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Volumn 73, Issue 6, 2012, Pages 317-324

Design, synthesis, and preliminary evaluation of substituted cinnamic acid esters as selective matrix metalloproteinase inhibitors

Author keywords

activity relationship; caffeic acid; matrix metalloproteinases; structure; tumor

Indexed keywords

BENZENE; CAFFEIC ACID; CINNAMIC ACID DERIVATIVE; CYCLOHEXYL 3 (3,4 DIHYDROXYPHENYL)ACRYLATE; CYCLOHEXYL 3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLATE; CYCLOHEXYL CINNAMATE; CYCLOPENTYL 3 (3,4 DIHYDROXYPHENYL)ACRYLATE; CYCLOPENTYL CINNAMATE; GELATINASE A; GELATINASE B; HYDROXYL RADICAL; INTERSTITIAL COLLAGENASE; ISOBUTYL 3 (3,4 DIHYDROXYPHENYL)ACRYLATE; ISOBUTYL CINNAMATE; ISOPENTYL 3 (3,4 DIHYDROXYPHENYL)ACRYLATE; ISOPENTYL CINNAMATE; ISOPROPYL 3 (3,4 DIHYDROXYPHENYL)ACRYLATE; ISOPROPYL CINNAMATE; MATRIX METALLOPROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 84866388387     PISSN: 02724391     EISSN: 10982299     Source Type: Journal    
DOI: 10.1002/ddr.21015     Document Type: Article
Times cited : (11)

References (33)
  • 1
    • 0028947020 scopus 로고
    • Matrix metalloproteinase-2 is an interstitial collagenase: Inhibitor-free enzyme catalyzes the cleavage of collagen fibrils and soluble native type i collagen generating the specific 3/4- and 1/4-length fragments
    • Aimes RT, Quigley JP,. 1995. Matrix metalloproteinase-2 is an interstitial collagenase: inhibitor-free enzyme catalyzes the cleavage of collagen fibrils and soluble native type I collagen generating the specific 3/4- and 1/4-length fragments. J Biol Chem 270: 5872-5876.
    • (1995) J Biol Chem , vol.270 , pp. 5872-5876
    • Aimes, R.T.1    Quigley, J.P.2
  • 4
    • 7744221596 scopus 로고    scopus 로고
    • Novel and therapeutic effect of caffeic acid and caffeic acid phenyl ester on hepatocarcinoma cells: Complete regression of hepatoma growth and metastasis by dual mechanism
    • DOI 10.1096/fj.04-2126com
    • Chung TW, Moon SK, Chang YC, Ko JH, Lee YC, Cho G, Kim SH, Kim JG, Kim CH,. 2004. Novel and therapeutic effect of caffeic acid and caffeic acid phenyl ester on hepatocarcinoma cells: complete regression of hepatoma growth and metastasis by dual mechanism. FASEB J 18: 1670-1681. (Pubitemid 39463706)
    • (2004) FASEB Journal , vol.18 , Issue.14 , pp. 1670-1681
    • Chung, T.-W.1    Moon, S.-K.2    Chang, Y.-C.3    Ko, J.-H.4    Lee, Y.-C.5    Cho, G.6    Kim, S.-H.7    Kim, J.-G.8    Kim, C.-H.9
  • 5
    • 0028556638 scopus 로고
    • Reciprocated matrix metalloproteinase activation: A process performed by interstitial collagenase and progelatinase A
    • Crabbe T, O'Connel JP, Smith BJ, Docherty AJP,. 1994. Reciprocated matrix metalloproteinase activation: a process performed by interstitial collagenase and progelatinase A. Biochemistry 33: 14419-14425.
    • (1994) Biochemistry , vol.33 , pp. 14419-14425
    • Crabbe, T.1    O'Connel, J.P.2    Smith, B.J.3    Docherty, A.J.P.4
  • 6
    • 18244427699 scopus 로고    scopus 로고
    • Selective enhancement of collagenase-mediated cleavage of resident type II collagen in cultured osteoarthritic cartilage and arrest with a synthetic inhibitor that spares collagenase 1 (Matrix metalloproteinase 1)
    • DOI 10.1002/1529-0131(200003)43:3<673::AID-ANR25>3.0.CO;2-8
    • Dahlberg L, Billinghurst RC, Manner P, Nelson F, Webb G, Ionescu M, Reiner A, Tanzer M, Zukor D, Chen J, et al. 2000. Selective enhancement of collagenase-mediated cleavage of resident type II collagen in cultured osteoarthritic cartilage and arrest with a synthetic inhibitor that spares collagenase 1 (matrix metalloproteinase 1). Arthritis Rheum 43: 673-682. (Pubitemid 30394960)
    • (2000) Arthritis and Rheumatism , vol.43 , Issue.3 , pp. 673-682
    • Dahlberg, L.1    Billinghurst, R.C.2    Webb, G.3    Ionescu, M.4    Reiner, A.5    Poole, A.R.6    Manner, P.7    Tanzer, M.8    Nelson, F.9    Zukor, D.10    Chen, J.11    Van Wart, H.E.12
  • 8
    • 0029003620 scopus 로고
    • Remodeling MMPIs
    • Hodgson J,. 1995. Remodeling MMPIs. Biotechnology 13: 554-557.
    • (1995) Biotechnology , vol.13 , pp. 554-557
    • Hodgson, J.1
  • 10
    • 0031716672 scopus 로고    scopus 로고
    • Dupuytren's disease and frozen shoulder induced by treatment with a matrix metalloproteinase inhibitor
    • DOI 10.1302/0301-620X.80B5.8464
    • Hutchinson JW, Tierney GM, Parsons SL, Davis TRC,. 1998. Dupuytren's disease and frozen shoulder induced by treatment with a matrix metalloproteinase inhibitor. J Bone Joint Surg Br 80-B: 907-908. (Pubitemid 28457089)
    • (1998) Journal of Bone and Joint Surgery - Series B , vol.80 , Issue.5 , pp. 907-908
    • Hutchinson, J.W.1    Tierney, G.M.2    Parsons, S.L.3    Davis, T.R.C.4
  • 11
    • 11144325118 scopus 로고    scopus 로고
    • Controlled microwave heating in modern organic synthesis
    • DOI 10.1002/anie.200400655
    • Kappe CO,. 2004. Controlled microwave heating in modern organic synthesis. Angew Chem Int Ed Engl 43: 6250-6284. (Pubitemid 40036603)
    • (2004) Angewandte Chemie - International Edition , vol.43 , Issue.46 , pp. 6250-6284
    • Kappe, C.O.1
  • 12
    • 70450181696 scopus 로고    scopus 로고
    • Selective matrix metalloproteinase inhibitors for cancer
    • Li NG, Shi ZH, Tang YP, Duan JA,. 2009a. Selective matrix metalloproteinase inhibitors for cancer. Curr Med Chem 16: 3805-3827.
    • (2009) Curr Med Chem , vol.16 , pp. 3805-3827
    • Li, N.G.1    Shi, Z.H.2    Tang, Y.P.3    Duan, J.A.4
  • 13
    • 67649845980 scopus 로고    scopus 로고
    • Highly efficient esterification of ferulic acid under microwave irradiation
    • Li NG, Shi ZH, Tang YP, Li BQ, Duan JA,. 2009b. Highly efficient esterification of ferulic acid under microwave irradiation. Molecules 14: 2118-2126.
    • (2009) Molecules , vol.14 , pp. 2118-2126
    • Li, N.G.1    Shi, Z.H.2    Tang, Y.P.3    Li, B.Q.4    Duan, J.A.5
  • 14
    • 0032874630 scopus 로고    scopus 로고
    • Catalytic esterifications of carboxylic acids and alcohols by sodium bisulfate monohydrate
    • Li YQ,. 1999. Catalytic esterifications of carboxylic acids and alcohols by sodium bisulfate monohydrate. Synth Commun 29: 3901-3903.
    • (1999) Synth Commun , vol.29 , pp. 3901-3903
    • Li, Y.Q.1
  • 16
    • 0029594498 scopus 로고
    • Contributions of tumor and stromal matrix metalloproteinases to tumor progression, invasion and metastasis
    • DOI 10.1007/BF00690603
    • MacDougall JR, Matrisian LM,. 1995. Contributions of tumor and stromal matrix metalloproteinases to tumor progression, invasion and metastasis. Cancer Metastasis Rev 14: 351-362. (Pubitemid 26030973)
    • (1995) Cancer and Metastasis Reviews , vol.14 , Issue.4 , pp. 351-362
    • MacDougall, J.R.1    Matrisian, L.M.2
  • 18
    • 0034739324 scopus 로고    scopus 로고
    • Suppressive effects of novel ferulic acid derivatives on cellular responses induced by phorbol ester, and by combined lipopolysaccharide and interferon-γ
    • DOI 10.1016/S0304-3835(00)00478-X, PII S030438350000478X
    • Murakami A, Kadota M, Takahashi D, Taniguchi H, Nomura E, Hosoda A, Tsuno T, Maruta Y, Ohigashi H, Oshimizu K,. 2000. Suppressive effects of novel ferulic acid derivatives on cellular responses induced by phorbol ester, and by combined lipopolysaccharide and interferon-γ. Cancer Lett 157: 77-85. (Pubitemid 30421234)
    • (2000) Cancer Letters , vol.157 , Issue.1 , pp. 77-85
    • Murakami, A.1    Kadota, M.2    Takahashi, D.3    Taniguchi, H.4    Nomura, E.5    Hosoda, A.6    Tsuno, T.7    Maruta, Y.8    Ohigashi, H.9    Koshimizu, K.10
  • 19
    • 0036336025 scopus 로고    scopus 로고
    • Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-Metastatic murine colon 26-L5 carcinoma cell line
    • DOI 10.1016/S0968-0896(02)00138-4, PII S0968089602001384
    • Nagaoka T, Banskota AH, Tezuka Y, Saiki I, Kadota S,. 2002. Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-metastatic murine colon 26-L5 carcinoma cell line. Bioorg Med Chem 10: 3351-3359. (Pubitemid 34863215)
    • (2002) Bioorganic and Medicinal Chemistry , vol.10 , Issue.10 , pp. 3351-3359
    • Nagaoka, T.1    Banskota, A.H.2    Tezuka, Y.3    Saiki, I.4    Kadota, S.5
  • 20
    • 0033618337 scopus 로고    scopus 로고
    • Matrix metalloproteinases
    • Nagase H, Woessner JF Jr,. 1999. Matrix metalloproteinases. J Biol Chem 274: 21491-21494.
    • (1999) J Biol Chem , vol.274 , pp. 21491-21494
    • Nagase, H.1    Woessner Jr., J.F.2
  • 21
    • 4644257234 scopus 로고    scopus 로고
    • Esters, amides and substituted derivatives of cinnamic acid: Synthesis, antimicrobial activity and QSAR investigations
    • DOI 10.1016/j.ejmech.2004.06.013, PII S0223523404001539
    • Narasimhana B, Belsareb D, Pharandeb D, Mouryac V, Dhake A,. 2004. Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations. Eur J Med Chem 39: 827-834. (Pubitemid 39302632)
    • (2004) European Journal of Medicinal Chemistry , vol.39 , Issue.10 , pp. 827-834
    • Narasimhan, B.1    Belsare, D.2    Pharande, D.3    Mourya, V.4    Dhake, A.5
  • 22
    • 34447136548 scopus 로고
    • 2, a superacidic perfluorinated resinsulfonic acid catalyst
    • 2, a superacidic perfluorinated resinsulfonic acid catalyst. Synthesis 12: 929-930.
    • (1978) Synthesis , vol.12 , pp. 929-930
    • Olah, G.A.1    Keumi, T.2    Meidar, D.3
  • 23
    • 0036716282 scopus 로고    scopus 로고
    • Strategies for MMP inhibition in cancer: Innovations for the post-trial era
    • DOI 10.1038/nrc884
    • Overall CM, Lõpez-Otín C,. 2002. Strategies for MMP inhibition in cancer: innovations for the post-trial era. Nat Rev Cancer 2: 657-672. (Pubitemid 37328917)
    • (2002) Nature Reviews Cancer , vol.2 , Issue.9 , pp. 657-672
    • Overall, C.M.1    Lopez-Otin, C.2
  • 24
    • 12344329635 scopus 로고    scopus 로고
    • A new matrix metalloproteinase-9 inhibitor 3,4-dihydroxycinnamic acid (caffeic acid) from methanol extract of Euonymus alatus: Isolation and structure determination
    • Park WH, Kim SH, Kim CH,. 2005. A new matrix metalloproteinase-9 inhibitor 3,4-dihydroxycinnamic acid (caffeic acid) from methanol extract of Euonymus alatus: isolation and structure determination. Toxicology 207: 383-390.
    • (2005) Toxicology , vol.207 , pp. 383-390
    • Park, W.H.1    Kim, S.H.2    Kim, C.H.3
  • 26
    • 0033864065 scopus 로고    scopus 로고
    • Prinomastat, a hydroxamate-based matrix metalloproteinase inhibitor. A novel pharmacological approach for tissue remodelling-related diseases
    • Scatena R,. 2000. Prinomastat, a hydroxamate-based matrix metalloproteinase inhibitor. A novel pharmacological approach for tissue remodelling-related diseases. Exp Opin Invest Drugs 9: 2159-2165.
    • (2000) Exp Opin Invest Drugs , vol.9 , pp. 2159-2165
    • Scatena, R.1
  • 27
    • 33749267261 scopus 로고    scopus 로고
    • Flavonoids and cinnamic acid esters as inhibitors of fungal 17β-hydroxysteroid dehydrogenase: A synthesis, QSAR and modelling study
    • DOI 10.1016/j.bmc.2006.07.027, PII S0968089606005815
    • Sova M, Perdih A, Kotnik M, Kristan K, Lanišnik Rižner T, Solmajer T, Gobec S,. 2006. Flavonoids and cinnamic acid esters as inhibitors of fungal 17β-hydroxysteroid dehydrogenase: a synthesis, QSAR and modelling study. Bioorg Med Chem 14: 7404-7418. (Pubitemid 44486808)
    • (2006) Bioorganic and Medicinal Chemistry , vol.14 , Issue.22 , pp. 7404-7418
    • Sova, M.1    Perdih, A.2    Kotnik, M.3    Kristan, K.4    Rizner, T.L.5    Solmajer, T.6    Gobec, S.7
  • 28
    • 0033134622 scopus 로고    scopus 로고
    • Matrix metalloproteinases in angiogenesis: A moving target for therapeutic intervention
    • Stetler-Stevenson WG,. 1999. Matrix metalloproteinases in angiogenesis: a moving target for therapeutic intervention. J Clin Invest 103: 1237-1241. (Pubitemid 29218293)
    • (1999) Journal of Clinical Investigation , vol.103 , Issue.9 , pp. 1237-1241
    • Stetler-Stevenson, W.G.1
  • 30
    • 1242352467 scopus 로고    scopus 로고
    • 2-Catalyzed Oxidative Coupling Reaction of Benzenes with Olefins in the Presence of Molybdovanadophosphoric Acid under Atmospheric Dioxygen and Air
    • DOI 10.1021/jo035568f
    • 2-catalyzed oxidative coupling reaction of benzenes with olefins in the presence of molybdovanadophosphoric acid under atmospheric dioxygen and air. J Org Chem 69: 1221-1226. (Pubitemid 38233404)
    • (2004) Journal of Organic Chemistry , vol.69 , Issue.4 , pp. 1221-1226
    • Tani, M.1    Sakaguchi, S.2    Ishii, Y.3
  • 31
    • 49149127810 scopus 로고    scopus 로고
    • Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages
    • Uwai K, Osanai Y, Imaizumi T, Kanno S, Takeshita M, Ishikaw M,. 2008. Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages. Bioorg Med Chem 16: 7795-7803.
    • (2008) Bioorg Med Chem , vol.16 , pp. 7795-7803
    • Uwai, K.1    Osanai, Y.2    Imaizumi, T.3    Kanno, S.4    Takeshita, M.5    Ishikaw, M.6
  • 32
    • 33846906016 scopus 로고    scopus 로고
    • Matrix metalloproteinases (MMPs): Chemical-biological functions and (Q)SARs
    • DOI 10.1016/j.bmc.2007.01.011, PII S0968089607000260
    • Verma RP, Hansch C,. 2007. Matrix metalloproteinases (MMPs): chemical-biological functions and (Q)SARs. Bioorg Med Chem 15: 2223-2268. (Pubitemid 46240907)
    • (2007) Bioorganic and Medicinal Chemistry , vol.15 , Issue.6 , pp. 2223-2268
    • Verma, R.P.1    Hansch, C.2
  • 33
    • 0033043890 scopus 로고    scopus 로고
    • 2O in synthesis: A convenient and efficient catalyst for the esterification of aromatic carboxylic acids with alcohols
    • 2O in synthesis: a convenient and efficient catalyst for the esterification of aromatic carboxylic acids with alcohols. Synth Commun 29: 607-611.
    • (1999) Synth Commun , vol.29 , pp. 607-611
    • Zhang, G.S.1


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