Matrix metalloproteinase inhibitors (MMPIs) from marine natural products: The current situation and future prospects

Marine Drugs

Volumn 7, Issue 2, 2009, Pages 71-84

  Zhang, Chen ^a   Kim, Se Kwon ^a  

^a Pukyong National University   (South Korea)

Author keywords

AP 1.; Marine natural products; Matrix metalloproteinase inhibitors (MMPIs); Matrix metalloproteinases (MMPs); NF B; Tissue inhibitors of metalloproteinase (TIMPs)

Indexed keywords

3 (3,4 DIHYDROXYPHENYL)ACRYLIC ACID PHENETHYL ESTER; 3 O BETA DEXTRO GLUCOSIDE DERIVATIVE; BACTERIAL ENZYME; CAFFEIC ACID PHENETHYL ESTER; CARBOXYLATED CHITOOLIGOSACCHARIDE; CHITOOLIGOSACCHARIDE 1; CHITOSE OLIGOSACCHARIDE; COLLAGENASE 1; FATTY ACID; FLAVONOID GLYCOSIDE; FUCOIDIN; GELATINASE A; GELATINASE B; GLYCOSAMINOGLYCAN; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INTERSTITIAL COLLAGENASE; ISORHAMNETIN; LAMBDA CARRAGEENAN OLIGOSACCHARIDE; MATRIX METALLOPROTEINASE; MATRIX METALLOPROTEINASE INHIBITOR; PHLOROTANNIN; POLYPHENOL DERIVATIVE; POLYSACCHARIDE SULFATE; QUERCETIN; SACCHARIN; SULFATED GLUCOSAMINE; TRANSCRIPTION FACTOR AP 1; UNCLASSIFIED DRUG; UNINDEXED DRUG; VASCULOTROPIN;

ANGIOGENESIS; ARTHRALGIA; ARTHRITIS; CHRONIC INFLAMMATION; CONCENTRATION RESPONSE; DOWN REGULATION; DRUG MECHANISM; ENDOTHELIUM CELL; ENZYME ACTIVITY; ENZYME INHIBITION; GENE EXPRESSION; GROWTH INHIBITION; HUMAN; MARINE SPECIES; METASTASIS; NONHUMAN; PROTEIN EXPRESSION; PROTEIN SYNTHESIS INHIBITION; REVIEW; SHRIMP; WRINKLE;

EID: 66449084700     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md7020071     Document Type: Review

References (68)

1. Sternlicht, M.D.; Werb, Z. How matrix metalloproteinases regulate cell behavior. Annu. Rev. Cell. Dev. Biol. 2001, 17, 463-516.
2. Sang, Q.X.; Jin, Y.; Newcomer, R.G.; Monroe, S.C.; Fang, X.X.; Hurst, D.R.; Lee, S.; Cao, Q.; Schwartz, M.A. Matrix metalloproteinase inhibitors as prospective agents for the prevention and treatment of cardiovascular and neoplastic diseases. Curr. Top. Med. Chem. 2006, 6, 289-316.
3. Hu, J.L.; Van den Steen, P.E.; Sang, Q.X.; Opdenakker, G. Matrix metalloproteinase inhibitors as therapy for inflammatory and vascular diseases. Nat. Rev. Drug Discov. 2007, 6, 480-498.
4. Egeblad, M.; Werb, Z. New functions for the matrix metalloproteinase in cancer progression. Nat. Rev. Cancer 2002, 2, 161-174.
5. Overall, C.M.; Lopez-Otin, C. Strategies for MMP inhibition in cancer: innovations for the post-trial era. Nat. Rev. Cancer 2002, 2, 657-672.
6. Libby, P. Inflammation in atherosclerosis. Nature 2002, 420, 868-874. (Pubitemid 36019640)
7. Twiner, M.J.; Rehmann, N.; Hess, P.; Doucette, G.J. Azaspiracid Shellfish poisoning: a review on the chemistry, ecology, and toxicology with an emphasis on human health impacts. Mar. Drugs 2008, 6, 39-72.
8. Coussens, L.M. Werb, Z. Inflammation and cancer. Nature 2002, 420, 860-867.
9. Kijjoa, A.; Wattanadilok, R.; Herz, W.; Campos, N.; Nascimento, M.S.; Pinto, M. Anticancer activity evaluation of kuanoniamines A and C isolated from the marine sponge Oceanapia sagittaria, collected from the gulf of Thailand. Mar. Drugs 2007, 5, 6-22. (Pubitemid 46998586)
10. Murphy, G.; Nagase, H. Progress in matrix metalloproteinase research. Mol. Asp. Med. 2008, 29, 290-308.
11. Folgueras, A.R.; Pendas, A.M.; Sanchez, L.M.; Lopez-Otin, C. Matrix metalloproteinases in cancer: from new functions to improved inhibition strategies. Int. J. Dev. Biol. 2004, 48, 411-424.
12. Lukacova, V.; Zhang, Y.; Mackov, M.; Baricic, P.; Raha, S.; Calvo, J.A.; Balaz, S. Similarity of binding sites of human matrix metalloproteinases. J. Biol. Chem. 2004, 279, 14194-14200.
13. Maskos, K. Crystal structures of MMPs in complex with physiological and pharmacological inhibitors. Biochimie. 2005, 87, 249-263. (Pubitemid 40387604)
14. Baker, A.H.; Edwards, D.R.; Murphy, G.; Metalloproteinase inhibitors: biological actions and therapeutic opportunities. J. Cell. Sci. 2002, 115, 3719-3727.
15. Pavlaki, M.; Zucker, S. Matrix metalloproteinase inhibitors (MMPIs): the beginning of phase I or the termination of phase III clinical trials. Cancer Met. Rev. 2003, 22, 177-203.
16. Coussens, L.M.; Fingleton, B.; Matrisian, L.M. Matrix metalloproteinase inhibitors and cancer: trials and tribulations. Science 2002, 295, 2387-2392. (Pubitemid 34270240)
17. Overall, C.M.; Kleifeld, O. Tumour microenvironment - opinion: validating matrix metalloproteinases as drug targets and anti-targets for cancer therapy. Nat. Rev. Cancer 2006, 6, 227-239.
18. Overall, C.M.; Blobel, C.P. In search of partners: linking extracellular proteases to substrates, Nat. Rev. Mol. Cell. Biol. 2007, 8, 245-257.
19. Wasserman, Z.R. Making a new turn in matrix metalloprotease inhibition. Chem. Biol. 2005, 12, 143-148.
20. Engel, C.K.; Pirard, B.; Schimanski, S.; Kirsch, R.; Habermann, J.; Klingler, O.; Schlotte, V.; Weithmann, K.U.; Wendt, K.U. Structural Basis for the Highly Selective Inhibition of MMP-13. Chem. Biol. 2005, 12, 181-189.
21. Dublanchet, A.C.; Ducrot, P.; Andrianjara, C.; O'Gara, M.; Morales, R.; Compere, D.; Denis, A.; Blais, S.; Cluzeau, P.; Courte, K.; Hamon, J.; Moreau, F.; Prunet, M.L.; Tertre, A. Structure-based design and synthesis of novel non-zinc chelating MMP-12 inhibitors. Bioorg. Med. Chem. Lett. 2005, 15, 3787-3790.
22. Seo, U.K.; Lee, Y.J.; Kim, J.K.; Cha, B.Y.; Kim, D.W.; Nam, K.S.; Kim, C.H. Large-scale and effective screening of Korean medicinal plants for inhibitory activity on matrix metalloproteinase-9. J. Ethnopharmacol. 2005, 97, 101-106. (Pubitemid 40094535)
23. Ha, K.T.; Lee, T.K.; Kwak, K.H.; Kim, J.K.; Kim, D.I.; Choi, D.Y.; Kim, C.H. Inhibitory effect of Cho-Deung-San on human aortic smooth muscle cell migration induced by TNF-α through inhibition of matrix metalloproteinase-2 and -9 activity. Vasc. Pharmacol. 2004, 41, 83-90.
24. Ha, K.T.; Kim, J.K.; Kang, S.K.; Kim, D.W.; Lee, Y.C.; Kim, H.M.; Kim, C.H. Inhibitory effect of Sihoga-Yonggol-Moryo-Tang on matrix metalloproteinase-2 and -9 activities and invasiveness potential of hepatocellular carcinoma. Pharmacol. Res. 2004, 50, 279-285.
25. Kim, M.M.; Kim, S.K. Chitooligosaccharides inhibit activation and expression of matrix metalloproteinase-2 in human dermal fibroblasts. FEBS Lett. 2006, 580, 2661-2666.
26. Van Ta, Q.; Kim, M.M.; Kim, S.K. Inhibitory effect of chitooligosaccharides on matrix metalloproteinase-9 in human fibrosarcoma cells (HT1080). Mar. Biotechnol. 2006, 8, 593-599. (Pubitemid 46106885)
27. Rajapakse, N.; Kim, M.M.; Mendis, E.; Huang, R.H.; Kim, S.K. Carboxylated chitooligosaccharides (CCOS) inhibit MMP-9 expression in human fibrosarcoma cells via down-regulation of AP-1. Biochim. Biophys. Acta. 2006, 1760, 1780-1788.
28. Brito, A.S.; Arimateia, D.S.; Souza, L.R.; Lima, M.A.; Santos, V.O.; Medeiros, V.P.; Ferreira, P.A.; Silva, R.A.; Ferreira, C.V.; Justo, G.Z.; Leite, E.L.; Andrade, G.P.; Oliveira, F.W.; Nader, H.B.; Chavante, S.F. Anti-inflammatory properties of a heparin-like glycosaminoglycan with reduced anti-coagulant activity isolated from a marine shrimp. Bioorg. Med. Chem. 2008, 16, 9588-9595.
29. Rajapakse, N.; Mendis, E.; Kim, M.M.; Kim, S.K. Sulfated glucosamine inhibits MMP-2 and MMP-9 expressions in human fibrosarcoma cells. Bioorg. Med. Chem. 2007, 15, 4891-4896.
30. Chen, H.M.; Yan, X.J.; Lin, J.; Wang, F.; Xu, W.F. Depolymerized products of λ-carrageenan as a potent angiogenesis inhibitor. J. Agric. Food Chem. 2007, 55, 6910-6917.
31. Wang, S.B.; Cheng, Y.N.; Wang, F.S.; Sun, L.R.; Liu, C.H.; Chen, G.J.; Li, Y.H.; Ward, S.G.; Qu, X.J. Inhibition activity of sulfated polysaccharide of Sepiella maindroni ink on matrix metalloproteinase (MMP)-2. Biomed. Pharmacother. 2008, 62, 297-302.
32. Ye, J.; Li, Y.P.; Teruya, K.; Katakura, Y.; Ichikawa, A.; Eto, H.; Hosoi, M.; Hosoi, M.; Nishimoto, S.; Shirahata1, S. Enzyme-digested fucoidan extracts derived from seaweed Mozuku of Cladosiphon novae-caledoniae kylin inhibit invasion and angiogenesis of tumor cells. Cytotechnology 2005, 47, 117-126.
33. Kong, C.K.; Kim, Y.A.; Kim, M.M.; Park, J.S.; Kim, J.A.; Kim, S.K.; Lee, B.J.; Nam, T.J.; Seo, Y.W. Flavonoid glycosides isolated from Salicornia herbacea inhibit matrix metalloproteinase in HT1080 cells. Toxicol. Vitro 2008, 22, 1742-1748.
34. Kim, M.M.; Van Ta, Q.; Mendis, E.; Rajapakse, N.; Jung, W.K.; Byun, H.G.; Jeon, Y.J.; Kim, S.K. Phlorotannins in Ecklonia cava extract inhibit matrix metalloproteinase activity. Life Sci. 2006, 79, 1436-1443. (Pubitemid 44246994)
35. Inhee, M.J.; Kim, H.; Fan, W.Z.; Tezuka, Y.; Kadota, S.; Hishijo, H.; Jung, M.W. Neuroprotective effects of constituents of the oriental crude drugs, Rhodiola sacra, R. sachalinensis and Tokaku-joki-to, against Beta-amyloid toxicity, oxidative stress and apoptosis. Biol. Pharm. Bull. 2002, 25, 1101-1104.
36. Yoshikawa, M.; Shimada, H.; Shimoda, H.; Murakami, N.; Yamahara, J.; Matsuda, H. Bioactive constituents of Chinese natural medicines. II. Rhodiolae radix. (1). Chemical structures and antiallergic activity of rhodiocyanosides A and B from the underground part of Rhodiola quadrifida (Pall.) Fisch. et Mey. (Crassulaceae). Chem. Pharm. Bull. 1996, 44, 2086-2091.
37. Jung, W.K.; Lee, D.Y.; Kim, J.H.; Choi, I.; Park, S.G.; Seo, S.K.; Lee, S.W.; Lee, C.M.; Park, Y.M.; Jeon, Y.J.; Lee, C.H.; Jeon, B.T.; Qian, Z.J.; Kim, S.K.; Choi, I.W.; Anti-inflammatory activity of caffeic acid phenethyl ester (CAPE) extracted from Rhodiola sacra against lipopolysaccharide-induced inflammatory responses in mice. Process Biochem. 2008, 43, 783-787.
38. Joe, M.J.; Kim, S.N.; Choi, H.Y.; Shin, W.S.; Park, G.M.; Kang, D.W.; Kim, Y.K. the inhibitory effects of eckol and dieckol from Ecklonia stoloniferaon the expression of matrix metalloproteinase-1 in human dermal fibroblasts. Biol. Pharm. Bull. 2006, 29, 1735-1739.
39. Ryu, B.M.; Qian, Z.J.; Kim, M.M.; Nam, K.W.; Kim ,S.K. Anti-photoaging activity and inhibition of matrix metalloproteinase (MMP) by marine red alga, Corallina pilulifera methanol extract. Radiat. Phys. Chem. 2009, 78, 98-105.
40. Kim, S.K.; Lee, D.Y.; Jung, W.K.; Kim, J.H.; Choi, I.; Park, S.G.; Seo, S.K.; Lee, S.W.; Lee, C.M.; Yea, S.S.; Choi, Y.H.; Choi, I.W. Effects of Ecklonia cava ethanolic extracts on airway hyperresponsiveness and inflammation in a murine asthma model: Role of suppressor of cytokine signaling. Biomed. Pharmacother. 2008, 62, 289-296.
41. Ryu, B.M.; Li, Y.; Qian, Z.J.; Kim, M.M.; Kim ,S.K. Differentiation of human osteosarcoma cells by isolated phlorotannins is subtly linked to COX-2, iNOS, MMPs, and MAPK signaling: Implication for chronic articular disease. Chem.-Biol. Interact. 2009, 179, 192-201.
42. Berton, A.; Rigot, V.; Huet, E.; Decarme, M.; Eeckhout, Y.; Patthy, L.; Godeau, G.; Hornebeck, W.; Bellon, G.; Emonard, H. Involvement of fibronectin type II repeats in the efficient inhibition of gelatinases A and B by long-chain unsaturated fatty acids. J. Biol. Chem. 2001, 276, 20458-20465.
43. Sang, Q.X.; Jin, Y.H.; Newcomer, R.G.; Monroe, S.C.; Fang, X.X.; Hurst, D.R.; Lee, S.K.; Cao, Q.; Schwartz, M.A. Matrix metalloproteinase inhibitors as prospective agents for the prevention and treatment of cardiovascular and neoplastic diseases. Curr. Top. Med. Chem. 2006, 6, 289-316.
44. Ashe, B.M.; Zimmerman, M. Specific inhibition of human granulocyte elastase by cis-unsaturated fatty acids and activation by the corresponding alcohols. Biochem. Biophys. Res. Commun. 1977, 75, 194-199.
45. Tyagi, S.C.; Simon, S.R. Parinaric acids as probes of binding domains in neutrophil elastase. J. Biol. Chem. 1991, 266, 15185-15191.
46. Higazi, A.A.; Aziza, R.; Samara, A.A.; Mayer, M. Regulation of fibrinolysis by non-esterified fatty acids. Biochem. J. 1994, 300, 251-255. (Pubitemid 24151043)
47. Higazi, A.A.; Finci-Yeheskel, Z.; Samara, A.A.; Aziza, R.; Mayer, M. Stimulation of plasmin activity by oleic acid. Biochem. J. 1992, 282, 863-866.
48. Judé, S.; Roger, S.; Martel, E.; Besson, P.; Richard, S.; Bougnoux, P.; Champeroux, P.; Le Guennec, J.Y. Dietary long-chain omega-3 fatty acids of marine origin: a comparison of their protective effects on coronary heart disease and breast cancers. Prog. Biophys. Mol. Biol. 2006, 90, 299-325.
49. Suzuki, I.; Iigo, M.; Ishikawa, C.; Kuhara, T.; Asamoto, M.; Kunimoto, T.; Moore, M.A.; Yasawa, K.; Araki, E.; Tsuda, H. Inhibitory effects of oleic and docosahexaenoic acids on lung metastasis by colon-carcinoma-26 cells are associated with reduced matrix metalloproteinase-2 and -9 activities. Int. J. Cancer. 1997, 73, 607-612.
50. Harris, M.A.; Hansen, R.A.; Vidsuhiphan, P.; Koslo, J.L.; Thomas, J.B.; Watkins, B.A.; Allen, K.G. Effects of conjugated linoleic acids and docosahexaenoic acid on rat liver and preorductive tissue fatty acids, prostaglandins and matrix metalloproteinase production. Prostaglandins Leukot. Essent. Fatty Acids 2001, 65, 23-29.
51. Dai, J.R.; Hallock, Y.F.; Cardellina, J.H.; Gray, G.N.; Boyd, M.R. Triangulynes A-H and trangulynic acid, new cytotxic polyacetylenes from the marine sponge Pellina triangulata. J. Nat. Prod. 1996, 59, 860-865.
52. Li, H.Y.; Matsunaga, S.; Fusetani, N. Corticatic acids A-C, antifungal acetylenic acids from the marine sponge, Petrosia corticata. J. Nat. Prod. 1994, 57, 1464-1467.
53. Tsukamoto, S.; Kato, H.; Hirota, H.; Fusetani, N. Mauritiamine, a new antifouling oroidin dimer from the marine sponge Agelas mauritiana. J. Nat. Prod. 1997, 60, 126-130.
54. Nishimura, S.; Matsunaga, S.; Shibazaki, M.; Suzuki, K.; Harada, N.; Naoki, H.; Fusetani, N. Corticatic acids D and E, polyacetylenic geranylgeranyltransferase type I inhibitors, from the marine sponge Petrosia corticata. J. Nat. Prod. 2002, 65, 1353-1356.
55. Fujita, M.; Nakao, Y.; Matsunaga, S.; Nishikawa, T.; Fusetani, N. Sodium 1-(12-Hydroxy)octadecanyl sulfate, an MMP2 inhibitor, isolated from a tunicate of the family polyclinidae. Nat. Prod. 2002, 65, 1936-1938.
56. Fujita, M.; Nakao, Y.; Matsunaga, S.; van Soest, R.W.; Itoh, Y.; Seiki, M.; Fusetani, N. Callysponginol sulfate A, an MT1-MMP inhibitor isolated from the marine sponge Callyspongia truncata. J. Nat. Prod. 2003, 66, 569-571.
57. Cho, J.; Kim, Y. Sharks: a potential source of antiangiogenic factors and tumor treatments. Mar. Biotechnol. 2002, 4, 521-525.
58. Dupont, E., Lachance, Y., Lessard, Y., Auger, S. Low molecular weight components of shark cartilage, processes for their preparation and therapeutic uses thereof. US20010001041A1 (2001). Recent Patents on Anti-Cancer Drug Discovery 2006, 1, 135-140.
59. Gingras, D.; Renaud, A.; Mousseau, N.; Beaulieu, E.; Kachra, Z.; Beliveau, R. Matrix proteinase inhibition by AE-941, a multifunctional antiangiogenic compound. Anticancer Res. 2001, 21, 145-155. (Pubitemid 32267636)
60. Boivin, D.; Gendron, S.; Beaulieu, E.; Gingras, D.; Bèliveau, R. The antiangiogenic agent Neovastat (AE-941) induces endothelial cell apoptosis. Mol. Cancer Ther. 2002, 1, 795-802.
61. Mannello, F. Natural bio-drugs as matrix metalloproteinase inhibitors: new perspectives on the horizon?. Recent Patents Anti-Canc. Drug Discov. 2006, 1, 91-103.
62. Fujita, M.; Nakao, Y.; Matsunaga, S.; Seiki, M.; Itoh, Y.; Yamashita, J.; Van Soest, R.W.; Fusetani, N. Ageladine A: an antiangiogenic matrixmetalloproteinase inhibitor from the marine sponge Agelas nakamurai. J. Am. Chem. Soc. 2003, 125, 15700-15701.
63. Lødemel, J.B.; Egge-Jacobsen, W.; Olsen, R.L. Detection of TIMP-2-like protein in Atlantic cod (Gadus morhua) muscle using two-dimensional real-time reverse zymography. Comp. Biochem. Physiol. 2004, 139, 253-259.
64. Rodríguez-Nieto, S.; González-Iriarte, M.; Carmona, R.; Muñoz-Chápuli, R.; Medina, M.A.; Quesada, A.R. Antiangiogenic activity of aeroplysinin-1, a brominated compound isolated from a marine sponge. Faseb J. 2002, 16, 261-263.
65. Fahmy, H.; Zjawiony, J.K.; Konoshima, T.; Tokuda, H.; Khan, S.; Khalifa, S. Potent skin cancer chemopreventing activity of some novel semi-synthetic cembranoids from marine sources. mar. drugs 2006, 4, 28-36.
66. Cuniasse, P.; Devel, L.; Makaritis, A.; Beau, F.; Georgiadis, D.; Matziari, M.; Yiotakis, A.; Dive, V. Future challenges facing the development of specific active-site-directed synthetic inhibitors of MMPs. Biochimie. 2005, 87, 393-402. (Pubitemid 40387619)
67. Overall, C.M.; Kleifeld, O. Towards third generation matrix metalloproteinase inhibitors for cancer therapy. Br. J. Cancer 2006, 94, 941-946.
68. Bao, B.Q.; Zhang, P.; Lee, Y.M.; Hong, J.K.; Lee, C.O.; Jung, J.H. Monoindole alkaloids from a marine sponge Spongosorites sp. Mar. Drugs 2007, 5, 31-39. (Pubitemid 46998588)