G; Chmielewski, P; Froman, C; Farmer, R; Wos, JA; deLong, MA  Pharmacological Studies and Structure-Activity Relationships of 1-Phosphinico-Prostaglandin F Receptor Ligands; The Development of New Bone Anabolic Agents J. Bone and Mineral Research 2001 16, Supp. [1], S490.

10.    deLong, MA; Wos, JA; Wang, Y; Soper, DL; Dirr, ML The Synthesis and SAR of W-Chain Acetylenic Prostaglandin F Analogs as Potential Bone Anabolic Agents Abstracts of Papers of the American Chemical Society 2001 222, (Chicago, IL) August 26-30, 2001, MEDI-193 oral presentation.

11.    Soper, DL; deLong, MA; Wos, JA; Wang, Y; De, B; Dirr, ML; Chemilewski, P; Yoa, W; Lundy, MW; Bosch, GK; Mootz, M   Discovery of PG-3366466, a Selective Prostaglandin F Receptor Agonist for the Treatment of Osteoporosis Abstracts of Papers of the American Chemical Society 2001 222, (Chicago, IL) August 26-30, 2001, MEDI-194 oral presentation.

12.    Bosch, GK; deLong, MA Enantiospecific Synthesis of PGE-3366466, a Selective Prostaglandin F Receptor Agonist for the Treatment of Osteoporosis Abstracts of Papers of the American Chemical Society 2001 222, (Chicago, IL) August 26-30, 2001, ORGN-383.

13.    Ebetino, FH; Soper, DL; Dirr, MJ; Lundy, MW; Mieling, G; Stella, ME; Bodman, M; Wos, JA; deLong, MA The Synthesis and SAR of 1-Phosphinico-Prostaglandin F Analogs; Development of a Pre-Clinical Candidate for the Treatment of Osteoporosis International Congress on Phosphorous Chemistry XV, 2001 Tokyo, Japan, June 2001 Oral Presentation

14.    McCorkle, RM; Fuentes, GR; deLong, MA Osmium-free or Reduced-Osmium-Demand Oxidative Cleavage Reactions Using Sodium Periodate in Acetic Acid Solutions. Abstracts of Papers of the American Chemical Society 2001 221, Part 2 p. U185, San Diego, CA April 1-5, 2001 502-ORGN.

15.    Fuentes, GR; McCorkle, RM; Wireko, FC; Mootz, MR; deLong, MA Direct Reductive Amination of Cyclic Ketones with Ammonia:  Preparation and X-Ray Crystal Structure of Di(4-Thianyl)Amine Abstracts of Papers of the American Chemical Society 2001 221, Part 2 U184, San Diego, CA April 1-5, 2001, 496-ORGN.

16.    De, B; deLong, MA; Dirr, MJ; Lundy, MW; Mieling, G; Soehner, ME; Soper, DL; Wang, Y; Wos, JA  Prostaglandin FP Receptor Agonists as Bone Anabolic Agents for the Treatment of Osteoporosis.  27th National Med. Chem. Symposium June 13-17, 2000, Kansas City, MO.

17.    Strader, KH; Wehmeyer, KR; Gu, Z, Russell, AF; Regg, BT; Wos, JA. Soper, DL; deLong, MA; Knight, PA; Ezra, FS Inglin, TA  Identification of Structural Isomers and Major Degradation Products of 5,6-cis, 15-S Fluprostenol Using HPLC-NMR and HPLC-MS.  Midwest Regional ACS meeting, Covington, KY, May 12-15, 2000.

18.    Vedernikov, YP; Hartke, JR; deLong, MA; Saade, GR; Garfield, RE Effect of Selected Prostaglandins on Contractility of Rat and Human Uterine Tissues with and without Sex Hormone Replacement Society for Gynecological Investigators Annual meeting 2000.

19.    Soper, DL; Wang, Y; De, B; deLong, MA; Dirr, MJ; Soehner, ME; Lundy, MW; Mieling, GE; Wos, JA  The Design and Synthesis of Selective Prostaglandin Analogs as Bone Anabolic Agents for the Potential Treatment of Osteoporosis. Sixth International Conference on Eicosanoids & Other Bioactive Lipids in Cancer, Inflammation and Related Diseases, Boston, MA, Sept. 12-15, 1999.  Prostaglandins and Other Lipid Mediators 59 1999 88. oral presentation with published notes.

20.    Soper, DL; deLong, MA; Wos, JA; Wang, Y; Desmarias, W; De, B; Dirr, MJ; Hartke, JR Synthesis of 17-Phenyl Saturated Prostaglandin F Analogs via a Key 13-Aldehyde Abstracts of Papers of the American Chemical Society, 1999 218, Part 1, 263-MEDI.

21.    Wang, Y; Wos, JA; deLong, MA; Dirr, MJ; Soper, DL; De, B The Synthesis of 17-Phenyl Saturated Prostaglandin F Analogs via a Useful 15, 16-Epoxide Intermediate AIMECS 99-Sept. 1999 37 Beijing, PRC.

22.    deLong, MA; Wos, JA; Soper, DL; Wang, Y; Amburgey, JS; Miley, CJ; Lundy, MW; Hartke; JR; Froman, C; Jankowsky, MA; Soehner, ME; Combs, KS; De, B 17-Phenyl Saturated Prostaglandin F Analogs:  Potent, Selective Human FP Receptor Agonists with Bone Anabolic Effects in the Aged, OVX Rat Model. AIMECS 99-Sept. 1999 36 Beijing, PRC.

23.    deLong, MA; Hartke, JR; Jankowsky, ML; Soehner, ME; Wos, JA; Soper, DL; Lundy, MW Tetrahydrofluprostenol, a 17-Phenyl Saturated Prostanoid FP Receptor Agonist, is a Bone Anabolic Agent in the Aged, OVX Rat. Journal of Bone and Mineral Research, 1999, 14, Supp. 1, S275.

24.    deLong, MA; Dirr, MJ; Soper, DL; Wang, Y; Lundy, MW; Wos, JA 17-Phenyl Saturated PGF2a Analogs Retain hFP Receptor Activity and Increase Selectivity. Journal of Bone and Mineral Research, 1999, 14, Supp. 1, S274.

25.    Lundy, MW; deLong, MA; Combs, KS; Gross, GJ; Soehner, ME; Hartke, JR  Restoration of Cancellous Architecture and Increased Bone Strength in Aged Osteopenic Rats Treated with Fluprostenol Journal of Bone and Mineral Research, 1999, 14, Supp. 1, S401.

26.    Hartke, JR; Jankowsky, ML; deLong, MA; Soehner, ME; Jee, WSS; Lundy, MW  Prostanoid FP Agonists Build Bone in the Ovariectomized Rat. Journal of Bone and Mineral Research, 1999, 14, Supp. 1, S207.

27.    Hicks, CR; Dirr, MJ; Charest, RP; Soper, DL; Ruble, AM; Hartke, JR; deLong, MA Functional Activity and Receptor Binding of Misoprostol, Sulprostone and 9-Hydroxy Variants at Cloned Human EP3 and EP1 Receptors. FASEB Journal 1998 12, A1459.

28.    Dirr, MJ; Hicks, CR; Charest, RP; Soper, DL; Ruble, AM; Hartke, JR; deLong, MA Functional Activity and Receptor Binding of 17-Phenyl-17-trinor PGE2, 9-Methylene-9-deoxy PGE2 and 9-Substituted Analogs at Cloned Human EP1 & EP3 Receptors. FASEB Journal 1998 12, A1386.

29.    Soper, DL; Brann, M; Amburgey, JS; Miley, CJ; Wos, JA; Wang, Y; Hartke, JR; De, B; deLong, MA  Activity and Receptor Selectivity of Misoprostol, Sulprostone and Their 9-Hydroxy Variants at Cloned Human EP3 and EP1 Receptors.  Abstracts of Papers of the American Chemical Society, 1998 215, Part 1, A050-MEDI.

30.    Miley, CJ; Amburgey, JS; Soper, DL; Brann, M; Wos, JA; Wang, Y; Hartke, JR; De, B; deLong, MA  Activity and Receptor Selectivity of 17-Phenyl-Trinor PGE2, 9-Methylene-9-Deoxy-PGE2, and 9-Substituted Analogs at Cloned Human EP1 and EP3 Receptors. Abstracts of Papers of the American Chemical Society, 1998 215, Part 1, B050-MEDI.

31.    deLong, MA; Jee, WSS; Jankowsky, M; Soehner, ME; Pierce, SA; Ma, YF; Hartke, JR; Lundy, MW Bone Anabolic Effects of PGE1 in Aged, Ovariectomized Rats Measured by DXA, pQCT & Histology Journal of Bone and Mineral Research, 1997 12, Supp. 1, S494.

32.    deLong, MA; Miley, CJ; Amburgey, JS; Roof, SL; Pierce, SA; Lundy, MW Synthesis and Bone Anabolic Effects of the Ethyl Ester of BW245C and Analogs, Specific Prostaglandin D (DP) Receptor Agonists. Abstracts of Papers of the American Chemical Society, 1997 213, Part 2, 135-MEDI.

33.    Combs, KS; Roof, SL; Pierce, SA; deLong, MA; Diehl, JR; Whitaker, AM; Hartke, JR; Lundy, MW Bone Anabolic Effects of a Prostaglandin-D Receptor Agonist as Demonstrated by Histomorphometry and Peripheral Quantitative Computed-Tomography (pQCT) Measurement. Journal of Bone and Mineral Research, 1996 11, Supp. 1, T615.

34.    Roof, SL; deLong, MA; Charest, RP  Messenger-RNA Expression of Prostaglandin Receptors EP1, EP2, EP3 and EP4 in Human Osteoblast-Like Cells and 23 Human Tissues. Journal of Bone and Mineral Research, 1996 11, Supp. 1, S337.

35.    deLong, MA and St. John, LC  Chemistry and SAR of Potential Cholesterol Lowering Agents AIMECS '95, Sept. 1995, Tokyo, Japan.

36.    Wender, PA; Dore, TR; deLong, MA  Synthesis of the First trans, cis, cis, cis- [5.5.5.5] Fenestrane via Arene-Olefin Photocyclization.  Tenth Annual Johnson Symposium, Oct. 1995, Stanford University, Palo Alto, CA.

 

Patents and Patent Applications

1.       Toone, EJ; Epstein, DL; Challa, P; Snyder, PW;. Chen, X; deLong, MA Opthamological Drugs PCT Int. Appl. No. WO 06/047466 Chem Abstr. 2006, 412056 Published May 5, 2006, US Patent Application US2006-0135609A1, Published June 22, 2006.

2.       deLong, MA 2-Decarboxy-2-Phosphinico Prostaglandin Derivatives and Methods for Their Preparation US Patent Application US2005-0124588A1, Published June 9, 2005.

3.       deLong, MA 2-Decarboxy-2-Phosphinico Prostaglandin Derivatives and Methods for Their Preparation and Use. US Patent Application US2005-0124587A1, Published June 9, 2005, US Patent# 7074942, issued July 11, 2006.

4.       deLong, M.A. 2-Decarboxy-2-Phosphinico Prostaglandin Derivatives and Methods for Their Preparation and Use Chem Abstr. 2005: 420112. US Patent # 6,894,175, issued May 17, 2005.

5.       deLong, M. A.; Cohen, S. L. Nuclear Hormone Receptor Compounds, Products and Methods Employing Same.  US Patent Application US2004-0131648A1 Published July 8, 2004.

6.       deLong, M. A.; Biedermann, K. A.; Bissett, D. L.; Boyer, A. S.; Cohen, S. L.; Snider, C. E. Nuclear Hormone Receptor Ligands, Products and Methods Employing Same PCT Int. Appl. No. WO-04/037213 Chem Abstr. 2004, 368900 Published May 6, 2004.

7.       deLong, M. A.; Fossum, R. Underiner, T., McIver, J.; Youngquist, R. S. Methods of Using Acyclic Sulfoxide Polymers for Moisturizing Applications PCT Int. Appl. No. pending; Chem Abstr. pending. filed, Mar. 15. 2001.

8.       deLong, M. A.; Fossum, R. Underiner, T.,  McIver, J.; Youngquist, R. S. Cyclic Sulfoxide Monomers, Polymers Made Therefrom, and Methods for Their Use PCT Int. PCT Int. Appl. No. pending; Chem Abstr. pending. filed, Mar. 15 2001.

9.       deLong, M. A.; Hatz, D.; McCorkle, R. M. Compounds, Compositions and Methods for Insect Control PCT Int. Appl. No. WO-02/067680; Chem Abstr. 2002: 98841 published Sept. 6, 2002.

10.    deLong, M. A.; Youngquist, S. A.; McIver, J. R.  Compositions and Methods for Treating Hair Loss Using Oximyl- and Hydroxylamino- Prostaglandins PCT Int. Appl. No. WO-01/74307; published Oct. 11, 2001.

11.    deLong, M. A.; Youngquist, S. A.; McIver, J. R.  Compositions and Methods for Treating Hair Loss Using Non-Naturally Occurring Prostaglandins PCT Int. Appl. No. WO-01/74315; published Oct. 11, 2001.

12.    deLong, M. A.; Youngquist, S. A.; McIver, J. R.  Cosmetic and Pharmaceutical Compositions and Methods Using 2-Decarboxy-2-Dephosphinico Derivatives of Prostaglandins   PCT Int. Appl. No. WO-01/74314; published Oct. 11, 2001.

13.    deLong, M. A.; Youngquist, S. A.; McIver, J. R.  Compositions and Methods for Treating Hair Loss Using C16-C20 Aromatic Tetrahydro Prostaglandins PCT Int. Appl. No. WO-01/74315; P&G Case No. 7996P filed, April 2000, published Oct. 11, 2001.

14.    deLong, M. A.; Wos; J. A.; De, B.; Soper, D. L.  A Process for Making Novel 2-Decarboxy-2-Halo Prostaglandin Intermediates  filed October 9, 1999.

15.    deLong, M. A.  A Process for Making Novel 2-Decarboxy-2-Halo Prostaglandin Intermediates Filed Aug. 8, 1999.

16.    deLong, M. A.; Wos; J. A.; De, B.; Ebetino, F. H.  Novel 2-Decarboxy-2-Phosphinico Prostaglandin F Analogs   PCT Int. Appl. No. WO 110873A1; Chem Abstr. 2001, 2001:115155; US Patent # 6372730 issued April 16, 2002.

17.    Hartke, J. M.; Lundy, M. W. Method of Increasing Bone Volume Using FP Agonists and Antiresorptive Agents PCT Int. Appl. No.; Chem Abstr. 2000 Filed March 5, 1999; published September 8, 2000.

18.    Hartke, J. M.; Lundy, M. W.; deLong, M. A.  Method of Increasing Bone Volume Using Non-naturally-Occurring Selective EP1 & FP Agonists PCT Int. Appl. No. WO-2000/051616; Chem Abstr. 2000, 133:188461; published September 8, 2000.

19.    Hartke, J. M.; Lundy, M. W.; deLong, M. A.  A Method of Increasing Bone Volume Using Non-Naturally-Occurring Prostaglandin EP1 Agonists PCT Int. Appl. No. WO-2000/051585; Chem Abstr. 2000, 133:227791; published September 8, 2000.

20.    deLong, M. A.; Wos; J. A.; De, B.; Soper, D. L. A Process for Making 13, 14-Dihydro-15-Substituted-15-Pentanor or 17-Trinor Prostaglandin F1a Analogs   PCT Int. Appl. No. WO-2000/051977; Chem Abstr. 2000, 133:222495; published September 8, 2000.

21.    deLong, MA; Wos, J. A.; De, B.; Soper, D. L. C16 Unsaturated FP-Selective Prostaglandin Analogs   PCT Int. Appl. No. WO-2000/051979; Chem Abstr. 2000, 133:222497; published September 8, 2000. US Patent #6586463; July 1, 2003.

22.    deLong, MA; Amburgey, J. S.; Wos, J. A.; De, B.; Soper, D. L. C16 Unsaturated FP-Selective Prostaglandin Analogs PCT Int. Appl. No. WO-2000/051980; Chem Abstr. 2000, 133:222498. US Patent #6451859, Sept 17, 2002.

23.    deLong, MA; Amburgey, J. S.; Wos, J. A.; De, B.; Soper, D. L.  Preparation of C11-Oximido Prostaglandins Useful as FP Agonists   PCT Int. Appl. No. WO 9950242; Chem Abstr. 1999, 131:257381; US Patent #6444840, Sept 3, 2002.

24.    deLong, MA; Amburgey, J. S.; Wos, J. A.; De, B.; Soper, D. L. Preparation of C11-Oximido Prostaglandins to Treat Bone Disorders and Glaucoma   PCT Int. Appl. No. WO 9950241; Chem Abstr. 1999, 131:271764; US Patent #6410780, June 25, 2002.

25.    Kvalnes, K. L.; deLong, M. A.; Bradbury, B. J.; Motley, C. B.; Carter, J. D. Skin Lightening Compositions Filed Aug. 13, 1998, US Patent # 6537527, March 25, 2003.

26.    Amburgey, J. S.; De, B.; Dai, G.; Soper, D. L.; Wos, J. A.; deLong, M. A.  A Process for Making 13, 14-Dihydro-15, 16, or 17-Substituted-16-Tetranor or 17-Trinor Prostaglandin F1a Analogs   PCT Int. Appl. No. WO-9912899 Chem Abstr. 1999, 194119.

27.    Wos, J. A.; deLong, M. A.; Amburgey, J. S.; De, B.; Dai, G.; Wang, Y.  A Process For Making 13, 14-Dihydro-15- 16- or 17-Substituted-16-Tetranor or 17-Trinor Prostaglandin F1a Analogs   PCT Int. Appl. No. WO-9912897; Chem Abstr. 1999, 194117, US Patent #6066751, May 23, 2000.

28.    Amburgey, J. S.; De, B.; Dai, G.; Taylor, C. J.; Wos, J. A.; deLong, M. A. Aromatic C16 - C20 - Substituted Tetrahydro Prostaglandins Useful As FP Agonists   PCT Int. Appl. No. WO-9912896; Chem Abstr. 1999, 194116, US Patent #6107338, Aug. 22, 2000.

29.    deLong, M. A.; Amburgey, J. S.; De, B.; Dai, G.; Soper, D. A.; Wos, J. A.  Aromatic C16 - C20 - Substituted Tetrahydro Prostaglandins Useful as FP Agonists   PCT Int. Appl. No. WO-9912898; Chem Abstr. 1999, 194118, US Patent #6048895, Apr. 11, 2000.

30.    Wos, J.A.; deLong, M.A.; Amburgey, J.S.; De, B.; Dai, G.; Wang, Y. Aromatic C16 - C20 - Substituted Tetrahydro Prostaglandins Useful as FP Agonists   PCT Int. Appl. No. WO-9912895; Chem Abstr. 1999, 194115, US Patent #5977173, Nov. 2, 1999.

31.    Hartke, J.R.; Lundy, M.W.; deLong, M.A. Method of Increasing Bone Volume PCT Int. Appl. No. WO-9912551; Chem Abstr. 1999, 194005.

32.    Hartke, J. R.; Lundy, M. W.; deLong, M. A.  Method of Increasing Bone Volume Using Non-Naturally-Occurring FP Agonists   PCT Int. Appl. No. WO-9912550; Chem Abstr. 1999, 194004. US Patent #6156799, Dec 5, 2000.

33.    Kvalnes, K. L.; deLong, M. A.; Bradbury, B. J.; Motley, C. B.; Carter, J. D. Skin Lightening Compositions Containing Oxyphenol Derivatives WO-9523780; Chem Abstr. 1995, 123, 349869, US Patent #6068834, May 30, 2000.

 

Journal Publications

1.   Hamed, Saja H., Sriwiriyanont, Penkanok; deLong, Mitchell A.; Visscher Marty O.; Wickett, R. Randall; Boissy Raymond E.  Comparative Efficacy and Safety of a New Tyrosinase Inhibitory Agent, DeoxyArbutin.  Int J Cosmet Sci 28 (x) 2006 xxx-xxx.

2.       Boissy Raymond E.; Visscher Marty; deLong, Mitchell A. DeoxyArbutin: a Novel Reversible Tyrosinase Inhibitor with Effective in vivo Skin Lightening Potency.  Experimental Dermatology 14 (8) 2005 601-608.

3.       deLong, MA American Chemical Society - 227th National Meeting (Part XV), Medicinal Chemistry Division, Anaheim CA, USA IDdb Meeting Report 2004,March 28-April 2. (invited contribution)

4.       Vedernikov, Yuri P.; Hartke, James R.; deLong, Mitchell A.; Saade, George R.; Garfield, Robert E.  Sex Hormone Effects in Non-Pregnant Rat and Human Myometrium.  European J. Ob. Gyn. Repro. Bio. (2003 May 1) 2003 108 (1) 59-66.

5.       deLong, MA American Chemical Society - 225th National Meeting (Part XV), Organic Chemistry Division, New Orleans, LA, USA IDdb Meeting Report 2003, March 23-27. (invited contribution)

6.       Miller, L. A.; Baumgart, L. E.; Chew, G. H.; deLong, M. A.; Galloway, L. C.; Jung, K. W.; Merkler, K. A.; Nagle, A. S.; Poore, D. D.; Yoon, C. H.; Merkler, D. J. Glutathione, S-Substituted Glutathiones, and Leukotriene C4 as Substrates for Peptidylglycine a-Amidating Monooxygenase.  Arch. Biochem. Biophys. 412, 2003 3-12.

7.       Fossum, RD; deLong, MA; McCorkle, RM; Smith, LJ; Fuentes, GR   Preparation of Sulfoxide-Containing Polymers and Their Potential Use as Substantive Skin Moisturizing Agents. Polymer Preprints 44(1), 2003 870-871.

8.       Soper, DL; Wang, Y; De B; deLong, MA; Dirr, MJ; Soehner, ME; Lundy, MW; Mieling, GE; Wos, JA  The Design and Synthesis of Selective Prostaglandin Analogs as Bone Anabolic Agents for the Potential Treatment of Osteoporosis. Advances in Experimental Medicine and Biology 2002 (3) 507 303-7.

9.       Ebetino FH; Soper DL; Dirr MJ; Lundy MW; Mieling GE; Wos, JA; deLong MA; Liu XW   The Rational Design of Drugs with Phosphonic/Phosphinic Acids as Enzyme Inhibitors and Isosteric Receptor Ligands. Phos. Sul. Sil. Elements 2002 177(6-7), 1725-1729.

10.    Soper DL; Wang YL; De BW; deLong MA; Dirr MJ; Soehner ME; Lundy MW; Mieling GE; Wos JA The Design and Synthesis of Selective Prostaglandin Analogs as Bone Anabolic Agents for the Potential Treatment of Osteoporosis. Eicosanoids and other Bioactive Lipids in Cancer, Inflammation, and Radiation Injury 5, 2002 507, 303-307.

11.    Soper DL; Milbank JBJ; Mieling GE; Dirr MJ; Kende AS; Chen R; Bodman M; Lundy MW; De B; Stella ME; Ebetino FH; Wang Y; deLong MA.  Synthesis and Biological Evaluation of Prostaglandin-F Alkylphosphinic Acid Derivatives as Bone Anabolic Agents for the Treatment of Osteoporosis J. Med. Chem. 2001 44(24), 4157.

12.    Kende, AS; Milbank, JBJ; Ebetino, FH; deLong, MA Prostaglandin Phosphonic Acids through Homolytic Halo-decarboxylation of Prostaglandins F1a and F2a Tetrahedron Lett. 1999 40, (47) 8189.

13.    Soper, D.L.; Wang, Y.; De, B.; deLong, M.A.; Dirr, M.J.; Soehner, M.E.; Lundy, M.W.; Mieling, G.E.; Wos, J.A.  The Design and Synthesis of Selective Prostaglandin Analogs as Bone Anabolic Agents for the Potential Treatment of Osteoporosis. Presented at the 6th International Conference on Eicosanoids & Other Bioactive Lipids in Cancer, Inflammation and Related Diseases, Boston, MA, Sept. 12-15, 1999, No. 88 Prostaglandins & Other Lipid Mediators 1999 59 1-6 88.

14.    Wang, Y; Wos, JA; Dirr, MA; Soper, DL; deLong, MA; Mieling, G; De, B; Amburgey, J; Suchanek, E; Taylor, CJ The Design and Synthesis of 13, 14 - Dihydroprostaglandin F1a Analogs as Potent and Selective Ligands for the Human FP Receptor. J. Med. Chem. 2000 43(5), 945-952.

15.    Eichhold, TH; Kuhlenbeck, DL; Baker, TR; Stella, ME; Amburgey, JS; deLong, MA; Hartke, JR; Cruze, CA; Pierce, SA; Wehmeyer, KR  Use of Short HPLC Columns and Tandem-Mass Spectrometry (HPLC-MS/MS) for the Rapid Analysis of a Prostaglandin Analog, Fluprostenol in Rat Plasma. J. Chromatography B, Biomed. Sci. Appl.  2000, 741(2), 213-220.

16.    deLong, MA; Amburgey, JS; Taylor, CJ; Wos, JA; Soper, DL; Wang, Y; Hicks, R  Synthesis and in vitro Evaluation of Human FP-Receptor Selective Prostaglandin Analogs Bio. & Med. Chem Lett. 2000, 10 (14) 1519

17.    deLong, MA Prostaglandin Receptor Ligands: Recent Patent Activity. Investigational Drugs, 3(9) 2000, 1039-1052.

18.    Wang, Y; Soper, DL; Dirr, MJ; deLong, MA; De, B; Wos, JA The Synthesis and Human FP Receptor Binding Affinity of 13, 14-Dihydro Prostaglandin F1a Sulfonamides: Potential Treatments for Osteoporosis.  Chem. Pharm. Bull. 2000 48(9), 1332-1337.

19.    DeBlassio, JL; deLong, MA; Glufke, U; Kulathila, R; Merkler, KA; Vederas, JC; Merkler, DJ   The Amidation of Salicyluric Acid and Gentisuric Acid; A Possible Role for Peptidylglycine a-Amidating Monooxygenase in the Metabolism of Aspirin.  Arch. Biochem. Biophys. 2000 383, 46-55.

20.    Wilcox, B. J.; Ritenour-Rodgers, J.; Asser, A. S.; Baumgart, L. E.; Baumgart, M. A.; Boger, D. L.; DeBlassio, J. L.; deLong, M. A.; Glufke, U.; Henz, M. E.; King, L.; Merkler, K. A.; Patterson, J. E.; Robleski, J. J.; Vederas, J. C.; Merkler, D. J.  N-Acylglycine Amidation: Implications for the Biosynthesis of Fatty Acid Primary Amides. Biochemistry, 1999, 38(11), 3235-3245.

21.    Wender, PA; deLong; MA; Wireko, FC Novel oxidative rearrangement product of the first trans, cis, cis, cis-[5.5.5.5] fenestrane derivative. Acta Crystallographica Section C, 1997 53, Part 7, 954-956.

22.    Wender, PA; Dore, TM; deLong, MA An Arene-Alkene Photocycloaddition-Radical Cyclization Cascade - The First Syntheses of cis, cis, cis, trans-[5.5.5.5]-Fenestranes. Tetrahedron Letters, 1996 37(43), 7687-7690.

23.    deLong, MA Arene-Olefin meta-Photocyclizations and the Total Synthesis of (-) Subergorgic Acid.  Thesis Stanford University, 1992.

24.     Wender, PA; deLong; MA Total Synthesis of (+/-) Subergorgic Acid. Tetrahedron Letters 1990 31(38), 5429.

25.    Wender, PA; Ternansky, R; deLong, MA; Singh, S; Olivero, A.; Arene-Alkene Cycloadditions and Organic Synthesis. Pure & Appl. Chem. 1990 62(8), 1597.

Invited Talks and Sessions Chaired

1.       ‘DukeProst’ a Clinical Candidate for the Treatment of Glaucoma. Department of Chemistry, Duke University, Durham, NC  Scheduled, Fall 2006

2.       The Discovery and SAR of ‘Osteoprost’ a Preclinical Candidate for the Treatment of Osteoporosis. Department of Chemistry, University of New Hampshire, Durham, NH Sept 13, 2005.

3.       ‘Total Synthesis of Complex Molecules’ Session Chair 229th National ACS meeting, San Diego, CA   March 13-18, 2005.

4.       Prostaglandin Synthesis in the Twenty-First Century-Plenary Lecture, Sixth Annual Florida Heterocyclic Conference, February 15, 2005.

5.       Selective Prostaglandin FP Ligands as Bone-Anabolic Agents 36th Midwest Regional ACS meeting, Indianapolis, IN, June 2-4, 2004.

6.       ‘Total Synthesis of Complex Products’ Session Chair 227th National ACS meeting, Anaheim, CA   March 28-April 1, 2004.

7.       The Discovery and SAR of ‘Osteoprost’ a Preclinical Candidate for the Treatment of Osteoporosis Department of Chemistry, University of Florida, Gainesville, FL Feb 12, 2004.

8.       The Discovery and SAR of a Preclinical Candidate for the Treatment of Osteoporosis Department of Chemistry, University of South Florida, Tampa, FL Jan 15, 2004.

9.       The Discovery and SAR of a Preclinical Candidate for the Treatment of Osteoporosis Department of Chemistry, University of Kentucky, Lexington, KY Dec 12, 2003.

10.    The Discovery and SAR of a Preclinical Candidate for the Treatment of Osteoporosis Department of Chemistry, University of Tennessee, Knoxville, TN Sept 4, 2003.

11.    The Synthesis and Preclinical Pharmacology of Prostaglandin Analogs for the Treatment of Glaucoma  Department of Ophthalmology, Duke University, Durham, NC; May 22, 2003.

12.    ‘Total Synthesis of Complex Products’ Session Chair 225th National ACS meeting, New Orleans, LA   March 27-31, 2003.

13.    ‘Avoiding Osmium’; Oxidative Cleavage Using Low Mol% Os.  Invited speaker International Conference on Oxidation and Reduction in Organic Chemistry, London, United Kingdom, Oct 28-30, 2002.

14.    The Discovery and SAR of a Preclinical Candidate for the Treatment of Osteoporosis  Department of Chemistry, Notre Dame University,  South Bend, IN April 2002.

15.    Asymmetric Synthesis Session Chair, 222nd National ACS meeting, Chicago, IL, August 26-30, 2001.

16.    The Discovery and SAR of a Preclinical Candidate for the Treatment of Osteoporosis Department of Chemistry, Wright State University Dayton, OH, Jan. 19, 2001.

17.    Asymmetric Synthesis Session Chair 221st National ACS meeting, San Diego, CA, April 1-5, 2001.

18.    The Discovery and SAR of a Preclinical Candidate for the Treatment of Osteoporosis Department of Chemistry, University of Georgia Athens, GA Dec. 7, 2000.

19.    The Discovery and SAR of a Preclinical Candidate for the Treatment of Osteoporosis   Department of Chemistry, Purdue University W. Lafayette, IN Nov. 7, 2000.

20.    General Organic Session Chair Midwest Regional ACS meeting, Covington, KY, May 12-15, 2000.

21.    FP Prostaglandins: Bone Anabolic Agents Department of Chemistry, Pennsylvania State University State College, PA Mar. 27, 2000.

22.    FP Prostaglandins: Their Use as Bone Anabolic Agents Department of Chemistry, ACTA, The Free University of Amsterdam Amsterdam, The Netherlands Feb. 24, 2000.

23.    FP Prostaglandins: Bone Anabolic Agents Department of Chemistry, Wayne State University Detroit, MI   Nov. 1999.

24.    Prostaglandins as Bone Anabolic Agents University of Amsterdam, Department of Chemistry, Amsterdam, The Netherlands, May 1999.

25.    Prostaglandins as Potential Bone Anabolic Agents Department of Chemistry, University of West Virginia Morgantown, WV Dec. 1998.

26.    Prostaglandins as Potential Bone Anabolic Agents Department of Chemistry, University of Cincinnati Cincinnati, OH Oct. 1998.

27.    The Synthesis of Natural Products and the First Synthesis of a trans-Fenestrane Department of Chemistry and Biochemistry, Duquesne University Pittsburgh, PA May 1998.

 

 

Graduate Level Classes Taught

Chemistry 761 University of Cincinnati; Advanced Physical Organic Chemistry 1994, 1996, 1998, 2000, 2003.

Chemistry 762 University of Cincinnati; Advanced Synthetic Organic Chemistry 1995, 1997, 1999, 2001, 2004.

Chemistry 763 University of Cincinnati; Advanced Organic Spectroscopy; 1995, 1997, 1999, 2001, 2004.

 

 

Crystal Structure Data (as yet unpublished paper)

 

CCDC 177946

Summary of Data CCDC 177946

Compound: 7-(2-(3-Benzo(b)thiophen-2-yl-3-hydroxy-propyl)-3,5-dihydroxy-cyclopentyl)-heptanoic acid

Unit cell parameters: a 45.623(6) b 5.9256(15) c 8.6481(7) beta 99.082(8)space group C2

 

 

Published Citations (other than to papers)

1.       Goard, M., Aakalu, G. Fedoryak, O. D., Quinonez, C., Julien, J.S.; Poteet, S.J., Schuman, E. M. Dore, T.M. Chemistry & Biology, Vol.12 685-693, June 2005

2.       www.albmolecular.com/features/ tekreps/vol10/no03/v10n03.pdf; Albany Molecular Research, Technical Reports, Vol. 10, No. 3, 2005. pp. 16-17.

3.       http://www.current-drugs.com/CDD/CDD/CDDPDF/issue%207/SW...Oct 2001

4.       Hopfinger, A. J. Wang, S.; Tokarski, J. S.; Jin, B. Q.; Albuquerque, M.; Madhav, P. J.; Duraiswami, C.  Construction Of 3D-QSAR Models of Prostaglandins Using The 4D-QSAR Analysis Formalism J. Am. Chem. Soc., 1997, 119, 10509.  (Cited for providing the data that was analyzed in the paper)

5.       Wulff, G. Chemische Berichte (1991) 124 (8), pp. 1885. (vid. Wulff, G., Wolf, G.  Chem. Ber. (1986), 119(6), 1876-89)

6.       Kane, B. J. Flavors and Fragrances International Meeting, August, 1988, Bombay, India

='margin-left:.5in;text-indent:-.25in;mso-list:l4 level1 lfo13; tab-stops:list .5in'>6.       Kane, B. J. Flavors and Fragrances International Meeting, August, 1988, Bombay, India