Current progress in antifibroitcs

Current Medicinal Chemistry

Volumn 18, Issue 20, 2011, Pages 3082-3092

  El Bialy, S A A ^a,c   Abd El Kader, K F ^b   El Ashmawy, M B ^b  

^a University of Mansoura   (Egypt)

^b MANSOURA UNIVERSITY   (Egypt)

^c GEORGIA STATE UNIVERSITY   (United States)

Author keywords

Antifibrotics; Cirrhosis; Epigenetic therapy; Extracellular matrix accumulation; Fibrogenesis; Fibrogenesis inhibitors; Fibrogenesis triggers; Fibrosis; Hepatic stellate cells (HSC); MMPs; Prolyl 4 hydroxylase

Indexed keywords

ANTIFIBROTIC AGENT; AZATHIOPRINE; CAMOSTAT MESILATE; CILOSTAZOL; COLLAGEN; CURCUMIN; CYCLOOXYGENASE 2 INHIBITOR; DARUSENTAN; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; GADOLINIUM CHLORIDE; HALOFUGINONE; HYDROXYBENZOIC ACID; IMATINIB; LEFLUNOMIDE; LOSARTAN; LUFIRONIL; MATRIX METALLOPROTEINASE; METADOXINE; N (2 CYCLOHEXYLOXY 4 NITROPHENYL)METHANESULFONAMIDE; PENTOXIFYLLINE; PIRFENIDONE; PREDNISONE; PROCOLLAGEN PROLINE 2 OXOGLUTARATE 4 DIOXYGENASE; SILIBININ; TERIFLUNOMIDE; TILMACOXIB; TRICHOSTATIN A; VORINOSTAT; ZINC CHLORIDE;

ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; AUTOIMMUNE HEPATITIS; BILIARY TRACT FIBROSIS; CELL ACTIVATION; CELL PROLIFERATION; COLLAGEN SYNTHESIS; CYTOKINE PRODUCTION; DRUG INHIBITION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; EPIGENETICS; EXTRACELLULAR MATRIX; FIBROGENESIS; FIBROSIS; HUMAN; LIPID PEROXIDATION; LIVER FIBROSIS; LUNG FIBROSIS; NONHUMAN; REVIEW; STELLATE CELL; UPREGULATION; ANIMAL; DRUG DEVELOPMENT; DRUG EFFECT; LIVER; LIVER CIRRHOSIS; PATHOLOGY;

ANIMALS; DRUG DISCOVERY; HUMANS; LIVER; LIVER CIRRHOSIS;

EID: 79959923753     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986711796391679     Document Type: Review

References (77)

1. Guzman, G. Overview of Liver Pathology. DM-Dis. Mon., 2008, 54, 419-431. (Pubitemid 351822329)
2. Friedman S. L. Liver fibrosis - from bench to bedside. J. Hepatol, 2003, 38, S38-S53.
3. Thorgeirsson, S. S.; Grisham, J. W. Molecular pathogenesis of human hepatocellular carcinoma. Nat. Genet, 2002, 31, 339-346. (Pubitemid 35154440)
4. Angelico, M.; Renganathan, E.; Gandin, C.; Fathy, M.; Profili, C.; Refai, W.; De Santis, A.; Nagi, A.; Amin, G.; Capocaccia, L.; Callea, F.; Rapicetta, M.; Badr, G.; Rocchi, G. Chronic liver disease in the Alexandria governorate, Egypt: contribution of Schistosomiasis and hepatitis virus infections. J. Hepatol, 1997, 26, 236-243. (Pubitemid 27077419)
5. Issa, R; Williams, E.; Trim, N.; Kendall, T.; Arthur, M. J.; Reichen, J.; Benyon, R. C.; Iredale, J. P. Apoptosis of hepatic stellate cells: involvement in resolution of biliary fibrosis and regulation by soluble growth factors. Gut, 2001, 48, 548-557. (Pubitemid 32234801)
6. Dufour, J. F.; DeLellis, R; Kaplan, M. Reversibility of hepatic fibrosis in autoimmune hepatitis. J. Ann. Intern. Med., 1997, 127, 981-985. (Pubitemid 27516609)
7. Hammel, P.; Couvelard, A.; O'Toole, D.; Ratouis, A.; Sauvanet, A.; Flejou, J. F.; Degott, C.; Belghiti, J.; Bernades, P.; Valla, D.; Ruszniewski, P.; Levy, P. Regression of liver fibrosis after biliary drainage in patients with chronic pancreatitis and stenosis of the common bile duct. N Engl J. Med., 2001, 344, 418-423. (Pubitemid 32128674)
8. Friedman, S. L. Mechanisms of Hepatic Fibrogenesis. Gastroenterology, 2008, 134, 1655-1669. (Pubitemid 351615417)
9. Cheng, J.; Imanishi, H.; Liu, W.; Iwasaki, A.; Ueki, N.; Nakamura, H.; Hada, T. Inhibition of the expression of α-smooth muscle actin in human hepatic stellate cell line, LI90, by a selective cyclooxygenase II inhibitor, NS-398. Biochem. Bioph. Res. Commun., 2000, 297, 1128-1134. (Pubitemid 35216365)
10. Yamamoto, H.; Kondo, M.; Nakamori, S.; Nagano, H.; Wakasa, K.; Sugita, Y.; Chang-de, J.; Kobayashi, S.; Damdinsuren, B.; Dono, K.; Umeshita, K.; Sekimoto, M.; Sakon, M.; Matsuura, N.; Monden, M. JTE-522, a cyclooxygenase-2 inhibitor, is an effective chemopreventive agent against rat experimental liver fibrosis. Gastroenterology, 2003, 125, 556-571. (Pubitemid 36929437)
11. Yu, J.; Wu, C. W.; Chu, E. S. H.; Hui, A. Y.; Cheng, A. S. L.; Go, M. Y. Y.; Ching, A. K. K.; Chui, Y. L.; Chan, H. L. Y; Sung, J. J. Y. Elucidation of the role of COX-II in liver fibrogenesis using transgenic mice. Biochem. Biophys. Res. Commun., 2008, 372, 571-577.
12. 3 treatment or dietary glycine. Am. J. Physiol Gastrointest. Liver Physiol, 2001, 281, 200-207.
13. Liu, C.; Crawford, J. M. In: Liver Anatomy; Encyclopedia of gastroenterology, Ed.; Elsevier: USA, 2004, pp. 510-515.
14. Friedman, S. L. Seminars in medicine of the Beth Israel Hospital, Boston. The cellular basis of hepatic fibrosis. Mechanisms and treatment strategies. N Engl J. med, 1993, 328, 1828-1835. (Pubitemid 23174715)
15. Friedman, S. L. Molecular Regulation of Hepatic Fibrosis, an Integrated Cellular Response to Tissue Injury. J. Biol Chem., 2000, 275, 2247-2250. (Pubitemid 30081976)
16. Olaso, E.; Friedman, S. L. Molecular regulation of hepatic fibrogenesis. J. Hepatol, 1998, 29, 836-847. (Pubitemid 28505945)
17. Friedman, S. L.; Yamasaki, G.; Wong, L. Modulation of Transforming Growth Factor β Receptors of Rat Lipocytes during the Hepatic Wound Healing Response. J. Biol Chem., 1994, 269, 10551-10558.
18. Muddu, A. K.; Guha, I. N.; Elsharkawy, A. M.; Mann, DA. Resolving fibrosis in the diseased liver: Translating the scientific promise to the clinic. Int. J. Biochem. Cell Biol, 2007, 39, 695-714. (Pubitemid 46366796)
19. Hung, K. S.; Lee, T. H.; Chou, W. Y; Wu, C. L.; Cho, C. L.; Lu, C. N.; Jawan, B.; Wang, C. H. Interleukin-10 gene therapy reverses thioacetamide- induced liver fibrosis in mice. Biochem. Biophys. Res. Commun., 2005, 336, 324-331. (Pubitemid 41253437)
20. Houglum, K.; Lee, K. S.; Chojkier, M. Proliferation of Hepatic Stellate Cells Is Inhibited by Phosphorylation of CREB on Serine 133. J. Clin. Invest, 1997, 99, 1322-1328. (Pubitemid 27142770)
21. Yoshiji, H.; Noguchi, R; Kuriyama, S.; Ikenaka, Y; Yoshii, J.; Yanase, K.; Namisaki, T; Kitade, M.; Masaki, T.; Fukui, H. Imatinib mesylate (STI-571) attenuates liver fibrosis development in rats. Am. J. Physiol Gastrointest. Liver Physiol, 2005, 288, G907-G913. (Pubitemid 40563130)
22. Xiong, X. A process for preparing N-(4-methyl-3-nitrophenyl)-4- formylbenzamide and its derivatives. CN Patent 101, 654, 416, February 24, 2010.
23. Desmoulière, A.; Xu, G.; Costa, A. M. A.; Yousef, I. M.; Gabbiani, G.; Tuchweber, B. Effect of pentoxifylline on early proliferation and phenotypic modulation of fibrogenic cells in two rat models of liver fibrosis and on cultured hepatic stellate cells. J. Hepatol, 1999, 30, 621-631. (Pubitemid 29151903)
24. Peterson, T. C.; Isbrucker, R. A.; Hooper, M. L. In vitro effect of Plateletderived growth factor on fibroproliferation and effect of cytokine antagonists. Immunopharmacology, 1994, 28, 259-270. (Pubitemid 24316902)
25. Gutiérrez-Ruiz, M. C.; Bucio, L.; Correa, A.; Souza, V.; Hernández, E.; Gómez-Quiroz, L. E.; Kershenobich, D. Metadoxine Prevents damage produced by ethanol and acetaldehyde in hepatocytes and hepatic stellate cells in culture. Pharmacol Res., 2001, 44, 431-436 (Pubitemid 33105083)
26. Zheng, S.; Yumei, F.; Chen, A. De novo synthesis of glutathione is a prerequisite for curcumin to inhibit hepatic stellate cell (HSC) activation. Free Rdical Biol Med., 2007, 43, 444-453. (Pubitemid 46977625)
27. Trappoliere, M.; Caligiuri, A.; Schmid, M.; Bertolani, C.; Failli, P.; Vizzutti, F.; Novo, E.; Di Manzano, C.; Marra, F; Loguercio, C.; Pinzani, M. Silybin, a component of sylimarin, exerts anti-inflammatory and anti-fibrogenic effects on human hepatic stellate cells. J. Hepatol, 2009, 50, 1102-1111.
28. Szuster-Ciesielska, A.; Plewka, K.; Daniluk, J.; Kandefer- Szerszeń, M. Zinc supplementation attenuates ethanol-and acetaldehyde-induced liver stellate cell activation by inhibiting reactive oxygen species (ROS) production and by influencing intracellular signaling. Biochem. Pharmacol, 2009, 78, 301-314.
29. Shimizu, E.; Kobayashi, Y.; Oki, Y.; Kawasaki, T.; Yoshimi, T.; Nakamura, H. OPC-13013, A Cyclic nucleotide phosphodiesterase type III inhibitor, Inhibits cell proliferation and trandifferentiation of cultured rat hepatic stellate cells. Life Sci., 1999, 64, 2081-2088. (Pubitemid 29236568)
30. Yamamoto, A.; Fukuyama, N.; Okaichi, Y.; Yamada, Y.; Miyamoto, H.; Tominaga, M. Progress for production Cilostazol. U. S. Patent 7, 026, 486 B2, April 11, 2006.
31. Okuno, M.; Akita, K.; Moriwaki, H.; Kawada, N.; Ikeda, K.; Kaneda, K.; Suzuki, Y; Kojima, S. Prevention of rat hepatic fibrosis by the protease inhibitor, Camostat Mesilate, via reduced generation of active TGF-b. Gastroenterology, 2001, 120, 1784-1800. (Pubitemid 32523496)
32. Hideki, S. New production method of Camostat Mesylate. J. P Patent 9, 309, 873, A, December 2, 1997.
33. Cho, J. J.; Hocher, B.; Herbst, H.; Jia, J. D.; Ruehl, M.; Hahn, E. G.; Riecken, E. O.; Schuppan, D. An oral endothelin-A receptor antagonist blocks collagen synthesis and deposition in advanced rat liver fibrosis. Gastroenterology, 2000, 118, 1169-1178. (Pubitemid 30346994)
34. a) Riechers, H.; Klinge, D.; Amberg, W.; Kling, A.; Muller, S.; Baumann, E.; Rheinheimer, J.; Vogelbacher, U. J.; Wernet, W.; Unger, L.; Raschack, M. Carboxylic acid derivatives, their preparation and their use. J. Med. Chem. 1996, 39, 2123-2128. b) US. Patent 7, 119, 097 B2, October 10, 2006.
35. Croquet, V.; Moal, F; Veal, N.; Wang, J.; Oberti, F; Roux, J.; Vuillemin, E.; Gallois, Y; Douay, O.; Chappard, D.; Cales, P. Hemodynamic and antifibrotic effects of losartan in rats with liver fibrosis and/or portal hypertension. J. Hepatol, 2002, 37, 773-780. (Pubitemid 35404216)
36. Deo, K.; Desai, S.; Rathod, D.; Parich, C; Mokal, R. An improved process for preparing losartan potassium. WO Patent 029457 A2, March 18, 2010.
37. Yoshiji, H.; Yoshii, Y; Ikenaka, Y; Noguchi, R; Tsujinoue, H.; Nakatani, T.; Imazu, H.; Yanase, K.; Kuriyama, S.; Fukui, H. Inhibition of reninangiotensin system attenuates liver enzyme-altered preneoplastic lesions and fibrosis development in rats. J. Hepatol, 2002, 37, 22-30. (Pubitemid 34713051)
38. Joshi, N, S.; Bhirud, S., B.; Rao, K. E.; Buddhavarapu, P. R; Soni, V. Process for the prepartiono of perindopril. U. S. Patent 2008, 0071, 094 A1, March 20, 2008.
39. Tang, X.; Yang, J.; Li, J. Accelerative effect of leflunomide on recovery from hepatic fibrosis involves TRAIL-mediated hepatic stellate cell apoptosis. Life Sci., 2009, 84, 552-557.
40. Fu, Y; Zhang, D. Q.; Jiang, S. H.; Du, Y. F.; Ren, YX. Synthesis of leflunomide Zhongguo Yiyao Gongye Zazhi. 2000, 31, 533-534.
41. Azuma, A.; Usuki, J. Novel therapy for idiopathic pulmonary fibrosis - How to evaluate the efficacy? Respir. Med. CME 2008, 1, 75-81.
42. Di Sario, A.; Bendia, E.; Baroni, G. S.; Ridolfi, F.; Casini, A.; Ceni, E.; Saccomanno, S.; Marzioni, M.; Trozzi, L.; Sterpetti, P.; Taffetani, S.; Benedetti, A. Effect of pirfenidone on rat hepatic stellate cell proliferation and collagen production. J. Hepatol, 2002, 37, 584-591. (Pubitemid 35305537)
43. Di Sario, A.; Bendia, E.; Macarri, G.; Candelaresi, C; Taffetani, S.; Marzioni, M.; Omenetti, A.; De Minicis, S.; Trozzi, L.; Benedetti, A. The anti-fibrotic effect of pirfenidone in rat liver fibrosis is mediated by downregulation of procollagen a1 (I), TIMP-1 and MMP-2. Digest. Liver Dis., 2004, 36, 744-751. (Pubitemid 41070596)
44. Salazar-Montes, A.; Ruiz-Corro, L.; López-Reyes, A.; Castrejón-Gómez, E.; Armendáriz-Borunda, J. Potent antioxidant role of Pirfenidone in experimental cirrhosis. Eur. J. Pharmacol, 2008, 595, 69-77.
45. Magana C; Jose A. R.; Vazquez C. L.; Armendariz B., Juan S. New process of synthesis for obtaining 5-methyl-1-phenyl-2-(1H)-pyridone, compositions and use thereof as cytoprotective and dermatological agent in topical applications. WO patent 2008/147170 A1, December 4, 2008.
46. Myllyharju, J. Prolyl 4-hydroxylases, the key enzymes of collagen biosynthesis. Matrix Biol, 2003, 22, 15-24. (Pubitemid 36444503)
47. Matsumura, Y; Sakaida, I; Uchida, K.; Kimura, T.; Ishihara, T.; Okita, K. Prolyl 4-hydroxylase inhibitor (HOE 077) inhibits pig serum-induced rat liver fibrosis by preventing stellate cell activation. J. Hepatol, 1997, 27, 185-192. (Pubitemid 27357075)
48. Spira, G.; Mawasi, N; Paizi, M.; Anbinder, N; Genina, O.; Alexiev, R.; Pines, M. Halofuginone, a collagen type I inhibitor improves liver regeneration in cirrhotic rats. J. Hepatol, 2002, 37, 331-339. (Pubitemid 34969949)
49. Wolffe, A. P; Matzke, M. A. Epigenetics: regulation through repression. Science, 1999, 286, 481-486.
50. Myllyharju, J.; Kivirikko, K. I. Collagens, modifying enzymes and their mutations in humans, flies and worms. Trends Genet, 2004, 20, 33-43. (Pubitemid 38032818)
51. Gelse, K.; Poschl, E.; Aigner, T. Collagens-structure, function, and biosynthesis. Adv. Drug Deliv. Rev, 2003, 55, 1531-1546.
52. Tandon, M.; Wu, M.; Begley, T. P. Substrate specificity of human prolyl-4-hydroxylase. Bioorg Med. Chem. Lett, 1998, 8, 1139-1144. (Pubitemid 28231386)
53. Hanauask-Abel, HM. Prolyl 4hydroxylase, a target enzyme for drug development; Design of suppressive agents and the in vitro effects of inhibitors and proinhibitors. J. Hepatol, 1991, 13, 8-16
54. Kivirikko, K. I.; Myllyharju, J. Prolyl 4-hydroxylases and their protein disulfide isomerase subunit. Matrix. Biol, 1998, 16, 357-368. (Pubitemid 28069862)
55. Annunen, P.; Helaakoski, T.; Myllyharju, J.; Veijola, J.; Pihlajaniemi, T.; Kivirikko, K. I. Cloning of the human prolyl 4-hydroxylase α subunit isoform a (II) and characterization of the type II enzyme tetramer. The α (I) and α (II) subunits do not form a mixed α (I) α (II) β2 tetramer. J. Biol Chem., 1997, 272, 17342-17348. (Pubitemid 27311159)
56. Kukkola, L.; Hieta, R; Kivirikko, K. I.; Myllyharju, J. Identification and characterization of a third human, rat and mouse collagen prolyl 4 hydroxylase isoenzyme. J. Biol Chem., 2003, 278, 47685-47693. (Pubitemid 37523214)
57. Kivirikko, K. I.; Myllylä, R; Pihlajaniemi, T. Protein hydroxylation: prolyl 4hydroxylase, an enzyme with four co-substrates and a multifunctional subunit. FASEB J., 1989, 3, 1609-1617.
58. Günzler, V; Brocks, D.; Henke, S.; Myllylä, R; Geiger, R; Kivirikko, K. I. Syncatalytic inactivation of prolyl 4-hydroxylase by synthetic peptides containing the unphysiologic amino acid 5-oxaproline. J. Biol Chem., 1988, 263, 19498-19504. (Pubitemid 19016428)
59. Majamaa, K.; Günzler, V; Hanauske Abel, H.; Myllylä, R; Kivirikko, K. I. Partial Identity of the 2-oxoglutarate and ascorbate binding sites of prolyl 4-hydroxylase. J. Biol Chem., 1986, 261, 7819-7823. (Pubitemid 17208708)
60. Wang, J.; Buss, J. L.; Chen, G.; Ponka, P.; Pantopoulos, K. The prolyl 4-hydroxylase inhibitor ethyl-3, 4-dihydroxybenzoate generates effective iron deficiency in cultured cells. FEBS Lett, 2002, 529, 309-312.
61. Bickel, M.; Brocks, D.; Burghard, H.; Gunzler, V.; Henke, S.; Hanauske-Abel, H.; Mohr, J.; Tschank, G. Pyridine-2, 4-and-2, 5-dicarboxylic acid amides and medicaments based on these compounds. U. S. Patent 5, 037, 839, August 6, 1991.
62. Hemmann, S.; Graf, J.; Roderfeld, M.; Roeb, E. Expression of MMPs and TIMPs in liver fibrosis - a systematic review with special emphasis on antifibrotic strategies. J. Hepatol, 2007. 46, 955-975. (Pubitemid 46529049)
63. Verma, R. P; Hansch, C. Matrix metalloproteinases (MMPs): Chemicalbiological functions and (Q) SARs. Bioorg. Med. Chem., 2007, 15, 2223-2268. (Pubitemid 46240907)
64. Arthur, M. J. P Metalloproteinases and their inhibitors in liver fibrosis. Am. J. Physiol Gastrointest. Liver Physiol, 2000, 279, 245-249.
65. Roderfeld, M.; Weiskirchen, R.; Wagner, S.; Berres, M. L.; Henkel, C; Grotzinger, J.; Gressner, A. M.; Matern, S.; Roeb, E. Inhibition of hepatic fibrogenesis by matrix metalloproteinase-9 mutants in mice. FASEB J., 2006, 20, 444-454. (Pubitemid 44933321)
66. Wells, R. G. Mechanisms of liver fibrosis: New insights into an old problem. Drug. Discov. Today Dis. Mech, 2006, 3, 489-495.
67. Schuppan, D.; Porov, Y. Hepatic fibrosis: From bench to bedside. J. Gastroenterol Hepatol, 2002, 17, 300-305.
68. Popov, Y; Patsenker, E.; Bauer, M.; Niedobitek, E.; Schulze-Krebs, A. Halofuginone Induces Matrix Metalloproteinases in Rat Hepatic Stellate Cells via Activation of p38 and NFκB. J. Biol Chem., 2006, 281, 15090-15098. (Pubitemid 43855098)
69. Mao, Z. X.; Mao, G. X.; Jin, J. T.; Huang, W. B. Preparation of halofuginone hydrobromide. C. N. Patent, 1651428, A, August 10, 2005.
70. Erez, M.; Halevi, K. Pharmaceutical compositions of the isolated D-enantiomer of the quinazolinone derivative Halofuginone. U. S. Patent 0, 255, 165, A1, October 16, 2008.
71. Linder, M. R.; Heckeroth, A. R.; Najdrowski, M.; Daugschies, A.; Schollmeyer, D.; Miculka, C. (2R, 3S) - (+) - and (2S, 3R) - (-)-Halofuginone lactate: Synthesis, absolute configuration, and activity against Cryptosporidium parvum. Bioorg. Med. Chem. Lett., 2007, 17, 4140-4143. (Pubitemid 47028605)
72. Ganesan, A.; Nolan, L.; Crabb, S. J.; Packham, G. Epigenetic therapy: histone acetylation, DNA methylation and anti-cancer drug discovery. Curr. Cancer Drug Targets, 2009, 9, 963-981.
73. Wang, Z.; Chen, C.; Finger, S. N.; Shaqireen D/O K. M. M.; Jung, M.; Schwarz, H.; Swanson, N.; Laureu, R. R.; Raghunath, M. Suberoylanilide hydroxamic acid-a potential epigenetic therapeutic agent for lung fibrosis? Eur. Resp J., 2009, 34, 145-155.
74. Chen, C. Z. C; Peng, Y. X.; Wang, Z. B; Fish, P. V.; Kaar, J. L.; Koepsel, R. R.; Russell, A. J.; Laureu, R. R.; Raghunath, M. The Scar-in-a-Jar: studying potential antifibrotic compounds from the epigenetic to extracellular level in a single well. Br. J. Pharmacol., 2009, 158, 1196-1209.
75. Galtonde, A.; Choudhari, B. Novel process for the preparation of Vorinostat. U. S. Patent 2011/0039937 A1, February 17, 2011.
76. Rombouts, K.; Niki, T.; Greenwel, P.; Vandermonde, A.; Wielant, A.; Hellemans, K.; De Bleser, P.; Yoshida, M.; Schuppan, D.; Rojkind, M.; Geerts, A. Trichostatin A, a histone deacetylase inhibitor, suppresses collagen synthesis and prevents TGF-beta (1)-induced fibrogenesis in skin fibroblasts. Exp. Cell. Res., 2002, 278, 184-197. (Pubitemid 35002103)
77. Helquist, P.; Löfstedt, J. Process for preparing histone deacylase inhibitors and intermediate thereof. U. S. Patent 7, 235, 688 B1, June 26, 2007.