A high throughput screen identifies potent and selective inhibitors to human epithelial 15-lipoxygenase-2

PLoS ONE

Volumn 9, Issue 8, 2014, Pages

  Jameson II, J Brian ^a   Kantz, Auric ^a   Schultz, Lena ^b   Kalyanaraman, Chakrapani ^c   Jacobson, Matthew P ^c   Maloney, David J ^b   Jadhav, Ajit ^b   Simeonov, Anton ^b   Holman, Theodore R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

15 LIPOXYGENASE 1; 15 LIPOXYGENASE 2; 15 LIPOXYGENASE 2 INHIBITOR; ARACHIDONATE 12 LIPOXYGENASE; ARACHIDONATE 15 LIPOXYGENASE; ARACHIDONATE 5 LIPOXYGENASE; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; FERROUS ION; LIPOXYGENASE INHIBITOR; ML 094; ML 127; ML 351; ML 355; MLS 000536924; MLS 000545091; UNCLASSIFIED DRUG;

ARTICLE; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; ENZYME ACTIVE SITE; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH THROUGHPUT SCREENING; IC 50; MOLECULAR DOCKING; STEADY STATE; CHEMISTRY; ENZYMOLOGY; EPITHELIUM; HUMAN; KINETICS; METABOLISM; PROTEIN CONFORMATION;

ARACHIDONATE 15-LIPOXYGENASE; DRUG EVALUATION, PRECLINICAL; EPITHELIUM; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; KINETICS; LIPOXYGENASE INHIBITORS; MOLECULAR DOCKING SIMULATION; PROTEIN CONFORMATION;

EID: 84905821982     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0104094     Document Type: Article

References (31)

1. Klil-Drori AJ, Ariel A (2013) 15-Lipoxygenases in cancer: A double-edged sword?. Prostaglandins Other Lipid Mediat 106: 16-22.
2. Brash AR, Boeglin WE, Chang MS (1997) Discovery of a second 15S-lipoxygenase in humans. Proc Natl Acad Sci USA 94: 6148-6152. (Pubitemid 27270652)
3. Jack GS, Brash AR, Olson SJ, Manning S, Coffey CS, et al. (2000) Reduced 15-lipoxygenase-2 immunostaining in prostate adenocarcinoma: correlation with grade and expression in high-grade prostatic intraepithelial neoplasia. Hum Pathol 31: 1146-1154.
4. Suraneni MV, Schneider-Broussard R, Moore JR, Davis TC, Maldonado CJ, et al. (2010) Transgenic expression of 15-lipoxygenase 2 (15-LOX2) in mouse prostate leads to hyperplasia and cell senescence. Oncogene 29: 4261-4275.
5. Zuo X, Peng Z, Wu Y, Moussalli MJ, Yang XL, et al. (2012) Effects of guttargeted 15-LOX-1 transgene expression on colonic tumorigenesis in mice. J Natl Cancer Inst 104: 709-716.
6. O'Flaherty JT, Hu Y, Wooten RE, Horita DA, Samuel MP, et al. (2012) 5-lipoxygenase metabolites of docosahexaenoic acid inhibit prostate cancer cell proliferation and survival. PLoS ONE 7: e45480.
7. Bhatia B, Maldonado CJ, Tang S, Chandra D, Klein RD, et al. (2003) Subcellular localization and tumor-suppressive functions of 15-lipoxygenase 2 (15-LOX2) and its splice variants. J Biol Chem 278: 25091-25100. (Pubitemid 37548673)
8. Rai G, Kenyon V, Jadhav A, Schultz L, Armstrong M, et al. (2010) Discovery of potent and selective inhibitors of human reticulocyte 15-lipoxygenase-1. J Med Chem 53: 7392-7404.
9. Whitman S, Gezginci M, Timmermann BN, Holman TR (2002) Structure-activity relationship studies of nordihydroguaiaretic acid inhibitors toward soybean, 12-human, and 15-human lipoxygenase. J Med Chem 45: 2659-2661. (Pubitemid 34595235)
10. Segraves EN, Shah RR, Segraves NL, Johnson TA, Whitman S, et al. (2004) Probing the activity differences of simple and complex brominated aryl compounds against 15-soybean, 15-human, and 12-human lipoxygenase. J Med Chem 47: 4060-4065. (Pubitemid 38970967)
11. Cichewicz RH, Kenyon VA, Whitman S, Morales NM, Arguello JA, et al. (2004) Redox inactivation of human 15-lipoxygenase by marine-derived meroditerpenes and synthetic chromanes: archetypes for a unique class of selective and recyclable inhibitors. Journal of the American Chemical Society 126: 14910-14920. (Pubitemid 39532173)
12. Amagata T, Whitman S, Johnson TA, Stessman CC, Loo CP, et al. (2003) Exploring Sponge-Derived Terpenoids for Their Potency and Selectivity against 12-Human, 15-Human, and 15-Soybean Lipoxygenases. J Nat Prod 66: 230-235. (Pubitemid 36278235)
13. Vasquez-Martinez Y, Ohri RV, Kenyon V, Holman TR, Sepúlveda-Boza S (2007) Structure-activity relationship studies of flavonoids as potent inhibitors of human platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2. Bioorg Med Chem 15: 7408-7425. (Pubitemid 47539136)
14. Deschamps JD, Gautschi JT, Whitman S, Johnson TA, Gassner NC, et al. (2007) Discovery of platelet-type 12-human lipoxygenase selective inhibitors by high-throughput screening of structurally diverse libraries. Bioorg Med Chem 15: 6900-6908. (Pubitemid 47451802)
15. Kenyon V, Rai G, Jadhav A, Schultz L, Armstrong M, et al. (2011) Discovery of potent and selective inhibitors of human platelet-type 12- lipoxygenase. J Med Chem 54: 5485-5497.
16. Luci DK, Jameson JB, Yasgar A, Diaz G, Joshi N, et al. (2014) Synthesis and Structure-Activity Relationship Studies of 4-((2-Hydroxy-3-methoxybenzyl) amino) benzenesulfonamide Derivatives as Potent and Selective Inhibitors of 12-Lipoxygenase. J Med Chem 57: 495-506.
17. Joshi N, Hoobler EK, Perry S, Diaz G, Fox B, et al. (2013) Kinetic and Structural Investigations into the Allosteric and pH Effect on the Substrate Specificity of Human Epithelial 15-Lipoxygenase-2. Biochemistry 52: 8026-8035.
18. Chen XS, Brash AR, Funk CD (1993) Purification and characterization of recombinant histidine-tagged human platelet 12-lipoxygenase expressed in a baculovirus/insect cell system. Eur J Biochem 214: 845-852. (Pubitemid 23188162)
19. Robinson SJ, Hoobler EK, Riener M, Loveridge ST, Tenney K, et al. (2009) Using enzyme assays to evaluate the structure and bioactivity of sponge-derived meroterpenes. J Nat Prod 72: 1857-1863.
20. Rouzer CA, Samuelsson B (1985) On the nature of the 5-lipoxygenase reaction in human leukocytes: enzyme purification and requirement for multiple stimulatory factors. Proc Natl Acad Sci USA 82: 6040-6044. (Pubitemid 16223894)
21. Inglese J, Auld DS, Jadhav A, Johnson RL, Simeonov A, et al. (2006) Quantitative high-throughput screening: a titration-based approach that efficiently identifies biological activities in large chemical libraries. Proc Natl Acad Sci USA 103: 11473-11478. (Pubitemid 44182476)
22. Hoobler EK, Holz C, Holman TR (2013) Pseudoperoxidase investigations of hydroperoxides and inhibitors with human lipoxygenases. Bioorg Med Chem 21: 3894-3899.
23. Kobe MJ, Neau DB, Mitchell CE, Bartlett SG, Newcomer ME (2014) The structure of human 15-lipoxygenase-2 with a substrate mimic. J Biol Chem 289: 8562-8569.
24. Sherman W, Day T, Jacobson MP, Friesner RA, Farid R (2006) Novel procedure for modeling ligand/receptor induced fit effects. J Med Chem 49: 534-553. (Pubitemid 43157487)
25. Rai G, Joshi N, Jung JE, Liu Y, Schultz L, et al. (2014) Potent and Selective Inhibitors of Human Reticulocyte 12/15-Lipoxygenase as Anti-Stroke Therapies. J Med Chem 57: 4035-4048
26. Kalyanaraman C, Bernacki K, Jacobson MP (2005) Virtual screening against highly charged active sites: identifying substrates of alpha-beta barrel enzymes. Biochemistry 44: 2059-2071. (Pubitemid 40223633)
27. Friesner RA, Murphy RB, Repasky MP, Frye LL, Greenwood JR, et al. (2006) Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. J Med Chem 49: 6177-6196. (Pubitemid 44595196)
28. Jiang ZY, Woollard AC, Wolff SP (1991) Lipid hydroperoxide measurement by oxidation of Fe2+ in the presence of xylenol orange. Comparison with the TBA assay and an iodometric method. Lipids 26: 853-856.
29. McMillan RM, Walker ER (1992) Designing therapeutically effective 5-lipoxygenase inhibitors. Trends Pharmacol Sci 13: 323-330.
30. Wecksler AT, Kenyon V, Deschamps JD, Holman TR (2008) Substrate specificity changes for human reticulocyte and epithelial 15-lipoxygenases reveal allosteric product regulation. Biochemistry 47: 7364-7375. (Pubitemid 351991015)
31. Wecksler AT, Kenyon V, Garcia NK, Deschamps JD, van der Donk WA, et al. (2009) Kinetic and structural investigations of the allosteric site in human epithelial 15-lipoxygenase-2. Biochemistry 48: 8721-8730.