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Molecular and Cellular Biosciences at Wake Forest University


Wake Forest University Graduate School » Molecular and Cellular Biosciences

Paul Brandon Jones, Ph.D.

Paul Brandon Jones, Ph.D.

Associate Professor

B.S. 1993, Oklahoma State University
Ph.D. 1998, Duke University
Postdoctoral Research Associate 1998-2000,
The Johns Hopkins University

 

Jones' Group Publications

17.Sarma, S.J.; Jones, P.B. "Photochemistry of 1,n-Dibenzyloxy-9,10-anthraquinones."  J. Org. Chem. 2010,  75, 3806-3813.

16.Elkazaz, S.; Jones, P.B. "Photochemical hydroxylation of 1-methyl-9,10-anthraquinones; synthesis of 9'-hydroxyaloesaponarin II." J. Org. Chem.201075, 412-416.

15.Brinson, R.G.; Sarma, S.; Elkazaz, S.; Jones, P.B. "Observation of Heavy Atom Effects in the Development of Water Soluble Caged 4-hydroxy-trans-2-nonenal." Org. Biomol. Chem. 2008 6 4204-4211.

14.Oates, R.P.; Jones, P.B. "Photosensitized Tetrahydropyran Transfer." J. Org. Chem.200873, 4743-4745.

13.Oshige, E.S.; Jones, P.B.   "Photoactivated artificial metalloesterases."    J. Photochem. Photobiol., A: Chem.  2007,  192,  142-151. 

12.Zuidema, D.R.; Jones, P.B. "Triplet Photosensitization in Cyercene A and Related Pyrones." J. Photochem. Photobiol. B: Biology200683, 137-145.

11.Zuidema, D.R.; Miller, A.K.; Trauner, D.; Jones, P.B. “Photosensitized Conversion of 9,10-Deoxytridachione to Photodeoxytridachione.” Org. Lett. 20057, 4959-4962.

10.Harrison, B.; Czerw, R.; Konchady, M.S.; Pai, D.M.; Lopatka, M.W.*; Jones, P.B. “Ionic Liquids Incorporating Nanomaterials as Lubricants for Harsh Environments.” Proc. ASME Materials Division, 2005. 100, 405-410.

9.Hubbard, S.C.; Jones, P.B. "Ionic-Liquid Soluble hotosensitizers." Tetrahedron 2005,61, 7425-7430.

8.Brinson, R.G.; Hubbard, S.C.; Zuidema, D.R.; Jones, P.B. “Two New Anthraquinone Photoreactions.” J. Photochem. Photobiol. A. Chemistry. 2005175, 118-128.

7.Zuidema, D.R.; Jones, P.B. "Photochemical Relationships in Sacoglossan Polypropionates." J. Nat. Prod. 200568, 481-486.

6.Brinson, R.G.; Jones, P.B. "Caged trans-4-hydroxy-2-nonenal." Organic Letters 2004,6, 3767-3770.

5.Glenn, A.G.; Jones, P.B. “ Thermal Stability of Ionic Liquid BMI(BF4) in the Presence of Nucleophiles.” Tetrahedron Lett. 200445, 6967-6969.

4.Brinson, R.G.; Jones, P.B. “ N-Allyl-1,3-oxazines via a Facile Keto-ene/cyclization Tandem Reaction.” Tetrahedron Lett. 2004, 45, 6155-6158.

3.Reynolds, J.D.; Brinson, R.G.; Day, C.S.; Jones, P.B. "Highly Strained Dihydroanthraquinones: Oxidation vs. Elimination." Tetrahedron Lett. 200445, 2955-2959.

2.Jones, P.B.; Reynolds, J.L.; Brinson, R.G.; Butke, R.A., "Amine Mediated Photoreduction of Aryl Ketones in N-Heterocyclic Ionic Liquids." ACS Symposium Series: Ionic Liquids as Green Solvents: Progress and Prospects. 2003856, 370-380.

1.Reynolds, J.L.; Erdner, K.R.; Jones, P.B. "Photoreduction of Benzophenones by Amines in Room Temperature Ionic Liquids." Organic Letters 20024917-919.   

PBJ Publications with Craig Townsend

1.Jones, P.B.; Parrish, N.M.; Houston, T.A.; Stapon, A.; Bansal, N.P.; Dick, J.D.; Townsend, C.A. "A New Class of Anti-Tuberculosis Agents.” J. Med. Chem.200043, 3304-3314.

2.Parrish, N.P.; Houston, T.A.; Jones, P.B.; Townsend, C.A.; Dick, J.D. "In-Vitro Activity of a Novel Anti-Mycobacterial Compound, N-Octane Sulfonyl Acetamide, and its Effects on Lipid and Mycolic Acid Synthesis." Antimicrob. Agents Chem., 200145,1143-1150.

3.Parrish N.M.; Ko C.G.; Dick J.D.; Jones P.B.; Ellingson J.L.E.   "Growth, Congo Red agar colony morphotypes and antibiotic susceptibility testing of Mycobacterium aviumsubspecies   paratuberculosis."    Clin. Med. Res. 2004,  2,  107-14.

PBJ Publications with Ned Porter

1.Jones, P.B.; Pollastri, M.P.; Porter, N.A. “2-Benzoylbenzoic Acid: A Photolabile Mask for Alcohols and Thiols.” J. Org. Chem.1996,61, 9455-9461.

2.Arroyo, J.G.; Jones, P.B.; Porter, N.A.; Hatchell, D.L. “In-Vivo Photoactivation of Caged-Thrombin.” Thrombosis & Haemostasis199778(2), 791-793.3.Jones, P.B.; Porter, N.A. “2-Aroyl Benzoyl Serine Proteases: Photoreversible Inhibition or Photoaffinity Labeling?” J. Am. Chem. Soc. , 1999121, 2753-2761.   

PBJ Publications with Richard Bunce

1.Bunce, R.A.; Peeples, C.J.; Jones, P.B. “Tandem S N2-Michael Reactions for the Preparation of Simple 5-Membered and 6-Membered Ring Nitrogen and Sulfur Heterocycles." J. Org. Chem., 199257, 1727-1733.

2.Bunce, R.A.; Dowdy, E.D.; Jones, P.B.; Holt, E.M. “Functionalized Carbocycles by Tandem Dealkoxycarboxylation-Michael Addition Reactions.” J. Org. Chem., 199358, 7143-7148.

3.Bunce, R.A.; Dowdy, E.D.; Childress, S.; Jones, P.B. “2,2,3-Trisubstituted Tetrahydrofurans and 2H-Tetrahydrofurans by Tandem Demethoxycarbonylation-Michael Addition Reactions.” J. Org. Chem., 199863, 144-151.   

PBJ Publications outside of chemistry

1.Jones, P.B. "Globular Treasures Near Summer Showpieces." Sky and Telescope2003,9, 111-116.

2.Jones, P.B. “Marathons.” Amateur Astronomy200441, 28-31.

3.Jones, P.B. "Thy Neighbor's Scope." Sky and Telescope20057, 142.

4.Jones, P.B. “Observe Shallow-Space Objects.” Chapter 23, pp 145-152, in Astronomy Hacks by Robert B. Thompson. O’Reilly Media Inc., Sebastopol, CA, 2005.

5.Jones, P.B. “Slow Down, You Move Too Fast, You’ve Got to Make the Evening Last.” Chapter 24, pp 153-160, in Astronomy Hacks by Robert B. Thompson. O’Reilly Media Inc., Sebastopol, CA, 2005.

6.Jones, P.B. “Photograph the Stars with Basic Equipment.” Chapter 31, pp 197-202, in Astronomy Hacks by Robert B. Thompson. O’Reilly Media Inc., Sebastopol, CA, 2005.

 

 

Research Summary

I am interested in studying how photochemistry is used in nature and in developing photochemical methods to generate synthetically and medically significant products. Because most organisms depend directly on photochemical processes for their survival, photochemistry is essential to life on earth. The chemistry of photosynthesis and vision are the best examples of this, but many species have more subtle life processes (e.g. circadian rhythms) that rely on photochemistry. In nature, photochemical pathways are well regulated and, like most biochemical pathways, generate specific products. In the laboratory, however, photochemical reactions often yield a variety of products with little or no regio- or stereoselectivity. Specificity in photochemical reactions is achieved in biochemical systems by steric and electronic control of the chromophore and of the molecules with which the excited chromophore interacts. Using these systems as a model, I intend to study how photochemistry can be used to control biological systems and how structure and reaction conditions can be used to direct photochemical reaction pathways. Several projects are summarized below.

1. Photochemistry in Ionic Liquids Room temperature ionic liquids (RTILs) are salts that freeze below 25oC. Though such salts have been known for almost a century, they have recently gained popularity as “green” alternatives to conventional solvents. RTILs are generally immiscible with water and many organic solvents so that products and by-products can be easily removed via extraction. The ease of product removal allows easy re-use of the solvent. This property, coupled with an extremely low vapor pressure, makes RTILs much less environmentally intrusive than conventional solvents. A number of reactions have been shown to be compatible with ionic liquids, including: Diels-Alder cycloadditions, alkene halogenations, Stille couplings, and hydrogenation reactions. Investigations of reactions in RTILs continues to be an area of increasing activity.We became interested in studying how these unique solvents might affect photochemical reaction pathways. Because RTILs are highly conductive, we speculate that radical pairs formed in such solvents may undergo electron transfer to produce ion pairs. This type of radical pair – ion pair equilibrium has been described by Arnett. Our efforts in this area are know focussing on the amine mediated photoreduction of aryl ketones in a variety of RTILs.

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2. Photoregulation of Biologically Active Molecules.
Over the past twenty years, technology for photoregulation of enzyme activity has been developed. This technology has been applied to the development of simple, artificial photosynthetic systems and to the in vivo clotting of blood. For therapeutic applications, however, these photoregulation systems suffer from several disadvantages. Two elements key to any enzyme photoregulation system that is to be used in vivo are: 1) complete enzyme inhibition prior to irradiation and 2) photoactivation with light that is benign to living tissue. One goal is to create an enzyme photoregulation strategy that combines both of these elements. I intend to pursue several strategies that utilize photoinduced electron transfer to appropriately substituted polyaromatic compounds while also serving as the enzyme inhibitor by covalently modifying the lysine amino groups on the enzyme surface. The ultimate goal of this project, however, is the development of chemistry that allows the delivery of a chemotherapeutic agent specifically to the desired location. This has the potential of greatly easing side effects in the treatment of ailments where the affected tissue is accessible to light sources, such as cancers of the throat, skin, and bladder, and disorders involving the eye.

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In the example, an enzyme is inactivated by modification with a large blocking group – in this case, a saccharide conjugated to a protein – of the lysine groups on the enzyme outer surface. The blocking group carries a chromophore capable of photooxidizing the amino group to an imine. The imine will be readily hydrolyzed to give a lactone and free (active) enzyme.