Synthesis and evaluation of novologues as C-terminal Hsp90 inhibitors with cytoprotective activity against sensory neuron glucotoxicity

Journal of Medicinal Chemistry

Volumn 55, Issue 12, 2012, Pages 5797-5812

  Kusuma, Bhaskar Reddy ^a   Zhang, Liang ^a   Sundstrom, Teather ^a   Peterson, Laura B ^a   Dobrowsky, Rick T ^a   Blagg, Brian S J ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN DERIVATIVE; HEAT SHOCK PROTEIN 90 INHIBITOR; KU 32; NOVOBIOCIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CELL PROTECTION; CONTROLLED STUDY; DIABETIC NEUROPATHY; DRUG SCREENING; DRUG SYNTHESIS; HYDROGEN BOND; HYDROPHOBICITY; NEUROPROTECTION; NEWBORN; NONHUMAN; RAT; SENSORY NERVE CELL;

CHEMISTRY TECHNIQUES, SYNTHETIC; CYTOPROTECTION; GLUCOSE; HSP90 HEAT-SHOCK PROTEINS; HUMANS; MODELS, MOLECULAR; NEUROPROTECTIVE AGENTS; PROTEIN CONFORMATION; SENSORY RECEPTOR CELLS;

EID: 84863110390     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300544c     Document Type: Article

References (30)

1. Veves, A.; Backonja, M.; Malik, R. A. Painful diabetic neuropathy: epidemiology, natural history, early diagnosis, and treatment options Pain Med. 2008, 9, 660-674
2. Tomlinson, D. R.; Gardiner, N. J. Glucose neurotoxicity Nature Rev. Neurosci. 2008, 9 (1) 36-45
3. Mayer, M. P.; Bukau, B. Hsp70 chaperones: cellular functions and molecular mechanism Cell. Mol. Life Sci. 2005, 62 (6) 670-84
4. Peterson, L. B.; Blagg, B. S. To fold or not to fold: modulation and consequences of Hsp90 inhibition Future Med. Chem. 2009, 1 (2) 267-283
5. Burlison, J. A.; Neckers, L.; Smith, A. B.; Maxwell, A.; Blagg, B. S. J. Novobiocin: Redesigning a DNA Gyrase Inhibitor for Selective Inhibition of Hsp90 J. Am. Chem. Soc. 2006, 128, 15529-15536
6. Zhang, L.; Yu, C.; Vasquez, F. E.; Galeva, N.; Onyango, I.; Swerdlow, R. H.; Dobrowsky, R. T. Hyperglycemia alters the schwann cell mitochondrial proteome and decreases coupled respiration in the absence of superoxide production J. Proteome Res. 2010, 9 (1) 458-471
7. Zhang, L.; Zhao, H.; Blagg, B. S.; Dobrowsky, R. T.; C-Terminal, A Heat Shock Protein 90 Inhibitor Decreases Hyperglycemia-induced Oxidative Stress and Improves Mitochondrial Bioenergetics in Sensory Neurons J. Proteome Res. 2012, 11, 129-137
8. Obrosova, I. G. Diabetes and the peripheral nerve Biochim. Biophys. Acta 2009, 10, 931-940
9. Akude, E.; Zherebitskaya, E.; Roy Chowdhury, S. K.; Girling, K.; Fernyhough, P. 4-Hydroxy-2-Nonenal Induces Mitochondrial Dysfunction and Aberrant Axonal Outgrowth in Adult Sensory Neurons that Mimics Features of Diabetic Neuropathy Neurotox. Res. 2009, 1, 28-38
10. Muchowski, P. J.; Wacker, J. L. Modulation of neurodegeneration by molecular chaperones Nature Rev. Neurosci. 2005, 6 (1) 11-22
11. Baseler, W. A.; Dabkowski, E. R.; Williamson, C. L.; Croston, T. L.; Thapa, D.; Powell, M. J.; Razunguzwa, T. T.; Hollander, J. M. Proteomic alterations of distinct mitochondrial subpopulations in the type 1 diabetic heart: contribution of protein import dysfunction Am. J. Physiol.: Regul. Integr. Comp. Physiol. 2011, 300 (2) R186-200
12. Urban, M. J.; Li, C.; Yu, C.; Lu, Y.; Krise, J. M.; McIntosh, M. P.; Rajewski, R. A.; Blagg, B. S. J.; Dobrowsky, R. T. Inhibiting Heat Shock Protein 90 Reverses Sensory Hypoalgesia in Diabetic Mice ASN Neuro 2010, 2, 189-199
13. Burlison, J. A.; Avila, C.; Vielhauer, G.; Lubbers, D. J.; Holzbeierlein, J.; Blagg, B. S. Development of novobiocin analogues that manifest anti-proliferative activity against several cancer cell lines J. Org. Chem. 2008, 73 (6) 2130-2137
14. Donnelly, A. C.; Mays, J. R.; Burlison, J. A.; Nelson, J. T.; Vielhauer, G.; Holzbeierlein, J.; Blagg, B. S. J. The Design, Synthesis, and Evaluation of Coumarin Ring Derivatives of the Novobiocin Scaffold that Exhibit Antiproliferative Activity J. Org. Chem. 2008, 73 (22) 8901-8920
15. Matts, R. L.; Dixit, A.; Peterson, L. B.; Sun, L.; Voruganti, S.; Kalyanaraman, P.; Hartson, S. D.; Verkhivker, G. M.; Blagg, B. S. J. Elucidation of the Hsp90 C-Terminal Inhibitor Binding Site ACS Chem. Biol. 2011, 6, 800-807
16. Lee, M.; Gubernator, N. G.; Sulzer, D.; Sames, D. Development of pH-Responsive Fluorescent False Neurotransmitters J. Am. Chem. Soc. 2010, 132 (26) 8828-8830
17. Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Suzuki-Miyaura Cross-Coupling Reactions Mediated by Palladium/Imidazolium Salt Systems Organometallics 2002, 21 (14) 2866-2873
18. Olson, J. P.; Gichinga, M. G.; Butala, E.; Navarro, H. A.; Gilmour, B. P.; Carroll, F. I. Synthesis and evaluation of 1,2,4-methyltriazines as mGluR5 antagonists Org. Biomol. Chem. 2011, 9 (11) 4276-4286
19. Fuganti, C.; Sacchetti, A. Biocatalytic enantioselective approach to 3-aryl-2-nitropropanols: synthesis of enantioenriched (R)-5-methoxy-3- aminochroman, a key precursor to the antidepressant drug Robalzotan J. Mol. Catal. B: Enzym. 2010, 66 (3-4) 276-284
20. Wood, K.; Black, D. S.; Kumar, N. Ring closing metathesis strategies towards functionalised 1,7-annulated 4,6-dimethoxyindoles Tetrahedron 2011, 67 (22) 4093-4102
21. Kusuma, B. R.; Peterson, L. B.; Zhao, H.; Vielhauer, G.; Holzbeierlein, J.; Blagg, B. S. J. Targeting the Heat Shock Protein 90 Dimer with Dimeric Inhibitors J. Med. Chem. 2011, 54 (18) 6234-6253
22. Oozeki, H.; Tajima, R.; Nihei, K-I. Molecular design of potent tyrosinase inhibitors having the bibenzyl skeleton Bioorg. Med. Chem. Lett. 2008, 18, 5252-5254
23. Bryce, M. R.; Gardiner, J. M. Functionalised (±)-cephalotaxine analogues J. Chem. Soc., Chem. Commun. 1989, 16, 1162-1164
24. Pei, Z.; Li, X.; von Geldern, T. W.; Madar, D. J.; Longenecker, K.; Yong, H.; Lubben, T. H.; Stewart, K. D.; Zinker, B. A.; Backes, B. J.; Judd, A. S.; Mulhern, M.; Ballaron, S. J.; Stashko, M. A.; Mika, A. K.; Beno, D. W. A.; Reinhart, G. A.; Fryer, R. M.; Preusser, L. C.; Kempf-Grote, A. J.; Sham, H. L.; Trevillyan, J. M. Discovery of ((4 R,5 S)-5-Amino-4-(2,4,5-trifluorophenyl) cyclohex-1-enyl)-(3- (trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3- a ]pyrazin-7(8 H)-yl)methanone (ABT-341), a Highly Potent, Selective, Orally Efficacious, and Safe Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes J. Med. Chem. 2006, 49 (22) 6439-6442
25. Andrieux, C. P.; Farriol, M.; Gallardo, I.; Marquet, J. Thermodynamics and kinetics of homolytic cleavage of carbon-oxygen bonds in radical anions obtained by electrochemical reduction of alkyl aryl ethers J. Chem. Soc., Perkin Trans. 2 2002, 5) 985-990
26. Calamini, B.; Silva, M. C.; Madoux, F.; Hutt, D. M.; Khanna, S.; Chalfant, M. A.; Saldanha, S. A.; Hodder, P.; Tait, B. D.; Garza, D.; Balch, W. E.; Morimoto, R. I. Small-molecule proteostasis regulators for protein conformational diseases Nature Chem. Biol. 2012, 8 (2) 185-196
27. Chen, W.; Mi, R.; Haughey, N.; Oz, M.; Höke, A. Immortalization and characterization of a nociceptive dorsal root ganglion sensory neuronal line J. Peripher. Nerv. Syst. 2007, 12 (2) 121-130
28. Zhang, L.; Zhao, H.; Blagg, B. S. J.; Dobrowsky, R. T. C-Terminal Heat Shock Protein 90 Inhibitor Decreases Hyperglycemia-Induced Oxidative Stress and Improves Mitochondrial Bioenergetics in Sensory Neurons J. Proteome Res. 2012, 11, 2581-2593
29. Vincent, A. M.; Kato, K.; McLean, L. L.; Soules, M. E.; Feldman, E. L. Sensory Neurons and Schwann Cells Respond to Oxidative Stress by Increasing Antioxidant Defense Mechanisms Antioxid. Redox Signaling 2009, 11, 425-438
30. Vincent, A. M.; Stevens, M. J.; Backus, C.; McLean, L. L.; Feldman, E. L. Cell culture modeling to test therapies against hyperglycemia-mediated oxidative stress and injury Antioxid. Redox Signaling 2005, 7 (11-12) 1494-1506