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Items: 46


Therapeutic efficacy of LN-1-255 in combination with imipenem in severe infection caused by carbapenem-resistant Acinetobacter baumannii.

Vázquez-Ucha JC, Martínez-Guitián M, Maneiro M, Conde-Pérez K, Álvarez-Fraga L, Torrens G, Oliver A, Buynak JD, Bonomo RA, Bou G, González-Bello C, Poza M, Beceiro A.

Antimicrob Agents Chemother. 2019 Aug 5. pii: AAC.01092-19. doi: 10.1128/AAC.01092-19. [Epub ahead of print]


Virtual Screening and Experimental Testing of B1 Metallo-β-lactamase Inhibitors.

Kang JS, Zhang AL, Faheem M, Zhang CJ, Ai N, Buynak JD, Welsh WJ, Oelschlaeger P.

J Chem Inf Model. 2018 Sep 24;58(9):1902-1914. doi: 10.1021/acs.jcim.8b00133. Epub 2018 Aug 29.


Functionalizing the γ-Position of α-Diazo-β-ketoesters.

Nguyen TQ, Alqurafi M, Edwards C, Nguyen P, Kim J, Casco S, Bennet M, Chiang C, Lohry M, Cox M, Meshram B, Le D, Kim E, Smriti S, Oelschlaeger P, Buynak JD.

Tetrahedron Lett. 2016 Jun 27;57(30):3330-3333. Epub 2016 Jun 16.


LN-1-255, a penicillanic acid sulfone able to inhibit the class D carbapenemase OXA-48.

Vallejo JA, Martínez-Guitián M, Vázquez-Ucha JC, González-Bello C, Poza M, Buynak JD, Bethel CR, Bonomo RA, Bou G, Beceiro A.

J Antimicrob Chemother. 2016 Aug;71(8):2171-80. doi: 10.1093/jac/dkw105. Epub 2016 Apr 28.


Triethysilyl Enol Ethers in the Synthesis of Carbapenem Precursors.

Nguyen TQ, Chai W, Gu J, Cook K, Kim E, Goetz S, Farni Z, Chepuru M, Cox M, Nguyen P, Raja H, Magistrado P, Michael F, Oelschlaeger P, Buynak JD.

Tetrahedron Lett. 2015 Jun 3;56(23):3385-3389.


Meropenem and chromacef intermediates observed in IMP-25 metallo-β-lactamase-catalyzed hydrolysis.

Oelschlaeger P, Aitha M, Yang H, Kang JS, Zhang AL, Liu EM, Buynak JD, Crowder MW.

Antimicrob Agents Chemother. 2015 Jul;59(7):4326-30. doi: 10.1128/AAC.04409-14. Epub 2015 Apr 27.


Detecting a quasi-stable imine species on the reaction pathway of SHV-1 β-lactamase and 6β-(hydroxymethyl)penicillanic acid sulfone.

Che T, Rodkey EA, Bethel CR, Shanmugam S, Ding Z, Pusztai-Carey M, Nottingham M, Chai W, Buynak JD, Bonomo RA, van den Akker F, Carey PR.

Biochemistry. 2015 Jan 27;54(3):734-43. doi: 10.1021/bi501197t. Epub 2015 Jan 8.


Penam sulfones and β-lactamase inhibition: SA2-13 and the importance of the C2 side chain length and composition.

Rodkey EA, Winkler ML, Bethel CR, Pagadala SR, Buynak JD, Bonomo RA, van den Akker F.

PLoS One. 2014 Jan 16;9(1):e85892. doi: 10.1371/journal.pone.0085892. eCollection 2014.


β-Lactamase inhibition by 7-alkylidenecephalosporin sulfones: allylic transposition and formation of an unprecedented stabilized acyl-enzyme.

Rodkey EA, McLeod DC, Bethel CR, Smith KM, Xu Y, Chai W, Che T, Carey PR, Bonomo RA, van den Akker F, Buynak JD.

J Am Chem Soc. 2013 Dec 11;135(49):18358-69. doi: 10.1021/ja403598g. Epub 2013 Dec 3.


β-Lactamase inhibitors: a review of the patent literature (2010 - 2013).

Buynak JD.

Expert Opin Ther Pat. 2013 Nov;23(11):1469-81. doi: 10.1517/13543776.2013.831071. Epub 2013 Aug 23. Review.


Structures of SHV-1 β-lactamase with penem and penam sulfone inhibitors that form cyclic intermediates stabilized by carbonyl conjugation.

Ke W, Pattanaik P, Bethel CR, Sheri A, Buynak JD, Bonomo RA, van den Akker F.

PLoS One. 2012;7(11):e49035. doi: 10.1371/journal.pone.0049035. Epub 2012 Nov 8.


Early insights into the interactions of different β-lactam antibiotics and β-lactamase inhibitors against soluble forms of Acinetobacter baumannii PBP1a and Acinetobacter sp. PBP3.

Papp-Wallace KM, Senkfor B, Gatta J, Chai W, Taracila MA, Shanmugasundaram V, Han S, Zaniewski RP, Lacey BM, Tomaras AP, Skalweit MJ, Harris ME, Rice LB, Buynak JD, Bonomo RA.

Antimicrob Agents Chemother. 2012 Nov;56(11):5687-92. doi: 10.1128/AAC.01027-12. Epub 2012 Aug 20.


Carboxylation and decarboxylation of active site Lys 84 controls the activity of OXA-24 β-lactamase of Acinetobacter baumannii: Raman crystallographic and solution evidence.

Che T, Bonomo RA, Shanmugam S, Bethel CR, Pusztai-Carey M, Buynak JD, Carey PR.

J Am Chem Soc. 2012 Jul 11;134(27):11206-15. doi: 10.1021/ja303168n. Epub 2012 Jun 28.


The importance of the trans-enamine intermediate as a β-lactamase inhibition strategy probed in inhibitor-resistant SHV β-lactamase variants.

Ke W, Rodkey EA, Sampson JM, Skalweit MJ, Sheri A, Pagadala SR, Nottingham MD, Buynak JD, Bonomo RA, van den Akker F.

ChemMedChem. 2012 Jun;7(6):1002-8. doi: 10.1002/cmdc.201200006. Epub 2012 Mar 21.


Crystal structures of KPC-2 β-lactamase in complex with 3-nitrophenyl boronic acid and the penam sulfone PSR-3-226.

Ke W, Bethel CR, Papp-Wallace KM, Pagadala SR, Nottingham M, Fernandez D, Buynak JD, Bonomo RA, van den Akker F.

Antimicrob Agents Chemother. 2012 May;56(5):2713-8. doi: 10.1128/AAC.06099-11. Epub 2012 Feb 13.


Inactivation of a class A and a class C β-lactamase by 6β-(hydroxymethyl)penicillanic acid sulfone.

Papp-Wallace KM, Bethel CR, Gootz TD, Shang W, Stroh J, Lau W, McLeod D, Price L, Marfat A, Distler A, Drawz SM, Chen H, Harry E, Nottingham M, Carey PR, Buynak JD, Bonomo RA.

Biochem Pharmacol. 2012 Feb 15;83(4):462-71. doi: 10.1016/j.bcp.2011.11.015. Epub 2011 Dec 2.


Ligand-dependent disorder of the Omega loop observed in extended-spectrum SHV-type beta-lactamase.

Sampson JM, Ke W, Bethel CR, Pagadala SR, Nottingham MD, Bonomo RA, Buynak JD, van den Akker F.

Antimicrob Agents Chemother. 2011 May;55(5):2303-9. doi: 10.1128/AAC.01360-10. Epub 2011 Feb 28.


Modifications of the C6-substituent of penicillin sulfones with the goal of improving inhibitor recognition and efficacy.

Nottingham M, Bethel CR, Pagadala SR, Harry E, Pinto A, Lemons ZA, Drawz SM, Akker Fv, Carey PR, Bonomo RA, Buynak JD.

Bioorg Med Chem Lett. 2011 Jan 1;21(1):387-93. doi: 10.1016/j.bmcl.2010.10.134. Epub 2010 Nov 5.


Design, synthesis, and crystal structures of 6-alkylidene-2'-substituted penicillanic acid sulfones as potent inhibitors of Acinetobacter baumannii OXA-24 carbapenemase.

Bou G, Santillana E, Sheri A, Beceiro A, Sampson JM, Kalp M, Bethel CR, Distler AM, Drawz SM, Pagadala SR, van den Akker F, Bonomo RA, Romero A, Buynak JD.

J Am Chem Soc. 2010 Sep 29;132(38):13320-31. doi: 10.1021/ja104092z.


Penicillin sulfone inhibitors of class D beta-lactamases.

Drawz SM, Bethel CR, Doppalapudi VR, Sheri A, Pagadala SR, Hujer AM, Skalweit MJ, Anderson VE, Chen SG, Buynak JD, Bonomo RA.

Antimicrob Agents Chemother. 2010 Apr;54(4):1414-24. doi: 10.1128/AAC.00743-09. Epub 2010 Jan 19.


Role of E166 in the imine to enamine tautomerization of the clinical beta-lactamase inhibitor sulbactam.

Kalp M, Buynak JD, Carey PR.

Biochemistry. 2009 Nov 3;48(43):10196-8. doi: 10.1021/bi901416t.


Approaches to the simultaneous inactivation of metallo- and serine-beta-lactamases.

Ganta SR, Perumal S, Pagadala SR, Samuelsen O, Spencer J, Pratt RF, Buynak JD.

Bioorg Med Chem Lett. 2009 Mar 15;19(6):1618-22. doi: 10.1016/j.bmcl.2009.02.018. Epub 2009 Feb 8.


Strategic design of an effective beta-lactamase inhibitor: LN-1-255, a 6-alkylidene-2'-substituted penicillin sulfone.

Pattanaik P, Bethel CR, Hujer AM, Hujer KM, Distler AM, Taracila M, Anderson VE, Fritsche TR, Jones RN, Pagadala SR, van den Akker F, Buynak JD, Bonomo RA.

J Biol Chem. 2009 Jan 9;284(2):945-53. doi: 10.1074/jbc.M806833200. Epub 2008 Oct 27.


Sulbactam forms only minimal amounts of irreversible acrylate-enzyme with SHV-1 beta-lactamase.

Totir MA, Helfand MS, Carey MP, Sheri A, Buynak JD, Bonomo RA, Carey PR.

Biochemistry. 2007 Aug 7;46(31):8980-7. Epub 2007 Jul 13.


Raman crystallographic studies of the intermediates formed by Ser130Gly SHV, a beta-lactamase that confers resistance to clinical inhibitors.

Helfand MS, Taracila MA, Totir MA, Bonomo RA, Buynak JD, van den Akker F, Carey PR.

Biochemistry. 2007 Jul 24;46(29):8689-99. Epub 2007 Jun 27.


Efficient inhibition of class A and class D beta-lactamases by Michaelis complexes.

Kalp M, Sheri A, Buynak JD, Bethel CR, Bonomo RA, Carey PR.

J Biol Chem. 2007 Jul 27;282(30):21588-91. Epub 2007 Jun 8.


Rational design of a beta-lactamase inhibitor achieved via stabilization of the trans-enamine intermediate: 1.28 A crystal structure of wt SHV-1 complex with a penam sulfone.

Padayatti PS, Sheri A, Totir MA, Helfand MS, Carey MP, Anderson VE, Carey PR, Bethel CR, Bonomo RA, Buynak JD, van den Akker F.

J Am Chem Soc. 2006 Oct 11;128(40):13235-42.


Understanding the longevity of the beta-lactam antibiotics and of antibiotic/beta-lactamase inhibitor combinations.

Buynak JD.

Biochem Pharmacol. 2006 Mar 30;71(7):930-40. Epub 2005 Dec 13. Review.


Clavulanic acid inactivation of SHV-1 and the inhibitor-resistant S130G SHV-1 beta-lactamase. Insights into the mechanism of inhibition.

Sulton D, Pagan-Rodriguez D, Zhou X, Liu Y, Hujer AM, Bethel CR, Helfand MS, Thomson JM, Anderson VE, Buynak JD, Ng LM, Bonomo RA.

J Biol Chem. 2005 Oct 21;280(42):35528-36. Epub 2005 Jun 29.


Synthesis and evaluation of 3-(carboxymethylidene)- and 3-(carboxymethyl)penicillinates as inhibitors of beta-lactamase.

Buynak JD, Ghadachanda VR, Vogeti L, Zhang H, Chen H.

J Org Chem. 2005 May 27;70(11):4510-3.


Structure-activity relationships of different beta-lactam antibiotics against a soluble form of Enterococcus faecium PBP5, a type II bacterial transpeptidase.

Hujer AM, Kania M, Gerken T, Anderson VE, Buynak JD, Ge X, Caspers P, Page MG, Rice LB, Bonomo RA.

Antimicrob Agents Chemother. 2005 Feb;49(2):612-8.


Penicillin-derived inhibitors that simultaneously target both metallo- and serine-beta-lactamases.

Buynak JD, Chen H, Vogeti L, Gadhachanda VR, Buchanan CA, Palzkill T, Shaw RW, Spencer J, Walsh TR.

Bioorg Med Chem Lett. 2004 Mar 8;14(5):1299-304.


Evaluation of penicillin-based inhibitors of the class A and B beta-lactamases from Bacillus anthracis.

Beharry Z, Chen H, Gadhachanda VR, Buynak JD, Palzkill T.

Biochem Biophys Res Commun. 2004 Jan 16;313(3):541-5.


Cephalosporin-derived inhibitors of beta-lactamase. Part 4: The C3 substituent.

Buynak JD, Vogeti L, Doppalapudi VR, Solomon GM, Chen H.

Bioorg Med Chem Lett. 2002 Jun 17;12(12):1663-6.


Coupling reactions of cephalosporin sulfones: a stable 3-stannylated cephem.

Buynak JD, Vogeti L, Chen H.

Org Lett. 2001 Sep 20;3(19):2953-6.


Inhibition of class C beta-lactamases: structure of a reaction intermediate with a cephem sulfone.

Crichlow GV, Nukaga M, Doppalapudi VR, Buynak JD, Knox JR.

Biochemistry. 2001 May 29;40(21):6233-9.


The synthesis and evaluation of 3-substituted-7-(alkylidene)cephalosporin sulfones as beta-lactamase inhibitors.

Buynak JD, Doppalapudi VR, Adam G.

Bioorg Med Chem Lett. 2000 May 1;10(9):853-7.


The synthesis and evaluation of 2-substituted-7-(alkylidene)cephalosporin sulfones as beta-lactamase inhibitors.

Buynak JD, Doppalapudi VR, Rao AS, Nidamarthy SD, Adam G.

Bioorg Med Chem Lett. 2000 May 1;10(9):847-51.


The synthesis and evaluation of 6-alkylidene-2'beta-substituted penam sulfones as beta-lactamase inhibitors.

Buynak JD, Rao AS, Doppalapudi VR, Adam G, Petersen PJ, Nidamarthy SD.

Bioorg Med Chem Lett. 1999 Jul 19;9(14):1997-2002.


7-alkylidenecephalosporin esters as inhibitors of human leukocyte elastase.

Buynak JD, Rao AS, Ford GP, Carver C, Adam G, Geng B, Bachmann B, Shobassy S, Lackey S.

J Med Chem. 1997 Oct 10;40(21):3423-33.


Synthesis and biological activity of 7-alkylidenecephems.

Buynak JD, Wu K, Bachmann B, Khasnis D, Hua L, Nguyen HK, Carver CL.

J Med Chem. 1995 Mar 17;38(6):1022-34.


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