U.S. Department of Health and Human Services

Laboratory of Bioorganic Chemistry

Kenneth A. Jacobson, Ph.D., Chief

​Publications

A selection of recent and significant publications can be viewed below.

Publications
Zhao C, Hoppe T, Setty MK, Murray D, Chun TW, Hewlett I, Appella DH. Quantification of plasma HIV RNA using chemically engineered peptide nucleic acids. Nat Commun. 2014 Oct 6; 5 (2014 Oct 6; 5):5079. [Full Text/Abstract]
Ciruela F, Jacobson KA, Fernández-Dueñas V. Portraying g protein-coupled receptors with fluorescent ligands. ACS Chem Biol. 2014 Jul 28; 9 (2014 Jul 28; 9):1918-28. [Full Text/Abstract]
Englund EA, Gupta P, Micklitsch CM, Onyshchenko MI, Remeeva E, Neumann RD, Panyutin IG, Appella DH. PPG peptide nucleic acids that promote DNA guanine quadruplexes. Chembiochem. 2014 Jul 8; 15 (15; 13; 2014 Jul 8):1887-90. [Full Text/Abstract]
Dix AV, Moss SM, Phan K, Hoppe T, Paoletta S, Kozma E, Gao ZG, Durell SR, Jacobson KA, Appella DH. Programmable Nanoscaffolds That Control Ligand Display to a G-Protein-Coupled Receptor in Membranes To Allow Dissection of Multivalent Effects. J Am Chem Soc. 2014 Aug 25; 136 (35; 2014 Aug 25; 136):12296-303. [Full Text/Abstract]
Leung CT, Li A, Banerjee J, Gao ZG, Kambayashi T, Jacobson KA, Civan MM. The role of activated adenosine receptors in degranulation of human LAD2 mast cells. Purinergic Signal. 2014 Mar 5; 10 (2014 Mar 5; 10; 3):465-75. [Full Text/Abstract]
Vassilopoulos A, Xiao C, Chisholm C, Chen W, Xu X, Lahusen TJ, Bewley C, Deng CX. Synergistic Therapeutic Effect of Cisplatin and Phosphatidylinositol 3-Kinase (PI3K) Inhibitors in Cancer Growth and Metastasis of Brca1 Mutant Tumors. J Biol Chem. 2014 Jul 8; 289 (35; 289; 2014 Jul 8):24202-14. [Full Text/Abstract]
Gao ZG, Balasubramanian R, Kiselev E, Wei Q, Jacobson KA. Probing Biased/Partial Agonism at the G Protein-Coupled A2B Adenosine Receptoř. Biochem Pharmacol. 2014 Aug 1; 90 (2014 Aug 1; 3; 90):297-306. [Full Text/Abstract]
Toti KS, Moss SM, Paoletta S, Gao ZG, Jacobson KA, Van Calenbergh S. Synthesis and evaluation of N⁶-substituted apioadenosines as potential adenosine A₃ receptor modulators. Bioorg Med Chem. 2014 Aug 1; 22 (15; 2014 Aug 1; 22):4257-68. [Full Text/Abstract]
Tosh DK, Paoletta S, Chen Z, Moss SM, Gao ZG, Salvemini D, Jacobson KA. Extended N6 substitution of rigid C2-arylethynyl nucleosides for exploring the role of extracellular loops in ligand recognition at the A3 adenosine receptor. Bioorg Med Chem Lett. 2014 Aug 1; 24 (15; 2014 Aug 1; 24):3302-6. [Full Text/Abstract]
Ochoa-Cortes F, Liñán-Rico A, Jacobson KA, Christofi FL. Potential for Developing Purinergic Drugs for Gastrointestinal Diseases. Inflamm Bowel Dis. 2014 Jul; 20 (20; 7; 2014 Jul):1259-87. [Full Text/Abstract]
Kruse AC, Kobilka BK, Gautam D, Sexton PM, Christopoulos A, Wess J. Muscarinic acetylcholine receptors: novel opportunities for drug development. Nat Rev Drug Discov. 2014 Jul; 13 (7; 13; 2014 Jul):549-60. [Full Text/Abstract]
Procino G, Milano S, Carmosino M, Barbieri C, Nicoletti MC, Li JH, Wess J, Svelto M. Combination of secretin and fluvastatin ameliorates the polyuria associated with X-linked nephrogenic diabetes insipidus in mice. Kidney Int. 2014 Jul; 86 (86; 2014 Jul; 1):127-38. [Full Text/Abstract]
Byun NE, Grannan M, Bubser M, Barry RL, Thompson A, Rosanelli J, Gowrishankar R, Kelm ND, Damon S, Bridges TM, Melancon BJ, Tarr JC, Brogan JT, Avison MJ, Deutch AY, Wess J, Wood MR, Lindsley CW, Gore JC, Conn PJ, Jones CK. Antipsychotic Drug-Like Effects of the Selective M4 Muscarinic Acetylcholine Receptor Positive Allosteric Modulator VU0152100. Neuropsychopharmacology. 2014 Jun; 39 (39; 7; 2014 Jun):1578-93. [Full Text/Abstract]
Kruse AC, Hu J, Kobilka BK, Wess J. Muscarinic acetylcholine receptor X-ray structures: potential implications for drug development. Curr Opin Pharmacol. 2014 Jun; 16 (16; 2014 Jun):24-30. [Full Text/Abstract]
Nichols JL, Gladwell W, Verhein KC, Cho HY, Wess J, Suzuki O, Wiltshire T, Kleeberger SR. Genome-wide association mapping of acute lung injury in neonatal inbred mice. FASEB J. 2014 Jun; 28 (28; 6; 2014 Jun):2538-50. [Full Text/Abstract]
Chen SR, Chen H, Yuan WX, Wess J, Pan HL. Differential regulation of primary afferent input to spinal cord by muscarinic receptor subtypes delineated using knockout mice. J Biol Chem. 2014 May 16; 289 (20; 289; 2014 May 16):14321-30. [Full Text/Abstract]
Jayasekara PS, Barrett MO, Ball CB, Brown KA, Hammes E, Balasubramanian R, Harden TK, Jacobson KA. 4-Alkyloxyimino Derivatives of Uridine-5'-triphosphate: Distal Modification of Potent Agonists as a Strategy for Molecular Probes of P2Y2, P2Y4, and P2Y6 Receptors. J Med Chem. 2014 May 8; 57 (9; 2014 May 8; 57):3874-83. [Full Text/Abstract]
Zhang K, Zhang J, Gao ZG, Zhang D, Zhu L, Han GW, Moss SM, Paoletta S, Kiselev E, Lu W, Fenalti G, Zhang W, Müller CE, Yang H, Jiang H, Cherezov V, Katritch V, Jacobson KA, Stevens RC, Wu B, Zhao Q. Structure of the human P2Y12 receptor in complex with an antithrombotic drug. Nature. 2014 May 1; 509 (2014 May 1; 509; 7498):115-8. [Full Text/Abstract]
Yang T, Shen JB, Yang R, Redden J, Dodge-Kafka K, Grady J, Jacobson KA, Liang BT. A Novel Protective Role of Endogenous Cardiac Myocyte P2X4 Receptors in Heart Failure. Circ Heart Fail. 2014 May; 7 (7; 2014 May; 3):510-8. [Full Text/Abstract]
Zhang J, Zhang K, Gao ZG, Paoletta S, Zhang D, Han GW, Li T, Ma L, Zhang W, Müller CE, Yang H, Jiang H, Cherezov V, Katritch V, Jacobson KA, Stevens RC, Wu B, Zhao Q. Agonist-bound structure of the human P2Y12 receptor. Nature. 2014 May 1; 509 (2014 May 1; 509; 7498):119-122. [Full Text/Abstract]
Uddin T, Aktar A, Xu P, Johnson RA, Rahman MA, Leung DT, Afrin S, Akter A, Alam MM, Rahman A, Chowdhury F, Khan AI, Bhuiyan TR, Bufano MK, Rashu R, Yu Y, Wu-Freeman Y, Harris JB, Larocque RC, Charles RC, Kovač P, Calderwood SB, Ryan ET, Qadri F. Immune Responses to O-Specific Polysaccharide and Lipopolysaccharide of Vibrio cholerae O1 Ogawa in Adult Bangladeshi Recipients of an Oral Killed Cholera Vaccine and Comparison to Responses in Patients with Cholera. Am J Trop Med Hyg. 2014 May; 90 (2014 May; 5; 90):873-81. [Full Text/Abstract]
Charles RC, Hilaire IJ, Mayo-Smith LM, Teng JE, Jerome JG, Franke MF, Saha A, Yu Y, Kováč P, Calderwood SB, Ryan ET, Larocque RC, Almazor CP, Qadri F, Ivers LC, Harris JB. Immunogenicity of a Killed Bivalent (O1 and O139) Whole Cell Oral Cholera Vaccine, Shanchol, in Haiti. PLoS Negl Trop Dis. 2014 May; 8 (8; 2014 May; 5):e2828. [Full Text/Abstract]
Nayak A, Chandra G, Hwang I, Kim K, Hou X, Kim HO, Sahu PK, Roy KK, Yoo J, Lee Y, Cui M, Choi S, Moss SM, Phan K, Gao ZG, Ha H, Jacobson KA, Jeong LS. Synthesis and anti-renal fibrosis activity of conformationally locked truncated 2-hexynyl-N(6)-substituted-(N)-methanocarba-nucleosides as A3 adenosine receptor antagonists and partial agonists. J Med Chem. 2014 Feb 27; 57 (4; 2014 Feb 27; 57):1344-54. [Full Text/Abstract]
Alam MM, Bufano MK, Xu P, Kalsy A, Yu Y, Freeman YW, Sultana T, Rashu MR, Desai I, Eckhoff G, Leung DT, Charles RC, LaRocque RC, Harris JB, Clements JD, Calderwood SB, Qadri F, Vann WF, Kováč P, Ryan ET. Evaluation in mice of a conjugate vaccine for cholera made from Vibrio cholerae O1 (Ogawa) O-specific polysaccharide. PLoS Negl Trop Dis. 2014 Feb; 8 (8; 2; 2014 Feb):e2683. [Full Text/Abstract]
Gericke A, Steege A, Manicam C, Böhmer T, Wess J, Pfeiffer N. Role of the M3 muscarinic acetylcholine receptor subtype in murine ophthalmic arteries after endothelial removal. Invest Ophthalmol Vis Sci. 2014 Jan 29; 55 (2014 Jan 29; 55; 1):625-31. [Full Text/Abstract]
Englund EA, Zhang N, Appella DH. Cyclopentane peptide nucleic acids. Methods Mol Biol. 2014; 1050 (2014; 1050):13-8. [Full Text/Abstract]
Soliman, S. E.; Kovac, P. Practical Synthesis of Building Blocks for Oligosaccharides Containing the β-D-Galp-(1→3)-β-D-GlcpNAc Motif. Synthesis. 2014; 46 (46; 2014):748-751. [Full Text/Abstract]
Jacobson KA. Crystal structures of the A2A adenosine receptor and their use in medicinal chemistry. In Silico Pharmacol. 2013 Dec 20; 1 (2013 Dec 20; 1):22. [Full Text/Abstract]
Jahouh F, Xu P, Vann WF, Kováč P, Banoub JH. Mapping the glycation sites in the neoglycoconjugate from hexasaccharide antigen of Vibrio cholerae, serotype Ogawa and the recombinant tetanus toxin C-fragment carrier. J Mass Spectrom. 2013 Oct; 48 (2013 Oct; 48; 10):1083-90. [Full Text/Abstract]
Leung DT, Uddin T, Xu P, Aktar A, Johnson RA, Rahman MA, Alam MM, Bufano MK, Eckhoff G, Wu-Freeman Y, Yu Y, Sultana T, Khanam F, Saha A, Chowdhury F, Khan AI, Charles RC, Larocque RC, Harris JB, Calderwood SB, Kovác P, Qadri F, Ryan ET. Immune responses to the O-specific polysaccharide antigen in children who received a killed oral cholera vaccine compared to responses following natural cholera infection in Bangladesh. Clin Vaccine Immunol. 2013 Jun; 20 (20; 6; 2013 Jun):780-8. [Full Text/Abstract]
Jain S, Ruiz de Azua I, Lu H, White MF, Guettier JM, Wess J. Chronic activation of a designer G(q)-coupled receptor improves β cell function. J Clin Invest. 2013 Apr 1; 123 (2013 Apr 1; 123; 4):1750-62. [Full Text/Abstract]
Arteaga-Solis E, Zee T, Emala CW, Vinson C, Wess J, Karsenty G. Inhibition of leptin regulation of parasympathetic signaling as a cause of extreme body weight-associated asthma. Cell Metab. 2013 Jan 8; 17 (17; 1; 2013 Jan 8):35-48. [Full Text/Abstract]
Micklitsch CM, Oquare BY, Zhao C, Appella DH. Cyclopentane-peptide nucleic acids for qualitative, quantitative, and repetitive detection of nucleic acids. Anal Chem. 2013 Jan 2; 85 (85; 2013 Jan 2; 1):251-7. [Full Text/Abstract]
Lu, X.; Sail, D.; Kovac, P. 6-O-Benzylidene and 4,6-O-methoxybenzylidene a,b-cellobiose and their hexa-O-benzoyl derivatives. Synthesis. 2013; 45 (45; 2013):1946-1949. [Full Text/Abstract]
Johnson RA, Uddin T, Aktar A, Mohasin M, Alam MM, Chowdhury F, Harris JB, LaRocque RC, Bufano MK, Yu Y, Wu-Freeman Y, Leung DT, Sarracino D, Krastins B, Charles RC, Xu P, Kovác P, Calderwood SB, Qadri F, Ryan ET. Comparison of immune responses to the O-specific polysaccharide and lipopolysaccharide of Vibrio cholerae O1 in Bangladeshi adult patients with cholera. Clin Vaccine Immunol. 2012 Nov; 19 (19; 2012 Nov; 11):1712-21. [Full Text/Abstract]
Tosh DK, Paoletta S, Deflorian F, Phan K, Moss SM, Gao ZG, Jiang X, Jacobson KA. Structural sweet spot for A1 adenosine receptor activation by truncated (N)-methanocarba nucleosides: receptor docking and potent anticonvulsant activity. J Med Chem. 2012 Sep 27; 55 (2012 Sep 27; 55; 18):8075-90. [Full Text/Abstract]
Jacobson KA, Costanzi S. New insights for drug design from the X-ray crystallographic structures of G-protein-coupled receptors. Mol Pharmacol. 2012 Sep; 82 (2012 Sep; 82; 3):361-71. [Full Text/Abstract]
Shahzad-ul-Hussan S, Ghirlando R, Dogo-Isonagie CI, Igarashi Y, Balzarini J, Bewley CA. Characterization and carbohydrate specificity of pradimicin S. J Am Chem Soc. 2012 Aug 1; 134 (30; 2012 Aug 1; 134):12346-9. [Full Text/Abstract]
Jahouh F, Saksena R, Kováč P, Banoub J. Revealing the glycation sites in synthetic neoglycoconjugates formed by conjugation of the antigenic monosaccharide hapten of Vibrio cholerae O1, serotype Ogawa with the BSA protein carrier using LC-ESI-QqTOF-MS/MS. J Mass Spectrom. 2012 Jul; 47 (7; 2012 Jul; 47):890-900. [Full Text/Abstract]
Tosh DK, Phan K, Gao ZG, Gakh AA, Xu F, Deflorian F, Abagyan R, Stevens RC, Jacobson KA, Katritch V. Optimization of adenosine 5'-carboxamide derivatives as adenosine receptor agonists using structure-based ligand design and fragment screening. J Med Chem. 2012 May 10; 55 (55; 9; 2012 May 10):4297-308. [Full Text/Abstract]
Chen Z, Janes K, Chen C, Doyle T, Bryant L, Tosh DK, Jacobson KA, Salvemini D. Controlling murine and rat chronic pain through A3 adenosine receptor activation. FASEB J. 2012 May; 26 (2012 May; 5; 26):1855-65. [Full Text/Abstract]
Dogo-Isonagie C, Lam S, Gustchina E, Acharya P, Yang Y, Shahzad-ul-Hussan S, Clore GM, Kwong PD, Bewley CA. Peptides from second extracellular loop of C-C chemokine receptor type 5 (CCR5) inhibit diverse strains of HIV-1. J Biol Chem. 2012 Apr 27; 287 (287; 2012 Apr 27; 18):15076-86. [Full Text/Abstract]
Jahouh F, Hou SJ, Kováč P, Banoub JH. Determination of glycation sites by tandem mass spectrometry in a synthetic lactose-bovine serum albumin conjugate, a vaccine model prepared by dialkyl squarate chemistry. Rapid Commun Mass Spectrom. 2012 Apr 15; 26 (7; 2012 Apr 15; 26):749-58. [Full Text/Abstract]
Tarique AA, Kalsy A, Arifuzzaman M, Rollins SM, Charles RC, Leung DT, Harris JB, Larocque RC, Sheikh A, Bhuiyan MS, Saksena R, Clements JD, Calderwood SB, Qadri F, Kovác P, Ryan ET. Transcutaneous immunization with a Vibrio cholerae O1 Ogawa synthetic hexasaccharide conjugate following oral whole-cell cholera vaccination boosts vibriocidal responses and induces protective immunity in mice. Clin Vaccine Immunol. 2012 Apr; 19 (19; 4; 2012 Apr):594-602. [Full Text/Abstract]
Fishman P, Bar-Yehuda S, Liang BT, Jacobson KA. Pharmacological and therapeutic effects of A3 adenosine receptor agonists. Drug Discov Today. 2012 Apr; 17 (17; 2012 Apr; 7-8):359-66. [Full Text/Abstract]
Kumar S, Kellish P, Robinson WE Jr, Wang D, Appella DH, Arya DP. Click dimers to target HIV TAR RNA conformation. Biochemistry. 2012 Mar 20; 51 (2012 Mar 20; 51; 11):2331-47. [Full Text/Abstract]
Kruse AC, Hu J, Pan AC, Arlow DH, Rosenbaum DM, Rosemond E, Green HF, Liu T, Chae PS, Dror RO, Shaw DE, Weis WI, Wess J, Kobilka BK. Structure and dynamics of the M3 muscarinic acetylcholine receptor. Nature. 2012 Feb 22; 482 (2012 Feb 22; 482; 7386):552-6. [Full Text/Abstract]
Hu J, Thor D, Zhou Y, Liu T, Wang Y, McMillin SM, Mistry R, Challiss RA, Costanzi S, Wess J. Structural aspects of M₃ muscarinic acetylcholine receptor dimer formation and activation. FASEB J. 2012 Feb; 26 (2012 Feb; 2; 26):604-16. [Full Text/Abstract]
Englund EA, Wang D, Fujigaki H, Sakai H, Micklitsch CM, Ghirlando R, Martin-Manso G, Pendrak ML, Roberts DD, Durell SR, Appella DH. Programmable multivalent display of receptor ligands using peptide nucleic acid nanoscaffolds. Nat Commun. 2012 Jan 10; 3 (2012 Jan 10; 3):614. [Full Text/Abstract]
Panyutin IG, Onyshchenko MI, Englund EA, Appella DH, Neumann RD. Targeting DNA G-quadruplex structures with peptide nucleic acids. Curr Pharm Des. 2012; 18 (2012; 14; 18):1984-91. [Full Text/Abstract]