Multi-target approach for natural products in inflammation

Drug Discovery Today

Volumn 19, Issue 12, 2014, Pages 1871-1882

  Koeberle, Andreas ^a   Werz, Oliver ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLSALICYLIC ACID; ADENYLATE KINASE; ANTIINFLAMMATORY AGENT; ARACHIDONATE 5 LIPOXYGENASE; BOSWELLIC ACID; CURCUMIN; DIHYDROFOLATE REDUCTASE; DNA TOPOISOMERASE; EPIGALLOCATECHIN GALLATE; GLYCOGEN SYNTHASE KINASE 3BETA; HISTONE ACETYLTRANSFERASE; ICOSANOID; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INTERLEUKIN 1; LICOFELONE; LIPOXIN; NATURAL PRODUCT; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN E2; PROSTAGLANDIN SYNTHASE; PROTEASOME; PROTEIN KINASE B; PROTEIN KINASE C; PROTEIN P53; QUERCETIN; RESVERATROL; SALICYLIC ACID; TELOMERASE; TRANSCRIPTION FACTOR NRF2; TUMOR NECROSIS FACTOR ALPHA; BIOLOGICAL PRODUCT;

CYTOKINE PRODUCTION; DRUG SAFETY; DRUG SCREENING; INFLAMMATION; INNATE IMMUNITY; REVIEW; ANIMAL; HUMAN; METABOLISM; MOLECULARLY TARGETED THERAPY;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BIOLOGICAL PRODUCTS; HUMANS; INFLAMMATION; MOLECULAR TARGETED THERAPY;

EID: 84919352979     PISSN: 13596446     EISSN: 18785832     Source Type: Journal    
DOI: 10.1016/j.drudis.2014.08.006     Document Type: Review

References (110)

1. R. Medzhitov Origin and physiological roles of inflammation Nature 454 2008 428 435
2. R. Morphy, and Z. Rankovic Designed multiple ligands. An emerging drug discovery paradigm J. Med. Chem. 48 2005 6523 6543
3. W.L. Smith Enzymes of the cyclooxygenase pathways of prostanoid biosynthesis Chem. Rev. 111 2011 5821 5865
4. A. Straube Combined analgesics in (headache) pain therapy: shotgun approach or precise multi-target therapeutics? BMC Neurol. 11 2011 43
5. A.L. Harvey Natural products in drug discovery Drug Discov. Today 13 2008 894 901
6. K.D. Rainsford Anti-inflammatory drugs in the 21st century Subcell. Biochem. 42 2007 3 27
7. F. Celotti, and S. Laufer Anti-inflammatory drugs: new multitarget compounds to face an old problem. The dual inhibition concept Pharmacol. Res. 43 2001 429 436
8. A. Koeberle, and O. Werz Inhibitors of the microsomal prostaglandin E(2) synthase-1 as alternative to non steroidal anti-inflammatory drugs (NSAIDs) - a critical review Curr. Med. Chem. 16 2009 4274 4296
9. M.J. Stables, and D.W. Gilroy Old and new generation lipid mediators in acute inflammation and resolution Prog. Lipid Res. 50 2011 35 51
10. A. Koeberle Arachidonoyl-phosphatidylcholine oscillates during the cell cycle and counteracts proliferation by suppressing Akt membrane binding Proc. Natl. Acad. Sci. U. S. A. 110 2013 2546 2551
11. H.F. Cheng, and R.C. Harris Renal effects of non-steroidal anti-inflammatory drugs and selective cyclooxygenase-2 inhibitors Curr. Pharm. Des. 11 2005 1795 1804
12. P. McGettigan, and D. Henry Cardiovascular risk and inhibition of cyclooxygenase: a systematic review of the observational studies of selective and nonselective inhibitors of cyclooxygenase 2 JAMA 296 2006 1633 1644
13. O. Radmark, and B. Samuelsson Microsomal prostaglandin E synthase-1 and 5-lipoxygenase: potential drug targets in cancer J. Intern. Med. 268 2010 5 14
14. J.R. Vane Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs Nat. New Biol. 231 1971 232 235
15. G.J. Roth Acetylation of prostaglandin synthase by aspirin Proc. Natl. Acad. Sci. U. S. A. 72 1975 3073 3076
16. R. Amann, and B.A. Peskar Anti-inflammatory effects of aspirin and sodium salicylate Eur. J. Pharmacol. 447 2002 1 9
17. R. Morphy From magic bullets to designed multiple ligands Drug Discov. Today 9 2004 641 651
18. G.R. Zimmermann Multi-target therapeutics: when the whole is greater than the sum of the parts Drug Discov. Today 12 2007 34 42
19. R. Morphy, and Z. Rankovic Fragments, network biology and designing multiple ligands Drug Discov. Today 12 2007 156 160
20. M.H. Pang A series of case studies: practical methodology for identifying antinociceptive multi-target drugs Drug Discov. Today 17 2012 425 434
21. W. Gattrell Designed multiple ligands in metabolic disease research: from concept to platform Drug Discov. Today 18 2013 692 696
22. P. Csermely Structure and dynamics of molecular networks: a novel paradigm of drug discovery: a comprehensive review Pharmacol. Ther. 138 2013 333 408
23. K. Meirer Inhibitors of the arachidonic acid cascade: interfering with multiple pathways Basic Clin. Pharmacol. Toxicol. 114 2014 83 91
24. R. Jund Clinical efficacy of a dry extract of five herbal drugs in acute viral rhinosinusitis Rhinology 50 2012 417 426
25. M. Abdel-Tawab Boswellia serrata: an overall assessment of in vitro, preclinical, pharmacokinetic and clinical data Clin. Pharmacokinet. 50 2011 349 369
26. J.P. Raynauld Risk factors predictive of joint replacement in a 2-year multicentre clinical trial in knee osteoarthritis using MRI: results from over 6 years of observation Ann. Rheum. Dis. 70 2011 1382 1388
27. A. Koeberle Licofelone suppresses prostaglandin E2 formation by interference with the inducible microsomal prostaglandin E2 synthase-1 J. Pharmacol. Exp. Ther. 326 2008 975 982
28. L. Fischer The molecular mechanism of the inhibition by licofelone of the biosynthesis of 5-lipoxygenase products Br. J. Pharmacol. 152 2007 471 480
29. S.C. Karcher, and S.A. Laufer Successful structure-based design of recent p38 MAP kinase inhibitors Curr. Top. Med. Chem. 9 2009 655 676
30. E. Proschak Reconsidering the drug discovery pipeline for designed multitarget drugs Drug Discov. Today 18 2013 1129 1130
31. B. Over Natural-product-derived fragments for fragment-based ligand discovery Nat. Chem. 5 2013 21 28
32. J. Achenbach Exploring the chemical space of multitarget ligands using aligned self-organizing maps ACS Med. Chem. Lett. 4 2013 1169 1172
33. P. Csermely The efficiency of multi-target drugs: the network approach might help drug design Trends Pharmacol. Sci. 26 2005 178 182
34. A. Bender Analysis of pharmacology data and the prediction of adverse drug reactions and off-target effects from chemical structure ChemMedChem 2 2007 861 873
35. A. Koeberle SAR studies on curcumin's pro-inflammatory targets: discovery of prenylated pyrazolocurcuminoids as potent and selective novel inhibitors of 5-lipoxygenase J. Med. Chem. 57 2014 5638 5648
36. P.A. Clemons Complex phenotypic assays in high-throughput screening Curr. Opin. Chem. Biol. 8 2004 334 338
37. J.L. Medina-Franco Shifting from the single to the multitarget paradigm in drug discovery Drug Discov. Today 18 2013 495 501
38. D.S. Dumlao High-throughput lipidomic analysis of fatty acid derived eicosanoids and N-acylethanolamines Biochim. Biophys. Acta 1811 2011 724 736
39. J.L. Jenkins, and L. Urban Phenotypic screening: fishing for neuroactive compounds Nat. Chem. Biol. 6 2010 172 173
40. A. Koutsoukas From in silico target prediction to multi-target drug design: current databases, methods and applications J. Proteomics 74 2011 2554 2574
41. H. Lin A pharmacological organization of G-protein-coupled receptors Nat. Methods 10 2013 140 146
42. J. Besnard Automated design of ligands to polypharmacological profiles Nature 492 2012 215 220
43. T. Esatbeyoglu Curcumin - from molecule to biological function Angew. Chem. Int. Ed. Engl. 51 2012 5308 5332
44. D.K. Agrawal, and P.K. Mishra Curcumin and its analogues: potential anticancer agents Med. Res. Rev. 30 2010 818 860
45. J. Hong Modulation of arachidonic acid metabolism by curcumin and related beta-diketone derivatives: effects on cytosolic phospholipase A(2), cyclooxygenases and 5-lipoxygenase Carcinogenesis 25 2004 1671 1679
46. A. Koeberle Curcumin blocks prostaglandin E2 biosynthesis through direct inhibition of the microsomal prostaglandin E2 synthase-1 Mol. Cancer Ther. 8 2009 2348 2355
47. Y. Bustanji Inhibition of glycogen synthase kinase by curcumin: investigation by simulated molecular docking and subsequent in vitro/in vivo evaluation J. Enzyme Inhib. Med. Chem. 24 2009 771 778
48. A.L. Kasinski Inhibition of IkappaB kinase-nuclear factor-kappaB signaling pathway by 3,5-bis(2-flurobenzylidene)piperidin-4-one (EF24), a novel monoketone analog of curcumin Mol. Pharmacol. 74 2008 654 661
49. B.N. Singh Green tea catechin, epigallocatechin-3-gallate (EGCG): mechanisms, perspectives and clinical applications Biochem. Pharmacol. 82 2011 1807 1821
50. W. Yu Cellular and molecular effects of resveratrol in health and disease J. Cell. Biochem. 113 2012 752 759
51. M. Russo The flavonoid quercetin in disease prevention and therapy: facts and fancies Biochem. Pharmacol. 83 2012 6 15
52. A.L. Cheng Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions Anticancer Res. 21 2001 2895 2900
53. M. Iwasaki Plasma tea polyphenol levels and subsequent risk of breast cancer among Japanese women: a nested case-control study Breast Cancer Res. Treat. 124 2010 827 834
54. S.T. Fung Comparison of catechin profiles in human plasma and urine after single dosing and regular intake of green tea (Camellia sinensis) Br. J. Nutr. 109 2013 2199 2207
55. V.A. Brown Repeat dose study of the cancer chemopreventive agent resveratrol in healthy volunteers: safety, pharmacokinetics, and effect on the insulin-like growth factor axis Cancer Res. 70 2010 9003 9011
56. D.C. Nieman Effects of quercetin and EGCG on mitochondrial biogenesis and immunity Med. Sci. Sports Exerc. 41 2009 1467 1475
57. T.D. Warner Influence of plasma protein on the potencies of inhibitors of cyclooxygenase-1 and -2 FASEB J. 20 2006 542 544
58. V.C. de Boer Tissue distribution of quercetin in rats and pigs J. Nutr. 135 2005 1718 1725
59. R.A. Sharma Effects of dietary curcumin on glutathione S-transferase and malondialdehyde-DNA adducts in rat liver and colon mucosa: relationship with drug levels Clin. Cancer Res. 7 2001 1452 1458
60. G. Garcea Consumption of the putative chemopreventive agent curcumin by cancer patients: assessment of curcumin levels in the colorectum and their pharmacodynamic consequences Cancer Epidemiol. Biomark. Prev. 14 2005 120 125
61. K. Brune Biodistribution of salicylates: a clue to the understanding of some effects and side effects Agents Actions Suppl. 2 1977 163 177
62. A.R. Neves Resveratrol in medicinal chemistry: a critical review of its pharmacokinetics, drug-delivery, and membrane interactions Curr. Med. Chem. 19 2012 1663 1681
63. Y.C. Liang Inhibition of cyclin-dependent kinases 2 and 4 activities as well as induction of Cdk inhibitors p21 and p27 during growth arrest of human breast carcinoma cells by (-)-epigallocatechin-3-gallate J. Cell. Biochem. 75 1999 1 12
64. M.Z. Fang Tea polyphenol (-)-epigallocatechin-3-gallate inhibits DNA methyltransferase and reactivates methylation-silenced genes in cancer cell lines Cancer Res. 63 2003 7563 7570
65. Y.L. Lin, and J.K. Lin (-)-Epigallocatechin-3-gallate blocks the induction of nitric oxide synthase by down-regulating lipopolysaccharide-induced activity of transcription factor nuclear factor-kappaB Mol. Pharmacol. 52 1997 465 472
66. F. Yang The green tea polyphenol (-)-epigallocatechin-3-gallate blocks nuclear factor-kappa B activation by inhibiting I kappa B kinase activity in the intestinal epithelial cell line IEC-6 Mol. Pharmacol. 60 2001 528 533
67. S. Nam Ester bond-containing tea polyphenols potently inhibit proteasome activity in vitro and in vivo J. Biol. Chem. 276 2001 13322 13330
68. E. Navarro-Peran The antifolate activity of tea catechins Cancer Res. 65 2005 2059 2064
69. I. Naasani Telomerase inhibition, telomere shortening, and senescence of cancer cells by tea catechins Biochem. Biophys. Res. Commun. 249 1998 391 396
70. N. Oku Inhibitory effect of green tea polyphenols on membrane-type 1 matrix metalloproteinase, MT1-MMP Biol. Pharm. Bull. 26 2003 1235 1238
71. S.J. Berger Green tea constituent (-)-epigallocatechin-3-gallate inhibits topoisomerase I activity in human colon carcinoma cells Biochem. Biophys. Res. Commun. 288 2001 101 105
72. A. Koeberle Green tea epigallocatechin-3-gallate inhibits microsomal prostaglandin E(2) synthase-1 Biochem. Biophys. Res. Commun. 388 2009 350 354
73. J. Hong Effects of purified green and black tea polyphenols on cyclooxygenase- and lipoxygenase-dependent metabolism of arachidonic acid in human colon mucosa and colon tumor tissues Biochem. Pharmacol. 62 2001 1175 1183
74. J. Tome-Carneiro Resveratrol and clinical trials: the crossroad from in vitro studies to human evidence Curr. Pharm. Des. 19 2013 6064 6093
75. P.C. Hollman Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers Am. J. Clin. Nutr. 62 1995 1276 1282
76. I. Naasani Blocking telomerase by dietary polyphenols is a major mechanism for limiting the growth of human cancer cells in vitro and in vivo Cancer Res. 63 2003 824 830
77. S.R. Paludan Synergistic action of pro-inflammatory agents: cellular and molecular aspects J. Leukoc. Biol. 67 2000 18 25
78. Y. Li Neutrophil oxygen radical generation. Synergistic responses to tumor necrosis factor and mono/polyunsaturated fatty acids J. Clin. Invest. 97 1996 1605 1609
79. R. Morphy, and J. Harris Designing Multi-Target Drugs 2012 Royal Society of Chemistry
80. L. Costantino, and D. Barlocco Designed multiple ligands: basic research vs clinical outcomes Curr. Med. Chem. 19 2012 3353 3387
81. A. Pujol Unveiling the role of network and systems biology in drug discovery Trends Pharmacol. Sci. 31 2010 115 123
82. E. Balogun Curcumin activates the haem oxygenase-1 gene via regulation of Nrf2 and the antioxidant-responsive element Biochem. J. 371 2003 887 895
83. T. Choudhuri Curcumin induces apoptosis in human breast cancer cells through p53-dependent Bax induction FEBS Lett. 512 2002 334 340
84. C. Natarajan, and J.J. Bright Curcumin inhibits experimental allergic encephalomyelitis by blocking IL-12 signaling through Janus kinase-STAT pathway in T lymphocytes J. Immunol. 168 2002 6506 6513
85. K. Balasubramanyam Curcumin, a novel p300/CREB-binding protein-specific inhibitor of acetyltransferase, represses the acetylation of histone/nonhistone proteins and histone acetyltransferase-dependent chromatin transcription J. Biol. Chem. 279 2004 51163 51171
86. M. Hasmeda, and G.M. Polya Inhibition of cyclic AMP-dependent protein kinase by curcumin Phytochemistry 42 1996 599 605
87. M.H. Aziz Resveratrol-caused apoptosis of human prostate carcinoma LNCaP cells is mediated via modulation of phosphatidylinositol 3′-kinase/Akt pathway and Bcl-2 family proteins Mol. Cancer Ther. 5 2006 1335 1341
88. M. Holmes-McNary, and A.S. Baldwin Jr. Chemopreventive properties of trans-resveratrol are associated with inhibition of activation of the IkappaB kinase Cancer Res. 60 2000 3477 3483
89. C. Hope Low concentrations of resveratrol inhibit Wnt signal throughput in colon-derived cells: implications for colon cancer prevention Mol. Nutr. Food Res. 52 Suppl. 1 2008 52 61
90. T.C. Hsieh Regulation of p53 and cell proliferation by resveratrol and its derivatives in breast cancer cells: an in silico and biochemical approach targeting integrin alphavbeta3 Int. J. Cancer 129 2011 2732 2743
91. O. Werz Inhibition of 5-lipoxygenase product synthesis by natural compounds of plant origin Planta Med. 73 2007 1331 1357
92. B. Annabi Resveratrol targeting of carcinogen-induced brain endothelial cell inflammation biomarkers MMP-9 and COX-2 is Sirt1-independent Drug Target Insights 6 2012 1 11
93. S. Ulrich Peroxisome proliferator-activated receptor gamma as a molecular target of resveratrol-induced modulation of polyamine metabolism Cancer Res. 66 2006 7348 7354
94. K. Suzuki, and T. Koike Resveratrol abolishes resistance to axonal degeneration in slow Wallerian degeneration (WldS) mice: activation of SIRT2, an NAD-dependent tubulin deacetylase Biochem. Biophys. Res. Commun. 359 2007 665 671
95. A. Puissant Resveratrol promotes autophagic cell death in chronic myelogenous leukemia cells via JNK-mediated p62/SQSTM1 expression and AMPK activation Cancer Res. 70 2010 1042 1052
96. Z. Ungvari Resveratrol confers endothelial protection via activation of the antioxidant transcription factor Nrf2 Am. J. Physiol. Heart Circ. Physiol. 299 2010 H18 H24
97. J.A. Mitchell Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase Proc. Natl. Acad. Sci. U. S. A. 90 1993 11693 11697
98. J.A. Mitchell Sodium salicylate inhibits cyclo-oxygenase-2 activity independently of transcription factor (nuclear factor kappaB) activation: role of arachidonic acid Mol. Pharmacol. 51 1997 907 912
99. S.A. Hawley The ancient drug salicylate directly activates AMP-activated protein kinase Science 336 2012 918 922
100. M.H. Pillinger Modes of action of aspirin-like drugs: salicylates inhibit erk activation and integrin-dependent neutrophil adhesion Proc. Natl. Acad. Sci. U. S. A. 95 1998 14540 14545
101. P. Schwenger Sodium salicylate induces apoptosis via p38 mitogen-activated protein kinase but inhibits tumor necrosis factor-induced c-Jun N-terminal kinase/stress-activated protein kinase activation Proc. Natl. Acad. Sci. U. S. A. 94 1997 2869 2873
102. E. Kopp, and S. Ghosh Inhibition of NF-kappa B by sodium salicylate and aspirin Science 265 1994 956 959
103. B.N. Cronstein Salicylates and sulfasalazine, but not glucocorticoids, inhibit leukocyte accumulation by an adenosine-dependent mechanism that is independent of inhibition of prostaglandin synthesis and p105 of NFkappaB Proc. Natl. Acad. Sci. U. S. A. 96 1999 6377 6381
104. N. Gulati The antiproliferative effect of quercetin in cancer cells is mediated via inhibition of the PI3K-Akt/PKB pathway Anticancer Res. 26 2006 1177 1181
105. K.W. Lee Raf and MEK protein kinases are direct molecular targets for the chemopreventive effect of quercetin, a major flavonol in red wine Cancer Res. 68 2008 946 955
106. G.W. Peet, and J. Li IkappaB kinases alpha and beta show a random sequential kinetic mechanism and are inhibited by staurosporine and quercetin J. Biol. Chem. 274 1999 32655 32661
107. C.H. Park Quercetin, a potent inhibitor against beta-catenin/Tcf signaling in SW480 colon cancer cells Biochem. Biophys. Res. Commun. 328 2005 227 234
108. R.L. Wiseman Flavonol activation defines an unanticipated ligand-binding site in the kinase-RNase domain of IRE1 Mol. Cell 38 2010 291 304
109. R. Boly Quercetin inhibits a large panel of kinases implicated in cancer cell biology Int. J. Oncol. 38 2011 833 842
110. F. Casagrande, and J.M. Darbon Effects of structurally related flavonoids on cell cycle progression of human melanoma cells: regulation of cyclin-dependent kinases CDK2 and CDK1 Biochem. Pharmacol. 61 2001 1205 1215