메뉴 건너뛰기




Volumn 165, Issue 7, 2012, Pages 2304-2313

Molecular pharmacological profile of a novel thiazolinone-based direct and selective 5-lipoxygenase inhibitor

Author keywords

5 lipoxygenase; asthma; inflammation; leukotrienes; polymorphonuclear leukocytes; virtual screening

Indexed keywords

5 (4 METHOXYBENZYLIDENE) 2 (4 TOLYL) 5H THIAZOL 4 ONE; ARACHIDONATE 12 LIPOXYGENASE; ARACHIDONATE 15 LIPOXYGENASE; ARACHIDONATE 15 LIPOXYGENASE 1; ARACHIDONATE 15 LIPOXYGENASE 2; ARACHIDONATE 5 LIPOXYGENASE; CYCLOOXYGENASE 2; LIPOXYGENASE INHIBITOR; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR; PHOSPHOLIPASE A2; UNCLASSIFIED DRUG;

EID: 84858216778     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2011.01707.x     Document Type: Article
Times cited : (15)

References (48)
  • 1
    • 0037114483 scopus 로고    scopus 로고
    • Hyperforin is a dual inhibitor of cyclooxygenase-1 and 5-lipoxygenase
    • DOI 10.1016/S0006-2952(02)01387-4, PII S0006295202013874
    • Albert D, Zündorf I, Dingermann T, Müller WE, Steinhilber D, Werz O, (2002). Hyperforin is a dual inhibitor of cyclooxygenase-1 and 5-lipoxygenase. Biochem Pharmacol 64: 1767-1775. (Pubitemid 35355728)
    • (2002) Biochemical Pharmacology , vol.64 , Issue.12 , pp. 1767-1775
    • Albert, D.1    Zundorf, I.2    Dingermann, T.3    Muller, W.E.4    Steinhilber, D.5    Werz, O.6
  • 2
    • 81355156238 scopus 로고    scopus 로고
    • Guide to Receptors and Channels (GRAC), 5th Edition
    • Alexander SPH, Mathie A, Peters JA, (2011). Guide to Receptors and Channels (GRAC), 5th Edition. Br J Pharmacol 164 (Suppl. 1): S1-S324.
    • (2011) Br J Pharmacol , vol.164 , Issue.1 SUPPL.
    • Alexander, S.P.H.1    Mathie, A.2    Peters, J.A.3
  • 4
    • 0035808471 scopus 로고    scopus 로고
    • The N-terminal "β-barrel" domain of 5-lipoxygenase is essential for nuclear membrane translocation
    • DOI 10.1074/jbc.M008203200
    • Chen XS, Funk CD, (2001). The N-terminal 'beta-barrel' domain of 5-lipoxygenase is essential for nuclear membrane translocation. J Biol Chem 276: 811-818. (Pubitemid 32050382)
    • (2001) Journal of Biological Chemistry , vol.276 , Issue.1 , pp. 811-818
    • Chen, X.-S.1    Funk, C.D.2
  • 5
    • 67649861052 scopus 로고    scopus 로고
    • Loss of the Alox5 gene impairs leukemia stem cells and prevents chronic myeloid leukemia
    • Chen Y, Hu Y, Zhang H, Peng C, Li S, (2009). Loss of the Alox5 gene impairs leukemia stem cells and prevents chronic myeloid leukemia. Nat Genet 41: 783-792.
    • (2009) Nat Genet , vol.41 , pp. 783-792
    • Chen, Y.1    Hu, Y.2    Zhang, H.3    Peng, C.4    Li, S.5
  • 7
    • 1642297148 scopus 로고    scopus 로고
    • 2+ mobilization and functional leukocyte responses by hyperforin
    • DOI 10.1016/j.bcp.2003.12.020, PII S000629520300964X
    • 2+ mobilization and functional leukocyte responses by hyperforin. Biochem Pharmacol 67: 1531-1539. (Pubitemid 38388215)
    • (2004) Biochemical Pharmacology , vol.67 , Issue.8 , pp. 1531-1539
    • Feisst, C.1    Werz, O.2
  • 8
    • 68549132365 scopus 로고    scopus 로고
    • Hyperforin is a novel type of 5-lipoxygenase inhibitor with high efficacy in vivo
    • Feisst C, Pergola C, Rakonjac M, Rossi A, Koeberle A, Dodt G, et al,. (2009). Hyperforin is a novel type of 5-lipoxygenase inhibitor with high efficacy in vivo. Cell Mol Life Sci 66: 2759-2771.
    • (2009) Cell Mol Life Sci , vol.66 , pp. 2759-2771
    • Feisst, C.1    Pergola, C.2    Rakonjac, M.3    Rossi, A.4    Koeberle, A.5    Dodt, G.6
  • 9
    • 77957240474 scopus 로고    scopus 로고
    • 5-Lipoxygenase inhibitors induce potent anti-proliferative and cytotoxic effects in human tumour cells independently of suppression of 5-lipoxygenase activity
    • Fischer AS, Metzner J, Steinbrink SD, Ulrich S, Angioni C, Geisslinger G, et al,. (2010). 5-Lipoxygenase inhibitors induce potent anti-proliferative and cytotoxic effects in human tumour cells independently of suppression of 5-lipoxygenase activity. Br J Pharmacol 161: 936-949.
    • (2010) Br J Pharmacol , vol.161 , pp. 936-949
    • Fischer, A.S.1    Metzner, J.2    Steinbrink, S.D.3    Ulrich, S.4    Angioni, C.5    Geisslinger, G.6
  • 10
    • 0038661167 scopus 로고    scopus 로고
    • Phosphorylation- and stimulus-dependent inhibition of cellular 5-lipoxygenase activity by nonredox-type inhibitors
    • Fischer L, Szellas D, RAdmark O, Steinhilber D, Werz O, (2003). Phosphorylation- and stimulus-dependent inhibition of cellular 5-lipoxygenase activity by nonredox-type inhibitors. FASEB J 17: 949-951.
    • (2003) FASEB J , vol.17 , pp. 949-951
    • Fischer, L.1    Szellas, D.2    RaDmark, O.3    Steinhilber, D.4    Werz, O.5
  • 11
    • 58649091333 scopus 로고    scopus 로고
    • Phosphorylation of serine 271 on 5-lipoxygenase and its role in nuclear export
    • Flamand N, Luo M, Peters-Golden M, Brock TG, (2009). Phosphorylation of serine 271 on 5-lipoxygenase and its role in nuclear export. J Biol Chem 284: 306-313.
    • (2009) J Biol Chem , vol.284 , pp. 306-313
    • Flamand, N.1    Luo, M.2    Peters-Golden, M.3    Brock, T.G.4
  • 15
    • 0029015335 scopus 로고
    • Mutations at the C-terminal isoleucine and other potential iron ligands of 5-lipoxygenase
    • Hammarberg T, Zhang YY, Lind B, Radmark O, Samuelsson B, (1995). Mutations at the C-terminal isoleucine and other potential iron ligands of 5-lipoxygenase. Eur J Biochem 230: 401-407.
    • (1995) Eur J Biochem , vol.230 , pp. 401-407
    • Hammarberg, T.1    Zhang, Y.Y.2    Lind, B.3    Radmark, O.4    Samuelsson, B.5
  • 16
    • 0034624019 scopus 로고    scopus 로고
    • The N-terminal domain of 5-lipoxygenase binds calcium and mediates calcium stimulation of enzyme activity
    • DOI 10.1074/jbc.M006136200
    • Hammarberg T, Provost P, Persson B, RÃ¥dmark O, (2000). The N-terminal domain of 5-lipoxygenase binds calcium and mediates calcium stimulation of enzyme activity. J Biol Chem 275: 38787-38793. (Pubitemid 32009215)
    • (2000) Journal of Biological Chemistry , vol.275 , Issue.49 , pp. 38787-38793
    • Hammarberg, T.1    Provost, P.2    Persson, B.3    Radmark, O.4
  • 17
    • 76649142718 scopus 로고    scopus 로고
    • 2+-independent arachidonic acid release in human platelets by facilitating cytosolic phospholipase A(2) activation through select phospholipid interactions
    • 2+-independent arachidonic acid release in human platelets by facilitating cytosolic phospholipase A(2) activation through select phospholipid interactions. Biochim Biophys Acta 1801: 462-472.
    • (2010) Biochim Biophys Acta , vol.1801 , pp. 462-472
    • Hoffmann, M.1    Lopez, J.J.2    Pergola, C.3    Feisst, C.4    Pawelczik, S.5    Jakobsson, P.J.6
  • 19
    • 79952800679 scopus 로고    scopus 로고
    • A class of 5-benzylidene-2-phenylthiazolinones with high potency as direct 5-lipoxygenase inhibitors
    • Hofmann B, Barzen S, Rödl CB, Kiehl A, Borig J, Ž ivković A, et al,. (2011). A class of 5-benzylidene-2-phenylthiazolinones with high potency as direct 5-lipoxygenase inhibitors. J Med Chem 54: 1943-1947.
    • (2011) J Med Chem , vol.54 , pp. 1943-1947
    • Hofmann, B.1    Barzen, S.2    Rödl, C.B.3    Kiehl, A.4    Borig, J.5    Živković, A.6
  • 20
    • 22844432867 scopus 로고    scopus 로고
    • 1-Oleoyl-2-acetylglycerol stimulates 5-lipoxygenase activity via a putative (phospho)lipid binding site within the N-terminal C2-like domain
    • DOI 10.1074/jbc.M500068200
    • Hörnig C, Albert D, Fischer L, Hörnig M, RÃ¥dmark O, Steinhilber D, et al,. (2005). 1-Oleoyl-2-acetylglycerol stimulates 5-lipoxygenase activity via a putative (phospho)lipid binding site within the N-terminal C2-like domain. J Biol Chem 280: 26913-26921. (Pubitemid 41040726)
    • (2005) Journal of Biological Chemistry , vol.280 , Issue.29 , pp. 26913-26921
    • Hornig, C.1    Albert, D.2    Fischer, L.3    Hornig, M.4    Radmark, O.5    Steinhilber, D.6    Werz, O.7
  • 21
    • 0037066761 scopus 로고    scopus 로고
    • Molecular basis of the specific subcellular localization of the C2-like domain of 5-lipoxygenase
    • DOI 10.1074/jbc.M112393200
    • Kulkarni S, Das S, Funk CD, Murray D, Cho W, (2002). Molecular basis of the specific subcellular localization of the C2-like domain of 5-lipoxygenase. J Biol Chem 277: 13167-13174. (Pubitemid 34952687)
    • (2002) Journal of Biological Chemistry , vol.277 , Issue.15 , pp. 13167-13174
    • Kulkarni, S.1    Das, S.2    Funk, C.D.3    Murray, D.4    Cho, W.5
  • 22
    • 70450257793 scopus 로고    scopus 로고
    • Accelerated clearance of plasmodium-infected erythrocytes in sickle cell trait and annexin-A7 deficiency
    • Lang PA, Kasinathan RS, Brand VB, Duranton C, Lang C, Koka S, et al,. (2009). Accelerated clearance of plasmodium-infected erythrocytes in sickle cell trait and annexin-A7 deficiency. Cell Physiol Biochem 24: 415-428.
    • (2009) Cell Physiol Biochem , vol.24 , pp. 415-428
    • Lang, P.A.1    Kasinathan, R.S.2    Brand, V.B.3    Duranton, C.4    Lang, C.5    Koka, S.6
  • 24
    • 0026725367 scopus 로고
    • Designing therapeutically effective 5-lipoxygenase inhibitors
    • McMillan RM, Walker ER, (1992). Designing therapeutically effective 5-lipoxygenase inhibitors. Trends Pharmacol Sci 13: 323-330.
    • (1992) Trends Pharmacol Sci , vol.13 , pp. 323-330
    • McMillan, R.M.1    Walker, E.R.2
  • 25
    • 77950259354 scopus 로고    scopus 로고
    • Lipoxygenase inhibitors for cancer prevention: Promises and risks
    • Menna C, Olivieri F, Catalano A, Procopio A, (2010). Lipoxygenase inhibitors for cancer prevention: promises and risks. Curr Pharm Des 16: 725-733.
    • (2010) Curr Pharm des , vol.16 , pp. 725-733
    • Menna, C.1    Olivieri, F.2    Catalano, A.3    Procopio, A.4
  • 26
    • 40849119794 scopus 로고    scopus 로고
    • Development of a method for expression and purification of the regulatory C2-like domain of human 5-lipoxygenase
    • Michel AA, Steinhilber D, Werz O, (2008). Development of a method for expression and purification of the regulatory C2-like domain of human 5-lipoxygenase. Protein Expr Purif 59: 110-116.
    • (2008) Protein Expr Purif , vol.59 , pp. 110-116
    • Michel, A.A.1    Steinhilber, D.2    Werz, O.3
  • 29
    • 0022406533 scopus 로고
    • Turnover of arachidonic acid in the major diacyl and ether phospholipids of human platelets
    • Purdon AD, Smith JB, (1985). Turnover of arachidonic acid in the major diacyl and ether phospholipids of human platelets. J Biol Chem 260: 12700-12704. (Pubitemid 16230557)
    • (1985) Journal of Biological Chemistry , vol.260 , Issue.23 , pp. 12700-12704
    • Purdon, A.D.1    Smith, J.B.2
  • 31
    • 77953526527 scopus 로고    scopus 로고
    • Microsomal prostaglandin e synthase-1 and 5-lipoxygenase: Potential drug targets in cancer
    • Radmark O, Samuelsson B, (2010). Microsomal prostaglandin E synthase-1 and 5-lipoxygenase: potential drug targets in cancer. J Intern Med 268: 5-14.
    • (2010) J Intern Med , vol.268 , pp. 5-14
    • Radmark, O.1    Samuelsson, B.2
  • 32
    • 34347397335 scopus 로고    scopus 로고
    • 5-Lipoxygenase: regulation of expression and enzyme activity
    • DOI 10.1016/j.tibs.2007.06.002, PII S0968000407001442
    • RÃ¥dmark O, Werz O, Steinhilber D, Samuelsson B, (2007). 5-Lipoxygenase: regulation of expression and enzyme activity. Trends Biochem Sci 32: 332-341. (Pubitemid 47021417)
    • (2007) Trends in Biochemical Sciences , vol.32 , Issue.7 , pp. 332-341
    • Radmark, O.1    Werz, O.2    Steinhilber, D.3    Samuelsson, B.4
  • 33
    • 77958464748 scopus 로고    scopus 로고
    • Discovery of potent and selective inhibitors of human reticulocyte 15-lipoxygenase-1
    • Rai G, Kenyon V, Jadhav A, Schultz L, Armstrong M, Jameson JB, et al,. (2010). Discovery of potent and selective inhibitors of human reticulocyte 15-lipoxygenase-1. J Med Chem 53: 7392-7404.
    • (2010) J Med Chem , vol.53 , pp. 7392-7404
    • Rai, G.1    Kenyon, V.2    Jadhav, A.3    Schultz, L.4    Armstrong, M.5    Jameson, J.B.6
  • 35
    • 33645241411 scopus 로고    scopus 로고
    • Affinity labeling of the rabbit 12/15-lipoxygenase using azido derivatives of arachidonic acid
    • Romanov S, Wiesner R, Myagkova G, Kühn H, Ivanov I, (2006). Affinity labeling of the rabbit 12/15-lipoxygenase using azido derivatives of arachidonic acid. Biochemistry 45: 3554-3562.
    • (2006) Biochemistry , vol.45 , pp. 3554-3562
    • Romanov, S.1    Wiesner, R.2    Myagkova, G.3    Kühn, H.4    Ivanov, I.5
  • 37
    • 0030033240 scopus 로고    scopus 로고
    • The effect of 5-lipoxygenase inhibition on Ascaris antigen (Ag)-induced responses in atopic monkeys
    • DOI 10.1007/BF02263504
    • Turner CR, Smith WB, Andresen CJ, Eggler JF, Watson JW, (1996). The effect of 5-lipoxygenase inhibition on Ascaris antigen (Ag)-induced responses in atopic monkeys. Inflamm Res 45: 42-49. (Pubitemid 26032105)
    • (1996) Inflammation Research , vol.45 , Issue.1 , pp. 42-49
    • Turner, C.R.1    Smith, W.B.2    Andresen, C.J.3    Eggler, J.F.4    Watson, J.W.5
  • 38
    • 0028031723 scopus 로고
    • Synthesis and biological evaluation of 5-[[3,5-bis(1,1-dimethylethyl)-4- hydroxyphenyl]methylene]oxazoles, -thiazoles, and -imidazoles: Novel dual 5- lipoxygenase and cyclooxygenase inhibitors with antiinflammatory activity
    • Unangst PC, Connor DT, Cetenko WA, Sorenson RJ, Kostlan CR, Sircar JC, et al,. (1994). Synthesis and biological evaluation of 5-[[3,5-bis(1,1- dimethylethyl)-4-hydroxyphenyl]methylene]oxazoles,-thiazoles, and -imidazoles: novel dual 5-lipoxygenase and cyclooxygenase inhibitors with antiinflammatory activity. J Med Chem 37: 322-328. (Pubitemid 24063052)
    • (1994) Journal of Medicinal Chemistry , vol.37 , Issue.2 , pp. 322-328
    • Unangst, P.C.1    Connor, D.T.2    Cetenko, W.A.3    Sorenson, R.J.4    Kostlan, C.R.5    Sircar, J.C.6    Wright, C.D.7    Schrier, D.J.8    Dyer, R.D.9
  • 39
    • 33750102847 scopus 로고    scopus 로고
    • Therapeutic options for 5-lipoxygenase inhibitors
    • DOI 10.1016/j.pharmthera.2006.05.009, PII S0163725806001070
    • Werz O, Steinhilber D, (2006). Therapeutic options for 5-lipoxygenase inhibitors. Pharmacol Ther 112: 701-718. (Pubitemid 44592614)
    • (2006) Pharmacology and Therapeutics , vol.112 , Issue.3 , pp. 701-718
    • Werz, O.1    Steinhilber, D.2
  • 40
    • 0029820419 scopus 로고    scopus 로고
    • Purification of transforming growth factor beta1 from human platelets
    • Werz O, Brungs M, Steinhilber D, (1996). Purification of transforming growth factor beta 1 from human platelets. Pharmazie 51: 893-896. (Pubitemid 26412712)
    • (1996) Pharmazie , vol.51 , Issue.11 , pp. 893-896
    • Werz, O.1    Brungs, M.2    Steinhilber, D.3
  • 41
    • 0031822546 scopus 로고    scopus 로고
    • Nonredox 5-lipoxygenase inhibitors require glutathione peroxidase for efficient inhibition of 5-lipoxygenase activity
    • Werz O, Szellas D, Henseler M, Steinhilber D, (1998). Nonredox 5-lipoxygenase inhibitors require glutathione peroxidase for efficient inhibition of 5-lipoxygenase activity. Mol Pharmacol 54: 445-451. (Pubitemid 28368835)
    • (1998) Molecular Pharmacology , vol.54 , Issue.2 , pp. 445-451
    • Werz, O.1    Szellas, D.2    Henseler, M.3    Steinhilber, D.4
  • 42
    • 0036719157 scopus 로고    scopus 로고
    • Extracellular signal-regulated kinases phosphorylate 5-lipoxygenase and stimulate 5-lipoxygenase product formation in leukocytes
    • Werz O, Bürkert E, Fischer L, Szellas D, Dishart D, Samuelsson B, et al,. (2002a). Extracellular signal-regulated kinases phosphorylate 5-lipoxygenase and stimulate 5-lipoxygenase product formation in leukocytes. FASEB J 16: 1441-1443.
    • (2002) FASEB J , vol.16 , pp. 1441-1443
    • Werz, O.1    Bürkert, E.2    Fischer, L.3    Szellas, D.4    Dishart, D.5    Samuelsson, B.6
  • 43
    • 0037177904 scopus 로고    scopus 로고
    • Arachidonic acid promotes phosphorylation of 5-lipoxygenase at Ser-271 by MAPK-activated protein kinase 2 (MK2)
    • DOI 10.1074/jbc.M111945200
    • Werz O, Szellas D, Steinhilber D, RÃ¥dmark O, (2002b). Arachidonic acid promotes phosphorylation of 5-lipoxygenase at Ser-271 by MAPK-activated protein kinase 2 (MK2). J Biol Chem 277: 14793-14800. (Pubitemid 34959961)
    • (2002) Journal of Biological Chemistry , vol.277 , Issue.17 , pp. 14793-14800
    • Werz, O.1    Szellas, D.2    Steinhilber, D.3    Radmark, O.4
  • 44
    • 0036464591 scopus 로고    scopus 로고
    • Activation of 5-lipoxygenase by cell stress is calcium independent in human polymorphonuclear leukocytes
    • DOI 10.1182/blood.V99.3.1044
    • Werz O, Bürkert E, Samuelsson B, RÃ¥dmark O, Steinhilber D, (2002c). Activation of 5-lipoxygenase by cell stress is calcium independent in human polymorphonuclear leukocytes. Blood 99: 1044-1052. (Pubitemid 34527142)
    • (2002) Blood , vol.99 , Issue.3 , pp. 1044-1052
    • Werz, O.1    Burkert, E.2    Samuelsson, B.3    Radmark, O.4    Steinhilber, D.5
  • 46
    • 0020462430 scopus 로고
    • 2,3,5-Trimethyl-6-(12-hydroxy-5,10-dodecadiynyl)-1,4-benzoquinone (AA861), a selective inhibitor of the 5-lipoxygenase reaction and the biosynthesis of slow-reacting substance of anaphylaxis
    • Yoshimoto T, Yokoyama C, Ochi K, Yamamoto S, Maki Y, Ashida Y, et al,. (1982). 2,3,5-Trimethyl-6-(12-hydroxy-5,10-dodecadiynyl)-1,4-benzoquinone (AA861), a selective inhibitor of the 5-lipoxygenase reaction and the biosynthesis of slow-reacting substance of anaphylaxis. Biochim Biophys Acta 713: 470-473. (Pubitemid 13222960)
    • (1982) Biochimica et Biophysica Acta , vol.713 , Issue.2 , pp. 470-473
    • Yoshimoto, T.1    Yokoyama, C.2    Ochi, K.3
  • 47
    • 0022002461 scopus 로고
    • Studies on thiazolin-4-one: Synthesis of some pyrano[2,3-b]thiazole derivatives
    • Zayed EM, Elbannany AAA, Ghozlan SAS, (1985). Studies on thiazolin-4-one: synthesis of some pyrano[2,3b]-thiazole derivatives. Pharmazie 40: 194-196. (Pubitemid 15124232)
    • (1985) Pharmazie , vol.40 , Issue.3 , pp. 194-196
    • Zayed, E.M.1    Elbannany, A.A.2    Ghozlan, S.A.S.3
  • 48
    • 0026567751 scopus 로고
    • Mutagenesis of some conserved residues in human 5-lipoxygenase: Effects on enzyme activity
    • Zhang YY, Radmark O, Samuelsson B, (1992). Mutagenesis of some conserved residues in human 5-lipoxygenase: effects on enzyme activity. Proc Natl Acad Sci U S A 89: 485-489.
    • (1992) Proc Natl Acad Sci U S A , vol.89 , pp. 485-489
    • Zhang, Y.Y.1    Radmark, O.2    Samuelsson, B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.