메뉴 건너뛰기




Volumn 82, Issue 4, 2012, Pages 614-622

Anacardic acid inhibits the catalytic activity of matrix metalloproteinase-2 and matrix metalloproteinase-9

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLSALICYLIC ACID; ANACARDIC ACID; CARBOXYLIC ACID; CARDANOLIDE; GELATINASE A; GELATINASE B; GLUTAMIC ACID; SALICYLIC ACID; ZINC ION;

EID: 84866853936     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.112.079020     Document Type: Article
Times cited : (51)

References (56)
  • 1
    • 3042748128 scopus 로고    scopus 로고
    • The role of COX-2 inhibition in breast cancer treatment and prevention
    • DOI 10.1016/j.seminoncol.2004.03.042, PII S0093775404001915
    • Arun B and Goss P (2004) The role of COX-2 inhibition in breast cancer treatment and prevention. Semin Oncol 31:22-29. (Pubitemid 38879411)
    • (2004) Seminars in Oncology , vol.31 , Issue.SUPPL. 7 , pp. 22-29
    • Arun, B.1    Goss, P.2
  • 4
    • 0035827538 scopus 로고    scopus 로고
    • Involvement of fibronectin type II repeats in the efficient inhibition of gelatinases A and B by long-chain unsaturated fatty acids
    • Berton A, Rigot V, Huet E, Decarme M, Eeckhout Y, Patthy L, Godeau G, Hornebeck W, Bellon G, and Emonard H (2001) Involvement of fibronectin type II repeats in the efficient inhibition of gelatinases A and B by long-chain unsaturated fatty acids. J Biol Chem 276:20458-20465.
    • (2001) J Biol Chem , vol.276 , pp. 20458-20465
    • Berton, A.1    Rigot, V.2    Huet, E.3    Decarme, M.4    Eeckhout, Y.5    Patthy, L.6    Godeau, G.7    Hornebeck, W.8    Bellon, G.9    Emonard, H.10
  • 5
    • 15844420283 scopus 로고    scopus 로고
    • Localization of matrix metalloproteinase MMP-2 to the surface of invasive cells by interaction with integrin αvβ3
    • DOI 10.1016/S0092-8674(00)81235-0
    • Brooks PC, Strömblad S, Sanders LC, von Schalscha TL, Aimes RT, Stetler-Stevenson WG, Quigley JP, and Cheresh DA (1996) Localization of matrix metalloproteinase MMP-2 to the surface of invasive cells by interaction with integrin αvβ3. Cell 85:683-693. (Pubitemid 26181048)
    • (1996) Cell , vol.85 , Issue.5 , pp. 683-693
    • Brooks, P.C.1    Stromblad, S.2    Sanders, L.C.3    Von Schalscha, T.L.4    Aimes, R.T.5    Stetler-Stevenson, W.G.6    Quigley, J.P.7    Cheresh, D.A.8
  • 7
    • 34748861551 scopus 로고    scopus 로고
    • Characterization of novel inhibitors of histone acetyltransferases
    • DOI 10.1158/1535-7163.MCT-07-0159
    • Eliseeva ED, Valkov V, Jung M, and Jung MO (2007) Characterization of novel inhibitors of histone acetyltransferases. Mol Cancer Ther 6:2391-2398. (Pubitemid 47480404)
    • (2007) Molecular Cancer Therapeutics , vol.6 , Issue.9 , pp. 2391-2398
    • Eliseeva, E.D.1    Valkov, V.2    Jung, M.3    Jung, M.O.4
  • 11
    • 34447627700 scopus 로고    scopus 로고
    • Molecular design of anti-MRSA agents based on the anacardic acid scaffold
    • DOI 10.1016/j.bmc.2007.06.022, PII S0968089607005457
    • Green IR, Tocoli FE, Lee SH, Nihei K, and Kubo I (2007) Molecular design of anti-MRSA agents based on the anacardic acid scaffold. Bioorg Med Chem 15:6236-6241. (Pubitemid 47088953)
    • (2007) Bioorganic and Medicinal Chemistry , vol.15 , Issue.18 , pp. 6236-6241
    • Green, I.R.1    Tocoli, F.E.2    Lee, S.H.3    Nihei, K.-i.4    Kubo, I.5
  • 12
    • 44349099730 scopus 로고    scopus 로고
    • Design and evaluation of anacardic acid derivatives as anticavity agents
    • DOI 10.1016/j.ejmech.2007.08.012, PII S0223523407003340
    • Green IR, Tocoli FE, Lee SH, Nihei K, and Kubo I (2008) Design and evaluation of anacardic acid derivatives as anticavity agents. Eur J Med Chem 43:1315-1320. (Pubitemid 351734556)
    • (2008) European Journal of Medicinal Chemistry , vol.43 , Issue.6 , pp. 1315-1320
    • Green, I.R.1    Tocoli, F.E.2    Lee, S.H.3    Nihei, K.-i.4    Kubo, I.5
  • 13
    • 20744457367 scopus 로고    scopus 로고
    • Lipoxygenase inhibitory activity of anacardic acids
    • DOI 10.1021/jf048184e
    • Ha TJ and Kubo I (2005) Lipoxygenase inhibitory activity of anacardic acids. J Agric Food Chem 53:4350-4354. (Pubitemid 40855456)
    • (2005) Journal of Agricultural and Food Chemistry , vol.53 , Issue.11 , pp. 4350-4354
    • Ha, T.J.1    Kubo, I.2
  • 14
    • 0035571790 scopus 로고    scopus 로고
    • A comparative docking study and the design of potentially selective MMP inhibitors
    • DOI 10.1023/A:1014356529909
    • Hanessian S, Moitessier N, and Therrien E (2001) A comparative docking study and the design of potentially selective MMP inhibitors. J Comput Aided Mol Des 15:873-881. (Pubitemid 34218291)
    • (2001) Journal of Computer-Aided Molecular Design , vol.15 , Issue.10 , pp. 873-881
    • Hanessian, S.1    Moitessier, N.2    Therrien, E.3
  • 16
    • 0001506081 scopus 로고
    • Antibacterial agents from the cashew Anacardium occidentale (Anacardiaceae) nut shell oil
    • Himejima M and Kubo IJ (1991) Antibacterial agents from the cashew Anacardium occidentale (Anacardiaceae) nut shell oil. Agric Food Chem 39:418-421.
    • (1991) Agric Food Chem , vol.39 , pp. 418-421
    • Himejima, M.1    Kubo, I.J.2
  • 17
    • 63449131596 scopus 로고    scopus 로고
    • Matrix metalloproteinase-2 involvement in breast cancer progression: A mini-review
    • Jezierska A and Motyl T (2009) Matrix metalloproteinase-2 involvement in breast cancer progression: a mini-review. Med Sci Monit 15:RA32-RA40.
    • (2009) Med Sci Monit , vol.15
    • Jezierska, A.1    Motyl, T.2
  • 19
    • 62849110321 scopus 로고    scopus 로고
    • The role of p300 histone acetyltransferase in UV-induced histone modifications and MMP-1 gene transcription
    • Kim MK, Shin JM, Eun HC, and Chung JH (2009) The role of p300 histone acetyltransferase in UV-induced histone modifications and MMP-1 gene transcription. PLoS One 4:e4864.
    • (2009) PLoS One , vol.4
    • Kim, M.K.1    Shin, J.M.2    Eun, H.C.3    Chung, J.H.4
  • 21
    • 0026505650 scopus 로고
    • A novel coumarin-labelled peptide for sensitive continuous assays of the matrix metalloproteinases
    • Knight CG, Willenbrock F, and Murphy G (1992) A novel coumarin-labelled peptide for sensitive continuous assays of the matrix metalloproteinases. FEBS Lett 296:263-266.
    • (1992) FEBS Lett , vol.296 , pp. 263-266
    • Knight, C.G.1    Willenbrock, F.2    Murphy, G.3
  • 22
    • 0028287786 scopus 로고
    • Tyrosinase inhibitors from Anacardium occidentale fruits
    • Kubo I, Kinst-Hori I, and Yokokawa Y (1994a) Tyrosinase inhibitors from Anacardium occidentale fruits. J Nat Prod 57:545-551. (Pubitemid 24152917)
    • (1994) Journal of Natural Products , vol.57 , Issue.4 , pp. 545-551
    • Kubo, I.1    Kinst-Hori, I.2    Yokokawa, Y.3
  • 23
  • 25
    • 0348110247 scopus 로고    scopus 로고
    • Antibacterial action of anacardic acids against methicillin resistant Staphylococcus aureus (MRSA)
    • Kubo I, Nihei K, and Tsujimoto K (2003) Antibacterial action of anacardic acids against methicillin resistant Staphylococcus aureus (MRSA). J Agric Food Chem 51:7624-7628.
    • (2003) J Agric Food Chem , vol.51 , pp. 7624-7628
    • Kubo, I.1    Nihei, K.2    Tsujimoto, K.3
  • 26
  • 27
    • 0033403626 scopus 로고    scopus 로고
    • Cyclooxygenase-deficient mice. A summary of their characteristics and susceptibilities to inflammation and carcinogenesis
    • Langenbach R, Loftin CD, Lee C, and Tiano H (1999) Cyclooxygenase- deficient mice. A summary of their characteristics and susceptibilities to inflammation and carcinogenesis. Ann NY Acad Sci 889:52-61. (Pubitemid 30040425)
    • (1999) Annals of the New York Academy of Sciences , vol.889 , pp. 52-61
    • Langenbach, R.1    Loftin, C.D.2    Christopher, L.3    Tiano, H.4
  • 28
    • 70450181696 scopus 로고    scopus 로고
    • Selective matrix metalloproteinase inhibitors for cancer
    • Lia NG, Shib ZH, Tang YP, and Duan JA (2009) Selective matrix metalloproteinase inhibitors for cancer. Curr Med Chem 16:3805-3827.
    • (2009) Curr Med Chem , vol.16 , pp. 3805-3827
    • Lia, N.G.1    Shib, Z.H.2    Tang, Y.P.3    Duan, J.A.4
  • 29
    • 0019195010 scopus 로고
    • Metastatic potential correlates with enzymatic degradation of basement membrane collagen
    • Liotta LA, Tryggvason K, Garbisa S, Hart I, Foltz CM, and Shafie S (1980) Metastatic potential correlates with enzymatic degradation of basement membrane collagen. Nature 284:67-68. (Pubitemid 10098769)
    • (1980) Nature , vol.284 , Issue.5751 , pp. 67-68
    • Liotta, L.A.1    Tryggvason, K.2    Garbisa, S.3
  • 31
    • 34047252538 scopus 로고    scopus 로고
    • Natural bio-drugs as matrix metalloproteinase inhibitors: New perspectives on the horizon?
    • Mannello F (2006) Natural bio-drugs as matrix metalloproteinase inhibitors: new perspectives on the horizon? Recent Pat Anticancer Drug Discov 1:91-103.
    • (2006) Recent Pat Anticancer Drug Discov , vol.1 , pp. 91-103
    • Mannello, F.1
  • 33
    • 1842421086 scopus 로고    scopus 로고
    • Characterization of xanthine oxidase inhibition by anacardic acids
    • DOI 10.1016/j.bbadis.2003.12.010, PII S0925443903002059
    • Masuoka N and Kubo I (2004) Characterization of xanthine oxidase inhibition by anacardic acids. Biochim Biophys Acta 1688:245-249. (Pubitemid 38438528)
    • (2004) Biochimica et Biophysica Acta - Molecular Basis of Disease , vol.1688 , Issue.3 , pp. 245-249
    • Masuoka, N.1    Kubo, I.2
  • 34
    • 0026001376 scopus 로고
    • Molluscacide activity of a mixture of 6-n-alkyl salicylic acids (anacardic acid) and 2 of its complexes with copper (II) and lead (II)
    • Mendes NM, de Oliveira AB, Guimarães JE, Pereira JP, and Katz N (1990) Molluscacide activity of a mixture of 6-n-alkyl salicylic acids (anacardic acid) and 2 of its complexes with copper (II) and lead (II). Rev Soc Bras Med Trop 23:217-224.
    • (1990) Rev Soc Bras Med Trop , vol.23 , pp. 217-224
    • Mendes, N.M.1    De Oliveira, A.B.2    Guimarães, J.E.3    Pereira, J.P.4    Katz, N.5
  • 38
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays
    • Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55-63.
    • (1983) J Immunol Methods , vol.65 , pp. 55-63
    • Mosmann, T.1
  • 39
    • 0001636745 scopus 로고
    • Structure-antibacterial activity relationships of anacardic acids
    • Muroi H and Kubo I (1993) Structure-antibacterial activity relationships of anacardic acids. J Agric Food Chem 41:1780-1783.
    • (1993) J Agric Food Chem , vol.41 , pp. 1780-1783
    • Muroi, H.1    Kubo, I.2
  • 40
    • 0029930244 scopus 로고    scopus 로고
    • Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant Staphylococcus aureus
    • Muroi H and Kubo I (1996) Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin- resistant Staphylococcus aureus. J Appl Bacteriol 80:387-394.
    • (1996) J Appl Bacteriol , vol.80 , pp. 387-394
    • Muroi, H.1    Kubo, I.2
  • 42
    • 0034854976 scopus 로고    scopus 로고
    • Novel method for isolation of major phenolic constituents from cashew (Anacardium occidentale L.) Nut shell liquid
    • DOI 10.1021/jf001222j
    • Paramashivappa R, Kumar PP, Vithayathil PJ, and Rao AS (2001) Novel method for isolation of major phenolic constituents from cashew (Anacardium occidentale L.) nut shell liquid. J Agric Food Chem 49:2548-2551. (Pubitemid 32843289)
    • (2001) Journal of Agricultural and Food Chemistry , vol.49 , Issue.5 , pp. 2548-2551
    • Paramashivappa, R.1    Phani, K.P.2    Vithayathil, P.J.3    Srinivasa, R.A.4
  • 44
    • 67651083303 scopus 로고    scopus 로고
    • p38α MAP kinase C-terminal domain binding pocket characterized by crystallographic and computational analyses
    • Perry JJ, Harris RM, Moiani D, Olson AJ, and Tainer JA (2009) p38α MAP kinase C-terminal domain binding pocket characterized by crystallographic and computational analyses. J Mol Biol 391:1-11.
    • (2009) J Mol Biol , vol.391 , pp. 1-11
    • Perry, J.J.1    Harris, R.M.2    Moiani, D.3    Olson, A.J.4    Tainer, J.A.5
  • 45
    • 55549144382 scopus 로고    scopus 로고
    • Isolation of anacardic acid from natural cashew nut shell liquid (CNSL) using supercritical carbon dioxide
    • Philip JY, Da Cruz Francisco J, Dey ES, Buchweishaija J, Mkayula LL, and Ye L (2008) Isolation of anacardic acid from natural cashew nut shell liquid (CNSL) using supercritical carbon dioxide. J Agric Food Chem 56:9350-9354.
    • (2008) J Agric Food Chem , vol.56 , pp. 9350-9354
    • Philip, J.Y.1    Da Cruz Francisco, J.2    Dey, E.S.3    Buchweishaija, J.4    Mkayula, L.L.5    Ye, L.6
  • 46
    • 0036850364 scopus 로고    scopus 로고
    • Gelatin zymography and substrate cleavage assays of matrix metalloproteinase-2 in breast carcinoma cells overexpressing membrane type-1 matrix metalloproteinase
    • Ratnikov BI, Deryugina EI, and Strongin AY (2002) Gelatin zymography and substrate cleavage assays of matrix metalloproteinase-2 in breast carcinoma cells overexpressing membrane type-1 matrix metalloproteinase. Lab Invest 82:1583-1590. (Pubitemid 35332917)
    • (2002) Laboratory Investigation , vol.82 , Issue.11 , pp. 1583-1590
    • Ratnikov, B.I.1    Deryugina, E.I.2    Strongin, A.Y.3
  • 49
    • 0038575443 scopus 로고    scopus 로고
    • Extracellular matrix remodelling: The role of matrix metalloproteinases
    • Stamenkovic I (2003) Extracellular matrix remodelling: the role of matrix metalloproteinases. J Pathol 200:448-464.
    • (2003) J Pathol , vol.200 , pp. 448-464
    • Stamenkovic, I.1
  • 50
    • 46749127067 scopus 로고    scopus 로고
    • Anacardic acid (6-nonadecyl salicylic acid), an inhibitor of histone acetyltransferase, suppresses expression of nuclear factor-κB-regulated gene products involved in cell survival, proliferation, invasion, and inflammation through inhibition of the inhibitory subunit of nuclear factor-κBα kinase, leading to potentiation of apoptosis
    • Sung B, Pandey MK, Ahn KS, Yi T, Chaturvedi MM, Liu M, and Aggarwal BB (2008) Anacardic acid (6-nonadecyl salicylic acid), an inhibitor of histone acetyltransferase, suppresses expression of nuclear factor-κB-regulated gene products involved in cell survival, proliferation, invasion, and inflammation through inhibition of the inhibitory subunit of nuclear factor-κBα kinase, leading to potentiation of apoptosis. Blood 111:4880-4891.
    • (2008) Blood , vol.111 , pp. 4880-4891
    • Sung, B.1    Pandey, M.K.2    Ahn, K.S.3    Yi, T.4    Chaturvedi, M.M.5    Liu, M.6    Aggarwal, B.B.7
  • 51
    • 33847412751 scopus 로고    scopus 로고
    • Synthesis of isonicotinoylhydrazones from anacardic acid and their in vitro activity against Mycobacterium smegmatis
    • DOI 10.1016/j.ejmech.2006.09.009, PII S0223523406003278
    • Swamy BN, Suma TK, Rao GV, and Reddy GC (2007) Synthesis of isonicotinoylhydrazones from anacardic acid and their in vitro activity against Mycobacterium smegmatis. Eur J Med Chem 42:420-424. (Pubitemid 46349365)
    • (2007) European Journal of Medicinal Chemistry , vol.42 , Issue.3 , pp. 420-424
    • Swamy, B.N.1    Suma, T.K.2    Rao, G.V.3    Reddy, G.C.4
  • 52
    • 34548670257 scopus 로고    scopus 로고
    • Crystal Structures of MMP-9 Complexes with Five Inhibitors: Contribution of the Flexible Arg424 Side-chain to Selectivity
    • DOI 10.1016/j.jmb.2007.05.068, PII S0022283607007085
    • Tochowicz A, Maskos K, Huber R, Oltenfreiter R, Dive V, Yiotakis A, Zanda M, Pourmotabbed T, Bode W, and Goettig P (2007) Crystal structures of MMP-9 complexes with five inhibitors: contribution of the flexible Arg424 side-chain to selectivity. J Mol Biol 371:989-1006. (Pubitemid 47411454)
    • (2007) Journal of Molecular Biology , vol.371 , Issue.4 , pp. 989-1006
    • Tochowicz, A.1    Maskos, K.2    Huber, R.3    Oltenfreiter, R.4    Dive, V.5    Yiotakis, A.6    Zanda, M.7    Bode, W.8    Goettig, P.9
  • 53
    • 28844482294 scopus 로고    scopus 로고
    • Characterization of alkyl phenols in cashew (Anacardium occidentale) products and assay of their antioxidant capacity
    • DOI 10.1016/j.fct.2005.06.012, PII S0278691505002243
    • Trevisan MT, Pfundstein B, Haubner R, Würtele G, Spiegelhalder B, Bartsch H, and Owen RW (2006) Characterization of alkyl phenols in cashew (Anacardium occidentale) products and assay of their antioxidant capacity. Food Chem Toxicol 44:188-197. (Pubitemid 41773813)
    • (2006) Food and Chemical Toxicology , vol.44 , Issue.2 , pp. 188-197
    • Trevisan, M.T.S.1    Pfundstein, B.2    Haubner, R.3    Wurtele, G.4    Spiegelhalder, B.5    Bartsch, H.6    Owen, R.W.7
  • 55
    • 0033848986 scopus 로고    scopus 로고
    • Matrix metalloproteinases: Effectors of development and normal physiology
    • Vu TH and Werb Z (2000) Matrix metalloproteinases: effectors of development and normal physiology. Genes Dev 14:2123-2133.
    • (2000) Genes Dev , vol.14 , pp. 2123-2133
    • Vu, T.H.1    Werb, Z.2
  • 56
    • 0024330327 scopus 로고
    • SV40-transformed human lung fibroblasts secrete a 92-kDa type IV collagenase which is identical to that secreted by normal human macrophages
    • Wilhelm SM, Collier IE, Marmer BL, Eisen AZ, Grant GA, and Goldberg GI (1989) SV40-transformed human lung fibroblasts secrete a 92-kDa type IV collagenase which is identical to that secreted by normal human macrophages. J Biol Chem 264:17213-17221. (Pubitemid 19255553)
    • (1989) Journal of Biological Chemistry , vol.264 , Issue.29 , pp. 17213-17221
    • Wilhelm, S.M.1    Collier, I.E.2    Marmer, B.L.3    Eisen, A.Z.4    Grant, G.A.5    Goldberg, G.I.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.