Sulindac sulfide suppresses 5-lipoxygenase at clinically relevant concentrations

Cellular and Molecular Life Sciences

Volumn 67, Issue 5, 2010, Pages 797-806

  Steinbrink, Svenja D ^a   Pergola, Carlo ^b   Bühring, Ulrike ^b   George, Sven ^a   Metzner, Julia ^a   Fischer, Astrid S ^a   Häfner, Ann Kathrin ^a   Wisniewska, Joanna M ^a   Geisslinger, Gerd ^a   Werz, Oliver ^b   Steinhilber, Dieter ^a   Maier, Thorsten J ^a  

^a GOETHE UNIVERSITY   (Germany)

^b UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Cyclooxygenase; Leukocytes; Leukotrienes; Nsaids; Off target effect

Indexed keywords

3 [3 TERT BUTYLTHIO 1 (4 CHLOROBENZYL) 5 (2 QUINOLINYLMETHOXY) 2 INDOLYL] 2,2 DIMETHYLPROPIONIC ACID; 3 [3 TERT BUTYLTHIO 1 (4 CHLOROBENZYL) 5 ISOPROPYL 2 INDOLYL] 2,2 DIMETHYLPROPIONIC ACID; ARACHIDONATE 5 LIPOXYGENASE; CALCIMYCIN; DICLOFENAC; INDOMETACIN; LEUKOTRIENE; LIPOPOLYSACCHARIDE; N [3 (3 PHENOXYPHENYL)ALLYL]ACETOHYDROXAMIC ACID; SULINDAC; SULINDAC SULFIDE; SULINDAC SULFONE; ZILEUTON; 5-LIPOXYGENASE-ACTIVATING PROTEIN; ANTIINFLAMMATORY AGENT; ARACHIDONATE 5 LIPOXYGENASE ACTIVATING PROTEIN; CARRIER PROTEIN; DRUG DERIVATIVE; LIPOXYGENASE INHIBITOR; MEMBRANE PROTEIN;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG STRUCTURE; HUMAN; HUMAN CELL; IC 50; NEUTROPHIL; BIOLOGICAL MODEL; BLOOD; CELL FREE SYSTEM; DOSE RESPONSE; DRUG ANTAGONISM; DRUG EFFECT; DRUG SCREENING; ENZYMOLOGY; METABOLISM; OSMOLARITY; PROTEIN TRANSPORT;

ANTI-INFLAMMATORY AGENTS; ARACHIDONATE 5-LIPOXYGENASE; BLOOD; CARRIER PROTEINS; CELL-FREE SYSTEM; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; HUMANS; LIPOXYGENASE INHIBITORS; MEMBRANE PROTEINS; MODELS, BIOLOGICAL; NEUTROPHILS; OSMOLAR CONCENTRATION; PROTEIN TRANSPORT; SULINDAC;

EID: 77949879292     PISSN: 1420682X     EISSN: 14209071     Source Type: Journal    
DOI: 10.1007/s00018-009-0206-0     Document Type: Article

References (41)

1. Parente L, Perretti M (2003) Advances in the pathophysiology of constitutive and inducible cyclooxygenases: two enzymes in the spotlight. Biochem Pharmacol 65: 153-159 (Pubitemid 36015818)
2. Grosch S, Maier TJ, Schiffmann S, Geisslinger G (2006) Cyclooxygenase-2 (COX-2)-independent anticarcinogenic effects of selective COX-2 inhibitors. J Natl Cancer Inst 98: 736-747 (Pubitemid 43983297)
3. Haanen C (2001) Sulindac and its derivatives: a novel class of anticancer agents. Curr Opin Investig Drugs 2: 677-683
4. Davies NM, Watson MS (1997) Clinical pharmacokinetics of sulindac. A dynamic old drug. Clin Pharmacokinet 32: 437-459
5. Williams CS, Goldman AP, Sheng H, Morrow JD, DuBois RN (1999) Sulindac sulfide, but not sulindac sulfone, inhibits colo-rectal cancer growth. Neoplasia 1: 170-176
6. Goluboff ET (2001) Exisulind, a selective apoptotic antineo-plastic drug. Expert Opin Investig Drugs 10: 1875-1882
7. Funk CD (2001) Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 294: 1871-1875
8. Werz O, Steinhilber D (2006) Therapeutic options for 5-lipoxy-genase inhibitors. Pharmacol Ther 112: 701-718
9. Werz O, Burkert E, Samuelsson B, Radmark O, Steinhilber D (2002) Activation of 5-lipoxygenase by cell stress is calcium independent in human polymorphonuclear leukocytes. Blood 99: 1044-1052 (Pubitemid 34527142)
10. 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
11. Brungs M, Radmark O, Samuelsson B, Steinhilber D (1995) Sequential induction of 5-lipoxygenase gene expression and activity in Mono Mac 6 cells by transforming growth factor beta and 1, 25-dihydroxyvitamin D3. Proc Natl Acad Sci USA 92: 107-111
12. Werz O, Steinhilber D (1996) Selenium-dependent peroxidases suppress 5-lipoxygenase activity in B-lymphocytes and immature myeloid cells. The presence of peroxidase-insensitive 5-lipoxy-genase activity in differentiated myeloid cells. Eur J Biochem 242: 90-97 (Pubitemid 26386360)
13. Werz O, Klemm J, Samuelsson B, Radmark O (2001) Phorbol ester up-regulates capacities for nuclear translocation and phos-phorylation of 5-lipoxygenase in Mono Mac 6 cells and human polymorphonuclear leukocytes. Blood 97: 2487-2495 (Pubitemid 32291497)
14. Maier TJ, Tausch L, Hoernig M, Coste O, Schmidt R, Angioni C, Metzner J, Groesch S, Pergola C, Steinhilber D, Werz O, Geis-slinger G (2008) Celecoxib inhibits 5-lipoxygenase. Biochem Pharmacol 76: 862-872
15. Albert D, Zundorf I, Dingermann T, Muller WE, Steinhilber D, Werz O (2002) Hyperforin is a dual inhibitor of cyclooxygenase-1 and 5-lipoxygenase. Biochem Pharmacol 64: 1767-1775 (Pubitemid 35355728)
16. Surette ME, Palmantier R, Gosselin J, Borgeat P (1993) Lipo-polysaccharides prime whole human blood and isolated neutrophils for the increased synthesis of 5-lipoxygenase prod-ucts by enhancing arachidonic acid availability: involvement of the CD14 antigen. J Exp Med 178: 1347-1355 (Pubitemid 23277366)
17. Siemoneit U, Pergola C, Jazzar B, Northoff H, Skarke C, Jauch J, Werz O (2009) On the interference of boswellic acids with 5-lipoxygenase: mechanistic studies in vitro and pharmacological relevance. Eur J Pharmacol 606: 246-254
18. Rouzer CA, Ford-Hutchinson AW, Morton HE, Gillard JW (1990) MK886, a potent and specific leukotriene biosynthesis inhibitor blocks and reverses the membrane association of 5-lipoxygenase in ionophore-challenged leukocytes. J Biol Chem 265: 1436-1442 (Pubitemid 20048962)
19. Feißt C, Pergola C, Rakonjac M, Rossi A, Koeberle A, Dodt G, Hoffmann M, Hoernig C, Fischer L, Steinhilber D, Franke L, Schneider G, Radmark O, Sautebin L, Werz O (2009) Hyperforin is a novel type of 5-lipoxygenase inhibitor with high efficacy in vivo. Cell Mol Life Sci 66: 2759-2771
20. Fischer L, Hornig M, Pergola C, Meindl N, Franke L, Tanrikulu Y, Dodt G, Schneider G, Steinhilber D, Werz O (2007) The molecular mechanism of the inhibition by licofelone of the bio-synthesis of 5-lipoxygenase products. Br J Pharmacol 152: 471-480
21. Brideau C, Chan C, Charleson S, Denis D, Evans JF, Ford-Hutchinson AW, Fortin R, Gillard JW, Guay J, Guevremont D et al (1992) Pharmacology of MK-0591 (3-[l-(4-chlorobenzyl)-3-(t-butylthio)-5-(quinolin-2-yl-methoxy)- indol-2-yl]-2, 2-dime-thyl propanoic acid), a potent, orally active leukotriene biosynthesis inhibitor, Can J Physiol Pharmacol 70: 799-807
22. Werz O (2002) 5-lipoxygenase: cellular biology and molecular pharmacology. Curr Drug Targets Inflamm Allergy 1: 23-44
23. Radmark O, Werz O, Steinhilber D, Samuelsson B (2007) 5-Lipoxygenase: regulation of expression and enzyme activity. Trends Biochem Sci 32: 332-341
24. Costa D, Gomes A, Reis S, Lima JL, Fernandes E (2005) Hydrogen peroxide scavenging activity by non-steroidal anti-inflammatory drugs. Life Sci 76: 2841-2848 (Pubitemid 40460329)
25. Santos F, Teixeira L, Lucio M, Ferreira H, Gaspar D, Lima JL, Reis S (2008) Interactions of sulindac and its metabolites with phospholipid membranes: an explanation for the peroxidation protective effect of the bioactive metabolite. Free Radic Res 42: 639-650
26. Egan RW, Gale PH (1985) Inhibition of mammalian 5-lipoxy-genase by aromatic disulfides. J Biol Chem 260: 11554-11559
27. Riendeau D, Denis D, Choo LY, Nathaniel DJ (1989) Stimulation of 5-lipoxygenase activity under conditions which promote lipid peroxidation. Biochem J 263: 565-572 (Pubitemid 19254162)
28. Piazza GA, Alberts DS, Hixson LJ, Paranka NS, Li H, Finn T, Bogert C, Guillen JM, Brendel K, Gross PH, Sperl G, Ritchie J, Burt RW, Ellsworth L, Ahnen DJ, Pamukcu R (1997) Sulindac sulfone inhibits azoxymethane-induced colon carcinogenesis in rats without reducing prostaglandin levels. Cancer Res 57: 2909-2915
29. Soh JW, Weinstein IB (2003) Role of COX-independent targets of NSAIDs and related compounds in cancer prevention and treatment. Prog Exp Tumor Res 37: 261-285
30. Meade EA, Smith WL, DeWitt DL (1993) Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) iso-zymes by aspirin and other non-steroidal anti-inflammatory drugs. J Biol Chem 268: 6610-6614
31. Oshima M, Murai N, Kargman S, Arguello M, Luk P, Kwong E, Taketo MM, Evans JF (2001) Chemoprevention of intestinal polyposis in the Apcdelta 716 mouse by rofecoxib, a specific cyclooxygenase-2 inhibitor. Cancer Res 61: 1733-1740 (Pubitemid 34292612)
32. Duggan DE, Hooke KF, Hwang SS (1980) Kinetics of the tissue distributions of sulindac and metabolites. Relevance to sites and rates of bioactivation. Drug Metab Dispos 8: 241-246
33. Huls G, Koomstra JJ, Kleibeuker JH (2003) Non-steroidal anti-inflammatory drugs and molecular carcinogenesis of colorectal. carcinomas. Lancet 362: 230-232 (Pubitemid 36859943)
34. Meistrom LG, Bentrem DJ, Salabat MR, Kennedy TJ, Ding XZ, Strouch M, Rao SM, Witt RC, Ternent CA, Talamonti MS, Bell RH, Adrian TA (2008) Overexpression of 5-lipoxygenase in colon polyps and cancer and the effect of 5-LOX inhibitors in vitro and in a murine model. Clin Cancer Res 14: 6525-6530
35. Romano M, Claria J (2003) Cyclooxygenase-2 and 5-lipoxyge-nase converging functions on cell proliferation and tumor angiogenesis: implications for cancer therapy. FASEB J 17: 1986-1995 (Pubitemid 37392443)
36. Rainsford KD (1977) The comparative gastric ulcerogenic activities of non-steroid anti-inflammatory drugs. Agents Actions 7: 573-577
37. Rainsford KD (1993) Leukotrienes in the pathogenesis of NSAID-induced gastric and intestinal mucosal damage. Agents Actions 39(Spec No): C24-C26
38. Cronstein BN, Terkeltaub R (2006) The inflammatory process of gout and its treatment. Arthritis Res Ther 8(Suppl 1): S3
39. Serhan CN, Lundberg U, Weissmann G, Samuelsson B (1984) Formation of leukotrienes and hydroxy acids by human neutro-phils and platelets exposed to monosodium urate. Prostaglandins 27: 563-581 (Pubitemid 14115760)
40. Ford-Hutchinson AW, Gresser M, Young RN (1994) 5-Lipoxy-genase. Annu Rev Biochem 63: 383-417
41. 41. Werz O, Steinhilber D (2005) Development of 5-lipoxygenase inhibitors-lessons from cellular enzyme regulation. Biochem Pharmacol 70: 327-333 (Pubitemid 40908906)