Michael Craig Pirrung

Title(s)Professor, Pharmaceutical Sciences
Address101 Theory, Suite 100
Irvine CA 92697-3958
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    Collapse Research 
    Collapse Research Activities and Funding
    Sustainable Synthesis of Enfuvirtide
    NIH R21AI106597Jul 26, 2013 - Jun 30, 2016
    Role: Principal Investigator
    Medicinal Chemistry and Biology of Oral Insulin Mimics
    NIH R01DK060532Jul 15, 2003 - May 31, 2007
    Role: Principal Investigator
    COMBINATORIAL APPROACHES TO ANTI-SMALLPOX AGENTS
    NIH U01AI048521Aug 15, 2000 - Jun 30, 2005
    Role: Principal Investigator
    BIOORGANIC CHEMISTRY OF ANTIBACTERIALS
    NIH R01AI042151Sep 30, 1998 - Aug 31, 2002
    Role: Principal Investigator
    CHEMISTRY-BIOLOGY INTERFACE TRAINING PROGRAM
    NIH T32GM008558Sep 1, 1994 - Jun 30, 2004
    Role: Principal Investigator
    BIOORGANIC PHOTOCHEMISTRY
    NIH R01GM046720Aug 1, 1992 - Jul 1, 2002
    Role: Principal Investigator
    MOLECULAR METAPHORS IN BIOORGANIC CHEMISTRY
    NIH R01GM043816Apr 1, 1991 - Jun 30, 1994
    Role: Principal Investigator
    METHODS FOR HETEROCYCLE SYNTHESIS
    NIH R01GM038226Apr 1, 1987 - Mar 31, 1990
    Role: Principal Investigator
    SYNTHESIS OF ANTITUMOR PENTALENOLACTONES
    NIH R01AI020485Jul 1, 1983 - Dec 31, 1986
    Role: Principal Investigator

    Collapse Bibliographic 
    Collapse Publications
    Publications listed below are automatically derived from MEDLINE/PubMed and other sources, which might result in incorrect or missing publications. Researchers can login to make corrections and additions, or contact us for help. to make corrections and additions.
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    1. Cannabichromene Racemization and Absolute Stereochemistry Based on a Cannabicyclol Analog. J Org Chem. 2021 06 18; 86(12):8036-8040. Agua AR, Barr PJ, Marlowe CK, Pirrung MC. PMID: 34078070.
      View in: PubMed   Mentions:    Fields:    Translation:Animals
    2. Spider web biomonitoring: A cost-effective source apportionment approach for urban particulate matter. Environ Pollut. 2021 May 08; 286:117328. van Laaten N, von Tümpling W, Merten D, Bro R, Schäfer T, Pirrung M. PMID: 33990052.
      View in: PubMed   Mentions:    Fields:    
    3. Synthetic Access to Cannabidiol and Analogs as Active Pharmaceutical Ingredients. J Med Chem. 2020 11 12; 63(21):12131-12136. Pirrung MC. PMID: 32531156.
      View in: PubMed   Mentions:    Fields:    Translation:Animals
    4. Syrbactin proteasome inhibitor TIR-199 overcomes bortezomib chemoresistance and inhibits multiple myeloma tumor growth in vivo. Leuk Res. 2020 01; 88:106271. Pierce MR, Robinson RM, Ibarra-Rivera TR, Pirrung MC, Dolloff NG, Bachmann AS. PMID: 31778912.
      View in: PubMed   Mentions: 2     Fields:    Translation:HumansAnimalsCells
    5. Synthesis and bioluminescence of thioluciferin. Bioorg Med Chem Lett. 2019 10 01; 29(19):126591. Pirrung MC, Carlson AD, De Howitt N, Liao J. PMID: 31471166.
      View in: PubMed   Mentions:    Fields:    Translation:Animals
    6. Thiasyrbactins Induce Cell Death via Proteasome Inhibition in Multiple Myeloma Cells. Anticancer Res. 2018 Oct; 38(10):5607-5613. Pierce MR, Bakas NA, Pirrung MC, Bachmann AS. PMID: 30275178.
      View in: PubMed   Mentions: 1     Fields:    Translation:HumansCells
    7. Immunoproteasome inhibition and bioactivity of thiasyrbactins. Bioorg Med Chem. 2018 01 15; 26(2):401-412. Bakas NA, Schultz CR, Yco LP, Roberts CC, Chang CA, Bachmann AS, Pirrung MC. PMID: 29269255.
      View in: PubMed   Mentions: 2     Fields:    Translation:HumansCells
    8. ß-Deuterium Isotope Effects on Firefly Luciferase Bioluminescence. ChemistryOpen. 2017 12; 6(6):697-700. Pirrung MC, Dorsey A, Howitt N, Liao J. PMID: 29226056.
      View in: PubMed   Mentions:
    9. Native Serine Peptide Assembly: Scope and Utility. European J Org Chem. 2016 Dec; 2016(34):5633-5636. Pirrung MC, Schreihans RS. PMID: 28111523.
      View in: PubMed   Mentions:
    10. Correction: Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation. Org Biomol Chem. 2016 09 26; 14(38):9159. Pirrung MC, Zhang F, Ambadi S, Gangadhara Rao Y. PMID: 27714303.
      View in: PubMed   Mentions:    Fields:    
    11. Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation. Org Biomol Chem. 2016 Sep 21; 14(35):8367-75. Pirrung MC, Zhang F, Ambadi S, Gangadhara Rao Y. PMID: 27533920.
      View in: PubMed   Mentions: 1     Fields:    Translation:Cells
    12. Syrbactin Structural Analog TIR-199 Blocks Proteasome Activity and Induces Tumor Cell Death. J Biol Chem. 2016 Apr 15; 291(16):8350-62. Bachmann AS, Opoku-Ansah J, Ibarra-Rivera TR, Yco LP, Ambadi S, Roberts CC, Chang CE, Pirrung MC. PMID: 26907687.
      View in: PubMed   Mentions: 4     Fields:    Translation:HumansAnimalsCells
    13. Synthesis and bioluminescence of difluoroluciferin. Bioorg Med Chem Lett. 2014 Oct 15; 24(20):4881-3. Pirrung MC, Biswas G, De Howitt N, Liao J. PMID: 25239851.
      View in: PubMed   Mentions: 4     Fields:    Translation:Cells
    14. The genesis of microarrays. Biochem Mol Biol Educ. 2014 Mar-Apr; 42(2):106-13. Pirrung MC, Southern EM. PMID: 24344052.
      View in: PubMed   Mentions: 1     Fields:    Translation:Humans
    15. Catalyzed Claisen rearrangements of O-allyl kojates. Tetrahedron Lett. 2013 Jul 17; 54(29). Pirrung MC, Nalbandian JN. PMID: 24187389.
      View in: PubMed   Mentions:    Fields:    
    16. Repositioning of Verrucosidin, a purported inhibitor of chaperone protein GRP78, as an inhibitor of mitochondrial electron transport chain complex I. PLoS One. 2013; 8(6):e65695. Thomas S, Sharma N, Gonzalez R, Pao PW, Hofman FM, Chen TC, Louie SG, Pirrung MC, Schönthal AH. PMID: 23755268.
      View in: PubMed   Mentions: 7     Fields:    Translation:HumansCells
    17. A fluorescent amino acid probe to monitor efficiency of peptide conjugation to glass surfaces for high density microarrays. Mol Biosyst. 2012 Mar; 8(3):879-87. Zhao Y, Pirrung MC, Liao J. PMID: 22241083.
      View in: PubMed   Mentions:    Fields:    Translation:Cells
    18. Syringolin B-inspired proteasome inhibitor analogue TIR-203 exhibits enhanced biological activity in multiple myeloma and neuroblastoma. Pharm Biol. 2012 Jan; 50(1):25-9. Opoku-Ansah J, Ibarra-Rivera TR, Pirrung MC, Bachmann AS. PMID: 22196580.
      View in: PubMed   Mentions: 5     Fields:    Translation:HumansCells
    19. Novel proteasome-inhibitory syrbactin analogs inducing endoplasmic reticulum stress and apoptosis in hematological tumor cell lines. Biochem Pharmacol. 2011 Sep 15; 82(6):600-9. Anshu A, Thomas S, Agarwal P, Ibarra-Rivera TR, Pirrung MC, Schönthal AH. PMID: 21736873.
      View in: PubMed   Mentions: 6     Fields:    Translation:HumansCells
    20. Sensitized two-photon photochemical deprotection. Chem Commun (Camb). 2010 Aug 07; 46(29):5313-5. Pirrung MC, Dore TM, Zhu Y, Rana VS. PMID: 20552130.
      View in: PubMed   Mentions: 5     Fields:    Translation:Cells
    21. Total synthesis of syringolin A and B. Org Lett. 2010 May 21; 12(10):2402-5. Pirrung MC, Biswas G, Ibarra-Rivera TR. PMID: 20426399.
      View in: PubMed   Mentions: 11     Fields:    Translation:Cells
    22. His-tags lighten up and lose their inhibitions. Proc Natl Acad Sci U S A. 2010 Apr 06; 107(14):6123-4. Pirrung MC. PMID: 20363960.
      View in: PubMed   Mentions: 1     Fields:    Translation:Cells
    23. Iodine scanning of a phenazine inhibitor of vacuolar sorting. Bioorg Med Chem Lett. 2010 Mar 01; 20(5):1496-9. Surpin M, Zou Y, Xiong C, Raikhel NV, Pirrung MC. PMID: 20153185.
      View in: PubMed   Mentions:    Fields:    Translation:AnimalsCells
    24. Multicomponent reactions of convertible isonitriles. J Org Chem. 2009 Jun 05; 74(11):4110-7. Pirrung MC, Ghorai S, Ibarra-Rivera TR. PMID: 19408909.
      View in: PubMed   Mentions: 9     Fields:    
    25. Multicomponent reactions of cyclobutanones. J Org Chem. 2009 Apr 17; 74(8):2958-63. Pirrung MC, Wang J. PMID: 19354324.
      View in: PubMed   Mentions: 2     Fields:    
    26. Small molecule activators of the Trk receptors for neuroprotection. BMC Neurosci. 2008 Dec 03; 9 Suppl 2:S1. Webster NJ, Pirrung MC. PMID: 19090982.
      View in: PubMed   Mentions: 18     Fields:    Translation:HumansAnimalsCells
    27. Hydrophobicity and mixing effects on select heterogeneous, water-accelerated synthetic reactions. J Org Chem. 2008 Nov 21; 73(22):8723-30. Pirrung MC, Das Sarma K, Wang J. PMID: 18954111.
      View in: PubMed   Mentions: 4     Fields:    
    28. Ethylene receptor antagonists: strained alkenes are necessary but not sufficient. Chem Biol. 2008 Apr; 15(4):313-21. Pirrung MC, Bleecker AB, Inoue Y, Rodríguez FI, Sugawara N, Wada T, Zou Y, Binder BM. PMID: 18420138.
      View in: PubMed   Mentions: 4     Fields:    Translation:AnimalsCells
    29. Preparation of methyl ester precursors of biologically active agents. Biotechniques. 2008 Mar; 44(3):377-84. Zou Y, Rojas-Pierce M, Raikhel N, Pirrung M. PMID: 18361791.
      View in: PubMed   Mentions:    Fields:    Translation:Cells
    30. Modular synthesis of candidate indole-based insulin mimics by Claisen rearrangement. Org Lett. 2008 Mar 20; 10(6):1151-4. Xiong X, Pirrung MC. PMID: 18303898.
      View in: PubMed   Mentions: 7     Fields:    Translation:Cells
    31. Quinone replacements for small molecule insulin mimics. Chembiochem. 2008 Feb 15; 9(3):360-2. Pirrung MC, Deng L, Lin B, Webster NJ. PMID: 18232038.
      View in: PubMed   Mentions:    Fields:    Translation:HumansAnimalsCells
    32. Identification of novel orally available small molecule insulin mimetics. J Pharmacol Exp Ther. 2007 Nov; 323(2):579-85. Lin B, Li Z, Park K, Deng L, Pai A, Zhong L, Pirrung MC, Webster NJ. PMID: 17687071.
      View in: PubMed   Mentions: 7     Fields:    Translation:AnimalsCells
    33. Glyceraldehyde 3-phosphate dehydrogenase is a cellular target of the insulin mimic demethylasterriquinone B1. J Med Chem. 2007 Jul 26; 50(15):3423-6. Kim H, Deng L, Xiong X, Hunter WD, Long MC, Pirrung MC. PMID: 17595071.
      View in: PubMed   Mentions: 3     Fields:    Translation:HumansCells
    34. Parallel synthesis of indolylquinones and their cell-based insulin mimicry. J Comb Chem. 2007 Sep-Oct; 9(5):844-54. Pirrung MC, Li Z, Hensley E, Liu Y, Tanksale A, Lin B, Pai A, Webster NJ. PMID: 17595147.
      View in: PubMed   Mentions: 2     Fields:    Translation:Cells
    35. Practical synthesis of 7-prenylindole. J Org Chem. 2007 Jul 20; 72(15):5832-4. Xiong X, Pirrung MC. PMID: 17580906.
      View in: PubMed   Mentions: 1     Fields:    
    36. Neuroprotection by small molecule activators of the nerve growth factor receptor. J Pharmacol Exp Ther. 2007 Jul; 322(1):59-69. Lin B, Pirrung MC, Deng L, Li Z, Liu Y, Webster NJ. PMID: 17468299.
      View in: PubMed   Mentions: 10     Fields:    Translation:AnimalsCells
    37. Versatile, fragrant, convertible isonitriles. J Am Chem Soc. 2006 Sep 13; 128(36):11772-3. Pirrung MC, Ghorai S. PMID: 16953613.
      View in: PubMed   Mentions: 6     Fields:    
    38. Mechanistic studies on the photochemical deprotection of 3',5'-dimethoxybenzoin esters. Photochem Photobiol. 2006 Sep-Oct; 82(5):1258-64. Pirrung MC, Ye T, Zhou Z, Simon JD. PMID: 16752957.
      View in: PubMed   Mentions: 2     Fields:    
    39. Molecular validation of LpxC as an antibacterial drug target in Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2006 Jun; 50(6):2178-84. Mdluli KE, Witte PR, Kline T, Barb AW, Erwin AL, Mansfield BE, McClerren AL, Pirrung MC, Tumey LN, Warrener P, Raetz CR, Stover CK. PMID: 16723580.
      View in: PubMed   Mentions: 28     Fields:    Translation:Cells
    40. Acceleration of organic reactions through aqueous solvent effects. Chemistry. 2006 Feb 01; 12(5):1312-7. Pirrung MC. PMID: 16189838.
      View in: PubMed   Mentions: 9     Fields:    
    41. Adding precision tools to the plant biologists' toolbox with chemical genomics. Plant Physiol. 2005 Jun; 138(2):563-4. Raikhel N, Pirrung M. PMID: 15955916.
      View in: PubMed   Mentions: 10     Fields:    Translation:Cells
    42. Combinatorial optimization of isatin-beta-thiosemicarbazones as anti-poxvirus agents. J Med Chem. 2005 Apr 21; 48(8):3045-50. Pirrung MC, Pansare SV, Sarma KD, Keith KA, Kern ER. PMID: 15828843.
      View in: PubMed   Mentions: 8     Fields:    Translation:HumansCells
    43. Methyl scanning: total synthesis of demethylasterriquinone B1 and derivatives for identification of sites of interaction with and isolation of its receptor(s). J Am Chem Soc. 2005 Apr 06; 127(13):4609-24. Pirrung MC, Liu Y, Deng L, Halstead DK, Li Z, May JF, Wedel M, Austin DA, Webster NJ. PMID: 15796526.
      View in: PubMed   Mentions: 9     Fields:    Translation:AnimalsCells
    44. Organometallic routes to 2,5-dihydroxy-3-(indol-3-yl)benzoquinones. Synthesis of demethylasterriquinone B4. J Org Chem. 2005 Apr 01; 70(7):2537-42. Pirrung MC, Fujita K, Park K. PMID: 15787540.
      View in: PubMed   Mentions: 3     Fields:    
    45. Benzo[c]phenanthrene adducts and nogalamycin inhibit DNA transesterification by vaccinia topoisomerase. J Biol Chem. 2004 May 28; 279(22):23335-42. Yakovleva L, Handy CJ, Sayer JM, Pirrung M, Jerina DM, Shuman S. PMID: 15044474.
      View in: PubMed   Mentions: 4     Fields:    Translation:Cells
    46. Multicomponent reactions are accelerated in water. J Am Chem Soc. 2004 Jan 21; 126(2):444-5. Pirrung MC, Sarma KD. PMID: 14719923.
      View in: PubMed   Mentions: 23     Fields:    
    47. Combinatorial discovery of two-photon photoremovable protecting groups. Proc Natl Acad Sci U S A. 2003 Oct 28; 100(22):12548-53. Pirrung MC, Pieper WH, Kaliappan KP, Dhananjeyan MR. PMID: 14557545.
      View in: PubMed   Mentions: 1     Fields:    
    48. Inhibition of Cdc25 phosphatases by indolyldihydroxyquinones. J Med Chem. 2003 Jun 19; 46(13):2580-8. Sohn J, Kiburz B, Li Z, Deng L, Safi A, Pirrung MC, Rudolph J. PMID: 12801222.
      View in: PubMed   Mentions: 6     Fields:    Translation:HumansCells
    49. Modular, parallel synthesis of an illudinoid combinatorial library. Org Lett. 2003 May 29; 5(11):1983-5. Pirrung MC, Liu H. PMID: 12762702.
      View in: PubMed   Mentions: 1     Fields:    Translation:AnimalsCells
    50. Signaling effects of demethylasterriquinone B1, a selective insulin receptor modulator. Chembiochem. 2003 May 09; 4(5):379-85. Webster NJ, Park K, Pirrung MC. PMID: 12740809.
      View in: PubMed   Mentions: 7     Fields:    Translation:HumansAnimalsCells
    51. High-throughput catch-and-release synthesis of oxazoline hydroxamates. Structure-activity relationships in novel inhibitors of Escherichia coli LpxC: in vitro enzyme inhibition and antibacterial properties. J Am Chem Soc. 2003 Feb 12; 125(6):1575-86. Pirrung MC, Tumey LN, McClerren AL, Raetz CR. PMID: 12568618.
      View in: PubMed   Mentions: 12     Fields:    Translation:Cells
    52. Synthesis of 2,5-dihydroxy-3-(indol-3-yl)benzoquinones by acid-catalyzed condensation of indoles with 2,5-dichlorobenzoquinone. J Org Chem. 2002 Nov 29; 67(24):8374-88. Pirrung MC, Deng L, Li Z, Park K. PMID: 12444614.
      View in: PubMed   Mentions: 3     Fields:    
    53. Total syntheses of demethylasterriquinone B1, an orally active insulin mimetic, and demethylasterriquinone A1. J Org Chem. 2002 Nov 15; 67(23):7919-26. Pirrung MC, Li Z, Park K, Zhu J. PMID: 12423119.
      View in: PubMed   Mentions: 1     Fields:    Translation:AnimalsCells
    54. Inhibition of the antibacterial target UDP-(3-O-acyl)-N-acetylglucosamine deacetylase (LpxC): isoxazoline zinc amidase inhibitors bearing diverse metal binding groups. J Med Chem. 2002 Sep 12; 45(19):4359-70. Pirrung MC, Tumey LN, Raetz CR, Jackman JE, Snehalatha K, McClerren AL, Fierke CA, Gantt SL, Rusche KM. PMID: 12213077.
      View in: PubMed   Mentions: 13     Fields:    Translation:Cells
    55. (19)F-encoded combinatorial libraries: discovery of selective metal binding and catalytic peptoids. J Comb Chem. 2002 Jul-Aug; 4(4):329-44. Pirrung MC, Park K, Tumey LN. PMID: 12099851.
      View in: PubMed   Mentions: 8     Fields:    Translation:Cells
    56. Arrayed primer extension computing with variant mRNA splice forms. Multiple isoforms of CD44 in a human breast tumor. J Am Chem Soc. 2002 May 08; 124(18):4934-5. Kim H, Pirrung MC. PMID: 11982338.
      View in: PubMed   Mentions: 1     Fields:    Translation:HumansCells
    57. How to make a DNA chip. Angew Chem Int Ed Engl. 2002 Apr 15; 41(8):1276-89. Pirrung MC. PMID: 19750752.
      View in: PubMed   Mentions: 38     Fields:    
    58. Rhodium chemzymes: Michaelis-Menten kinetics in dirhodium(II) carboxylate-catalyzed carbenoid reactions. J Am Chem Soc. 2002 Feb 13; 124(6):1014-23. Pirrung MC, Liu H, Morehead AT. PMID: 11829610.
      View in: PubMed   Mentions: 5     Fields:    Translation:Cells
    59. Pentadienylnitrobenzyl and Pentadienylnitropiperonyl Photochemically Removable Protecting Groups. J Org Chem. 1999 Jul 09; 64(14):5042-5047. Pirrung MC, Lee YR, Park K, Springer JB. PMID: 34237832.
      View in: PubMed   Mentions:    Fields:    
    60. Rhodium-Mediated Dipolar Cycloaddition of Diazoquinolinediones. J Org Chem. 1999 May 14; 64(10):3642-3649. Pirrung MC, Blume F. PMID: 11674492.
      View in: PubMed   Mentions: 5     Fields:    
    61. Spatially Addressable Combinatorial Libraries. Chem Rev. 1997 Apr 01; 97(2):473-488. Pirrung MC. PMID: 11848879.
      View in: PubMed   Mentions: 11     Fields:    
    62. O-Alkyl Hydroxamates as Metaphors of Enzyme-Bound Enolate Intermediates in Hydroxy Acid Dehydrogenases. Inhibitors of Isopropylmalate Dehydrogenase, Isocitrate Dehydrogenase, and Tartrate Dehydrogenase(1). J Org Chem. 1996 Jul 12; 61(14):4527-4531. Pirrung MC, Han H, Chen J. PMID: 11667376.
      View in: PubMed   Mentions: 2     Fields:    
    63. Cofactor-Directed, Time-Dependent Inhibition of Thiamine Enzymes by the Fungal Toxin Moniliformin. J Org Chem. 1996 Apr 19; 61(8):2592-2593. Pirrung MC, Nauhaus SK, Singh B. PMID: 11667082.
      View in: PubMed   Mentions: 2     Fields:    
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