메뉴 건너뛰기




Volumn 79, Issue 1, 2012, Pages 112-120

Comparison of anti-invasive activity of parthenolide and 3-isopropyl-2-methyl-4-methyleneisoxazolidin-5-One (MZ-6) - A new compound with α-methylene-γ-lactone motif - On two breast cancer cell lines

Author keywords

Anticancer activity; Gene expression; Metastasis; Sesquiterpene lactones; Wound healing assay

Indexed keywords

3 ISOPROPYL 2 METHYL 4 METHYLENEISOXAZOLIDIN 5 ONE; ANTINEOPLASTIC AGENT; GELATINASE B; MESSENGER RNA; NITROGEN; PARTHENOLIDE; UNCLASSIFIED DRUG; UROKINASE;

EID: 84155188969     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01257.x     Document Type: Article
Times cited : (19)

References (34)
  • 1
    • 0021921867 scopus 로고
    • Synthesis and biological activity of alfa-methylene-gamma-butyrolactones
    • Hoffmann H.M.R., Rabe J. (1985) Synthesis and biological activity of alfa-methylene-gamma-butyrolactones. Angew Chem Int Ed Engl;24:94-110.
    • (1985) Angew Chem Int Ed Engl , vol.24 , pp. 94-110
    • Hoffmann, H.M.R.1    Rabe, J.2
  • 2
    • 18444367100 scopus 로고    scopus 로고
    • Anti-cancer potential of sesquiterpene lactones: bioactivity and molecular mechanisms
    • Zhang S., Won Y.K., Ong C.N., Shen H.M. (2005) Anti-cancer potential of sesquiterpene lactones: bioactivity and molecular mechanisms. Curr Med Chem Anticancer Agents;5:239-249.
    • (2005) Curr Med Chem Anticancer Agents , vol.5 , pp. 239-249
    • Zhang, S.1    Won, Y.K.2    Ong, C.N.3    Shen, H.M.4
  • 3
    • 0036783038 scopus 로고    scopus 로고
    • Antiproliferative sesquiterpene lactones from the roots of Inula helenium
    • Konishi T., Shimada Y., Nagao T., Okabe H., Konoshima T. (2002) Antiproliferative sesquiterpene lactones from the roots of Inula helenium. Biol Pharm Bull;25:1370-1372.
    • (2002) Biol Pharm Bull , vol.25 , pp. 1370-1372
    • Konishi, T.1    Shimada, Y.2    Nagao, T.3    Okabe, H.4    Konoshima, T.5
  • 4
    • 4344588130 scopus 로고    scopus 로고
    • Chemopreventive activity of parthenolide against UVB-induced skin cancer and its mechanisms
    • Won Y.K., Ong C.N., Shi X., Shen H.M. (2004) Chemopreventive activity of parthenolide against UVB-induced skin cancer and its mechanisms. Carcinogenesis;25:1449-1458.
    • (2004) Carcinogenesis , vol.25 , pp. 1449-1458
    • Won, Y.K.1    Ong, C.N.2    Shi, X.3    Shen, H.M.4
  • 5
    • 0034902498 scopus 로고    scopus 로고
    • The influence of glutathione and cysteine levels on the cytotoxicity of helenanolide type sesquiterpene lactones against KB cells
    • Heilmann J., Wasescha M.R., Schmidt T.J. (2001) The influence of glutathione and cysteine levels on the cytotoxicity of helenanolide type sesquiterpene lactones against KB cells. Bioorg Med Chem;9:2189-2194.
    • (2001) Bioorg Med Chem , vol.9 , pp. 2189-2194
    • Heilmann, J.1    Wasescha, M.R.2    Schmidt, T.J.3
  • 6
    • 0029311312 scopus 로고
    • Feverfew: chemistry and biological activity
    • Knight D.W. (1995) Feverfew: chemistry and biological activity. Nat Prod Rep;12:271-276.
    • (1995) Nat Prod Rep , vol.12 , pp. 271-276
    • Knight, D.W.1
  • 7
    • 2442538125 scopus 로고    scopus 로고
    • Critical roles of intracellular thiols and calcium in parthenolide-induced apoptosis in human colorectal cancer cells
    • Zhang S., Ong C.N., Shen H.M. (2004) Critical roles of intracellular thiols and calcium in parthenolide-induced apoptosis in human colorectal cancer cells. Cancer Lett;208:143-153.
    • (2004) Cancer Lett , vol.208 , pp. 143-153
    • Zhang, S.1    Ong, C.N.2    Shen, H.M.3
  • 8
    • 15744396281 scopus 로고    scopus 로고
    • A potent apoptosis-inducing activity of a sesquiterpene lactone, arucanolide, in HL60 cells: a crucial role of apoptosis-inducing factor
    • Nakagawa Y., Iinuma M., Matsuura N., Yi K., Naoi M., Nakayama T., Nozawa Y., Akao Y. (2005) A potent apoptosis-inducing activity of a sesquiterpene lactone, arucanolide, in HL60 cells: a crucial role of apoptosis-inducing factor. J Pharmacol Sci;97:242-252.
    • (2005) J Pharmacol Sci , vol.97 , pp. 242-252
    • Nakagawa, Y.1    Iinuma, M.2    Matsuura, N.3    Yi, K.4    Naoi, M.5    Nakayama, T.6    Nozawa, Y.7    Akao, Y.8
  • 9
    • 0344737710 scopus 로고    scopus 로고
    • Potent induction of apoptosis by germacranolide sesquiterpene lactones on human myeloid leukemia cells
    • Rivero A., Quintana J., Eiroa J.L., Lopez M., Triana J., Bermejo J., Estévez F. (2003) Potent induction of apoptosis by germacranolide sesquiterpene lactones on human myeloid leukemia cells. Eur J Pharmacol;482:77-84.
    • (2003) Eur J Pharmacol , vol.482 , pp. 77-84
    • Rivero, A.1    Quintana, J.2    Eiroa, J.L.3    Lopez, M.4    Triana, J.5    Bermejo, J.6    Estévez, F.7
  • 10
    • 0035422774 scopus 로고    scopus 로고
    • Helenalin triggers a CD95 death receptor-independent apoptosis that is not affected by overexpression of Bcl-x(L) or Bcl-2
    • Dirsch V.M., Stuppner H., Vollmar A.M. (2001) Helenalin triggers a CD95 death receptor-independent apoptosis that is not affected by overexpression of Bcl-x(L) or Bcl-2. Cancer Res;61:5817-5823.
    • (2001) Cancer Res , vol.61 , pp. 5817-5823
    • Dirsch, V.M.1    Stuppner, H.2    Vollmar, A.M.3
  • 11
    • 0037064130 scopus 로고    scopus 로고
    • Oxidative stress-mediated apoptosis. The anticancer effect of the sesquiterpene lactone parthenolide
    • Wen J., You K.R., Lee S.Y., Song C.H., Kim D.G. (2002) Oxidative stress-mediated apoptosis. The anticancer effect of the sesquiterpene lactone parthenolide. J Biol Chem;277:38954-38964.
    • (2002) J Biol Chem , vol.277 , pp. 38954-38964
    • Wen, J.1    You, K.R.2    Lee, S.Y.3    Song, C.H.4    Kim, D.G.5
  • 12
  • 14
    • 0033571108 scopus 로고    scopus 로고
    • The antiinflammatory sesquiterpene lactone parthenolide inhibits NF-kappa B by targeting the I kappa B kinase complex
    • Hehner S.P., Hofmann T.G., Droge W., Schmitz M.L. (1999) The antiinflammatory sesquiterpene lactone parthenolide inhibits NF-kappa B by targeting the I kappa B kinase complex. J Immunol;163:5617-5623.
    • (1999) J Immunol , vol.163 , pp. 5617-5623
    • Hehner, S.P.1    Hofmann, T.G.2    Droge, W.3    Schmitz, M.L.4
  • 15
    • 34249892217 scopus 로고    scopus 로고
    • Parthenolide inhibits IkappaB kinase, NF-kappaB activation, and inflammatory response in cystic fibrosis cells and mice
    • Saadane A., Masters S., DiDonato J., Li J., Berger M. (2007) Parthenolide inhibits IkappaB kinase, NF-kappaB activation, and inflammatory response in cystic fibrosis cells and mice. Am J Respir Cell Mol Biol;36:728-736.
    • (2007) Am J Respir Cell Mol Biol , vol.36 , pp. 728-736
    • Saadane, A.1    Masters, S.2    DiDonato, J.3    Li, J.4    Berger, M.5
  • 16
    • 48449083208 scopus 로고    scopus 로고
    • Molecular basis of parthenolide-dependent proapoptotic activity in cancer cells
    • Pajak B., Gajkowska B., Orzechowski A. (2008) Molecular basis of parthenolide-dependent proapoptotic activity in cancer cells. Folia Histochem Cytobiol;46:129-135.
    • (2008) Folia Histochem Cytobiol , vol.46 , pp. 129-135
    • Pajak, B.1    Gajkowska, B.2    Orzechowski, A.3
  • 17
    • 31444446499 scopus 로고    scopus 로고
    • 4-Methylideneisoxazolidin-5-ones - a new class of alpha-methylidene-gamma-lactones with high cytostatic activity
    • Janecki T., Wasek T., Rozalski M., Krajewska U., Studzian K., Janecka A. (2006) 4-Methylideneisoxazolidin-5-ones - a new class of alpha-methylidene-gamma-lactones with high cytostatic activity. Bioorg Med Chem Lett;16:1430-1433.
    • (2006) Bioorg Med Chem Lett , vol.16 , pp. 1430-1433
    • Janecki, T.1    Wasek, T.2    Rozalski, M.3    Krajewska, U.4    Studzian, K.5    Janecka, A.6
  • 18
    • 33847166620 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of 4-methylideneisoxazolidin-5-ones - a new class of highly cytotoxic alpha-methylidene-gamma-lactones
    • Rozalski M., Krajewska U., Panczyk M., Mirowski M., Rozalska B., Wasek T., Janecki T. (2007) Synthesis and biological evaluation of 4-methylideneisoxazolidin-5-ones - a new class of highly cytotoxic alpha-methylidene-gamma-lactones. Eur J Med Chem;42:248-255.
    • (2007) Eur J Med Chem , vol.42 , pp. 248-255
    • Rozalski, M.1    Krajewska, U.2    Panczyk, M.3    Mirowski, M.4    Rozalska, B.5    Wasek, T.6    Janecki, T.7
  • 19
    • 27944442776 scopus 로고    scopus 로고
    • Knoevenagel reaction of diethylphosphonoacetic acid: a facile route to diethyl (E)-2-arylvinylphosphonates
    • Krawczyk H., Albrecht Ł. (2005) Knoevenagel reaction of diethylphosphonoacetic acid: a facile route to diethyl (E)-2-arylvinylphosphonates. Synthesis;2005:2887-2896.
    • (2005) Synthesis , vol.2005 , pp. 2887-2896
    • Krawczyk, H.1    Albrecht, Ł.2
  • 20
    • 0027270211 scopus 로고
    • Characterization of the cellular reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT): subcellular localization, substrate dependence, and involvement of mitochondrial electrontransport in MTT reduction
    • Berridge M.V., Tan A.S. (1993) Characterization of the cellular reduction of 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT): subcellular localization, substrate dependence, and involvement of mitochondrial electrontransport in MTT reduction. Arch Biochem Biophys;303:474-482.
    • (1993) Arch Biochem Biophys , vol.303 , pp. 474-482
    • Berridge, M.V.1    Tan, A.S.2
  • 21
    • 0030852948 scopus 로고    scopus 로고
    • Mechanism of cellular 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) reduction
    • Liu Y., Peterson D.A., Kimura H., Schubert D. (1997) Mechanism of cellular 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) reduction. J Neurochem;69:581-593.
    • (1997) J Neurochem , vol.69 , pp. 581-593
    • Liu, Y.1    Peterson, D.A.2    Kimura, H.3    Schubert, D.4
  • 23
    • 68649128083 scopus 로고    scopus 로고
    • Gene expression of the invasive phenotype of TNF-a-treated MCF-7 cells
    • Yin Y., Chen X., Shu Y. (2009) Gene expression of the invasive phenotype of TNF-a-treated MCF-7 cells. Biomed Pharmacother;63:421-428.
    • (2009) Biomed Pharmacother , vol.63 , pp. 421-428
    • Yin, Y.1    Chen, X.2    Shu, Y.3
  • 24
    • 0036203856 scopus 로고    scopus 로고
    • Activity of type IV collagenases (MMP-2 and MMP-9) in primary pulmonary carcinomas: a quantitative analysis
    • Hrabec E., Strek M., Nowak D., Greger J., Suwalski M., Hrabec Z. (2002) Activity of type IV collagenases (MMP-2 and MMP-9) in primary pulmonary carcinomas: a quantitative analysis. J Cancer Res Clin Oncol;128:197-204.
    • (2002) J Cancer Res Clin Oncol , vol.128 , pp. 197-204
    • Hrabec, E.1    Strek, M.2    Nowak, D.3    Greger, J.4    Suwalski, M.5    Hrabec, Z.6
  • 25
    • 73249124562 scopus 로고    scopus 로고
    • The renaissance of α-methylene-γ-butyrolactones: new synthetic approaches
    • Kitson R.R.A., Millemaggi A., Taylor R.J.K. (2009) The renaissance of α-methylene-γ-butyrolactones: new synthetic approaches. Angew Chem Int Ed;48:9426-9451.
    • (2009) Angew Chem Int Ed , vol.48 , pp. 9426-9451
    • Kitson, R.R.A.1    Millemaggi, A.2    Taylor, R.J.K.3
  • 26
    • 79955855985 scopus 로고    scopus 로고
    • Recent advances in the synthesis of α-alkylidene-δ-lactones, α-alkylidene-γ-lactams and α-alkylidene-δ-lactams
    • Albrecht A., Albrecht Ł., Janecki T. (2011) Recent advances in the synthesis of α-alkylidene-δ-lactones, α-alkylidene-γ-lactams and α-alkylidene-δ-lactams. Eur J Org Chem;2011:2747-2766.
    • (2011) Eur J Org Chem , vol.2011 , pp. 2747-2766
    • Albrecht, A.1    Albrecht, Ł.2    Janecki, T.3
  • 27
    • 41849150003 scopus 로고    scopus 로고
    • Metastasis: a therapeutic target for cancer
    • Steeg P.S., Theodorescu D. (2008) Metastasis: a therapeutic target for cancer. Nat Clin Pract Oncol;5:206-219.
    • (2008) Nat Clin Pract Oncol , vol.5 , pp. 206-219
    • Steeg, P.S.1    Theodorescu, D.2
  • 29
    • 0038236716 scopus 로고    scopus 로고
    • The basement membrane matrix in malignancy
    • Engbring J.A., Kleinman H.K. (2003) The basement membrane matrix in malignancy. J Pathol;200:465-470.
    • (2003) J Pathol , vol.200 , pp. 465-470
    • Engbring, J.A.1    Kleinman, H.K.2
  • 30
    • 33846120227 scopus 로고    scopus 로고
    • Mechanisms of metastasis and molecular markers of malignant tumor progression. I. Colorectal cancer
    • Widel M.S., Widel M. (2006) Mechanisms of metastasis and molecular markers of malignant tumor progression. I. Colorectal cancer. Postepy Hig Med Dosw (Online);60:453-470.
    • (2006) Postepy Hig Med Dosw (Online) , vol.60 , pp. 453-470
    • Widel, M.S.1    Widel, M.2
  • 32
    • 39149084984 scopus 로고    scopus 로고
    • Rapid expression and activation of MMP-2 and MMP-9 upon exposure of human breast cancer cells (MCF-7) to fibronectin in serum free medium
    • Das S., Banerji A., Frei E., Chatterjee A. (2008) Rapid expression and activation of MMP-2 and MMP-9 upon exposure of human breast cancer cells (MCF-7) to fibronectin in serum free medium. Life Sci;82:467-476.
    • (2008) Life Sci , vol.82 , pp. 467-476
    • Das, S.1    Banerji, A.2    Frei, E.3    Chatterjee, A.4
  • 33
    • 0347917028 scopus 로고    scopus 로고
    • The urokinase plasminogen activator system: role in malignancy
    • Duffy M.J. (2004) The urokinase plasminogen activator system: role in malignancy. Curr Pharm Des;10:39-49.
    • (2004) Curr Pharm Des , vol.10 , pp. 39-49
    • Duffy, M.J.1
  • 34
    • 3042685205 scopus 로고    scopus 로고
    • The urokinase plasminogen activator system: a rich source of tumour markers for the individualized management of patients with cancer
    • Duffy M.J., Duggan C. (2004) The urokinase plasminogen activator system: a rich source of tumour markers for the individualized management of patients with cancer. Clin Biochem;37:541-548.
    • (2004) Clin Biochem , vol.37 , pp. 541-548
    • Duffy, M.J.1    Duggan, C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.