메뉴 건너뛰기




Volumn 18, Issue 12, 2013, Pages 15750-15768

Design, synthesis and evaluation of N13-substituted evodiamine derivatives against human cancer cell lines

Author keywords

Antitumor activity; Apoptosis; N13 substituted evodiamine derivatives; Solubility

Indexed keywords

ANTINEOPLASTIC AGENT; EVODIAMINE; QUINAZOLINE DERIVATIVE;

EID: 84890899778     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules181215750     Document Type: Article
Times cited : (24)

References (35)
  • 1
    • 84874609274 scopus 로고    scopus 로고
    • Pharmacological actions of multi-target-directed evodiamine
    • Yu, H.; Jin, H.; Gong, W.; Wang, Z.; Liang, H. Pharmacological actions of multi-target-directed evodiamine. Molecules 2013, 18, 1826-1843.
    • (2013) Molecules , vol.18 , pp. 1826-1843
    • Yu, H.1    Jin, H.2    Gong, W.3    Wang, Z.4    Liang, H.5
  • 2
    • 84890956145 scopus 로고    scopus 로고
    • Traditional Chinese Medicine Composition for Treating Greasy Food Regurgitation [Machine Translation]
    • Chen, B.-Y.; Qiu, T. Traditional Chinese Medicine Composition for Treating Greasy Food Regurgitation [Machine Translation]. Patent CN 103301272 A, 18 September 2012.
    • (2012) Patent CN 103301272 A, 18 September
    • Chen, B.-Y.1    Qiu, T.2
  • 3
    • 84890938025 scopus 로고
    • A Hair Nourishing and Hair Growth Promoting Food Prepared from Evodia rutaecarpa benth (Evodiae fructus) or Evodia rutaecarpa benth var Officinalis Huang Belonging to Rutaceae
    • Juchi, S.; Uchida, Y. A Hair Nourishing and Hair Growth Promoting Food Prepared from Evodia rutaecarpa benth (Evodiae fructus) or Evodia rutaecarpa benth var Officinalis Huang Belonging to Rutaceae. Patent JP 61001619, 1986.
    • (1986) Patent JP 61001619
    • Juchi, S.1    Uchida, Y.2
  • 4
    • 67249138744 scopus 로고    scopus 로고
    • Evodiamine: A novel anti-cancer alkaloid from evodia rutaecarpa
    • Jiang, J.; Hu, C. Evodiamine: A novel anti-cancer alkaloid from evodia rutaecarpa. Molecules 2009, 14, 1852-1859.
    • (2009) Molecules , vol.14 , pp. 1852-1859
    • Jiang, J.1    Hu, C.2
  • 5
    • 84870364791 scopus 로고    scopus 로고
    • Evodiamine inhibits STAT3 signaling by inducing phosphatase shatterproof i in hepatocellular carcinoma cells
    • Yang, J.; Cai, X.; Lu, W.; Hu, C.; Xu, X.; Yu, Q.; Cao, P. Evodiamine inhibits STAT3 signaling by inducing phosphatase shatterproof I in hepatocellular carcinoma cells. Cancer Lett. 2013, 328, 243-251.
    • (2013) Cancer Lett. , vol.328 , pp. 243-251
    • Yang, J.1    Cai, X.2    Lu, W.3    Hu, C.4    Xu, X.5    Yu, Q.6    Cao, P.7
  • 6
    • 84872078830 scopus 로고    scopus 로고
    • Topoisomerase i inhibitor evodiamine acts as an antibacterial agent against drug-resistant Klebsiella pneumoniae
    • Wu, J.-Y.; Chang, M.-C.; Chen, C.-S.; Lin, H.-C.; Tsai, H.-P.; Yang, C.-C.; Yang, C.-H.; Lin, C.-M. Topoisomerase I inhibitor evodiamine acts as an antibacterial agent against drug-resistant Klebsiella pneumoniae. Planta Med. 2013, 79, 27-29.
    • (2013) Planta Med. , vol.79 , pp. 27-29
    • Wu, J.-Y.1    Chang, M.-C.2    Chen, C.-S.3    Lin, H.-C.4    Tsai, H.-P.5    Yang, C.-C.6    Yang, C.-H.7    Lin, C.-M.8
  • 8
    • 84876087744 scopus 로고    scopus 로고
    • Targeting apoptosis pathways in cancer by Chinese medicine
    • Li-Weber, M. Targeting apoptosis pathways in cancer by Chinese medicine. Cancer Lett. 2013, 332, 304-312.
    • (2013) Cancer Lett. , vol.332 , pp. 304-312
    • Li-Weber, M.1
  • 11
    • 84863252809 scopus 로고    scopus 로고
    • Cytotoxic effect of evodiamine in SGC-7901 human gastric adenocarcinoma cells via simultaneous induction of apoptosis and autophagy
    • Rasul, A.; Yu, B.; Zhong, L.; Khan, M.; Yang, H.; Ma, T. Cytotoxic effect of evodiamine in SGC-7901 human gastric adenocarcinoma cells via simultaneous induction of apoptosis and autophagy. Oncol. Rep. 2012, 27, 1481-1487.
    • (2012) Oncol. Rep. , vol.27 , pp. 1481-1487
    • Rasul, A.1    Yu, B.2    Zhong, L.3    Khan, M.4    Yang, H.5    Ma, T.6
  • 12
    • 84862790283 scopus 로고    scopus 로고
    • Evodiamine, a dual catalytic inhibitor of type i and II topoisomerases, exhibits enhanced inhibition against camptothecin resistant cells
    • Pan, X.; Hartley, J.M.; Hartley, J.A.; White, K.N.; Wang, Z.; Bligh, S.W. A. Evodiamine, a dual catalytic inhibitor of type I and II topoisomerases, exhibits enhanced inhibition against camptothecin resistant cells. Phytomedicine 2012, 19, 618-624.
    • (2012) Phytomedicine , vol.19 , pp. 618-624
    • Pan, X.1    Hartley, J.M.2    Hartley, J.A.3    White, K.N.4    Wang, Z.5    Bligh, S.W.A.6
  • 13
    • 78149253942 scopus 로고    scopus 로고
    • Selection of evodiamine as a novel topoisomerase i inhibitor by structure-based virtual screening and hit optimization of evodiamine derivatives as antitumor agents
    • Dong, G.; Sheng, C.; Wang, S.; Miao, Z.; Yao, J.; Zhang, W. Selection of evodiamine as a novel topoisomerase I inhibitor by structure-based virtual screening and hit optimization of evodiamine derivatives as antitumor agents. J. Med. Chem. 2010, 53, 7521-7531.
    • (2010) J. Med. Chem. , vol.53 , pp. 7521-7531
    • Dong, G.1    Sheng, C.2    Wang, S.3    Miao, Z.4    Yao, J.5    Zhang, W.6
  • 14
    • 77955226921 scopus 로고    scopus 로고
    • Evodiamine induces caspase-dependent apoptosis and S phase arrest in human colon loVo cells
    • Zhang, C.; Fan, X.; Xu, X.; Yang, X.; Wang, X.; Liang, H.-P. Evodiamine induces caspase-dependent apoptosis and S phase arrest in human colon loVo cells. Anti-Cancer Drugs 2010, 21, 766-776.
    • (2010) Anti-Cancer Drugs , vol.21 , pp. 766-776
    • Zhang, C.1    Fan, X.2    Xu, X.3    Yang, X.4    Wang, X.5    Liang, H.-P.6
  • 15
    • 77649178970 scopus 로고    scopus 로고
    • Evodiamine-induced human melanoma A375-S2 cell death was mediated by PI3K/Akt/caspase and Fas-L/NF-κB signaling pathways and augmented by ubiquitin-proteasome inhibition
    • Wang, C.; Li, S.; Wang, M. Evodiamine-induced human melanoma A375-S2 cell death was mediated by PI3K/Akt/caspase and Fas-L/NF-κB signaling pathways and augmented by ubiquitin-proteasome inhibition. Toxicol. In Vitro 2010, 24, 898-904.
    • (2010) Toxicol. in Vitro , vol.24 , pp. 898-904
    • Wang, C.1    Li, S.2    Wang, M.3
  • 16
    • 84866328968 scopus 로고    scopus 로고
    • New tricks for an old natural product: Discovery of highly potent evodiamine derivatives as novel antitumor agents by systemic structure-activity relationship analysis and biological evaluations
    • Dong, G.; Wang, S.; Miao, Z.; Yao, J.; Zhang, Y.; Guo, Z.; Zhang, W.; Sheng, C. New tricks for an old natural product: Discovery of highly potent evodiamine derivatives as novel antitumor agents by systemic structure-activity relationship analysis and biological evaluations. J. Med. Chem. 2012, 55, 7593-7613.
    • (2012) J. Med. Chem. , vol.55 , pp. 7593-7613
    • Dong, G.1    Wang, S.2    Miao, Z.3    Yao, J.4    Zhang, Y.5    Guo, Z.6    Zhang, W.7    Sheng, C.8
  • 18
    • 67650156103 scopus 로고    scopus 로고
    • Antiproliferation and apoptosis induced by evodiamine in human Colorectal carcinoma cells (COLO-205)
    • Yang, Z.-G.; Chen, A.Q.; Liu, B. Antiproliferation and apoptosis induced by evodiamine in human Colorectal carcinoma cells (COLO-205). Chem. Biodivers. 2009, 6, 924-933.
    • (2009) Chem. Biodivers. , vol.6 , pp. 924-933
    • Yang, Z.-G.1    Chen, A.Q.2    Liu, B.3
  • 19
    • 71749101583 scopus 로고    scopus 로고
    • Evodiamine inhibits adipogenesis via the EGFR-PKCalpha-ERK signaling pathway
    • Wang, T.; Wang, Y.; Yamashita, H. Evodiamine inhibits adipogenesis via the EGFR-PKCalpha-ERK signaling pathway. FEBS Lett. 2009, 583, 3655-3659.
    • (2009) FEBS Lett. , vol.583 , pp. 3655-3659
    • Wang, T.1    Wang, Y.2    Yamashita, H.3
  • 20
    • 66349130754 scopus 로고    scopus 로고
    • Evodiamine stabilizes topoisomerase I-DNA cleavable complex to inhibit topoisomerase i activity
    • Chan, A.L.F.; Chang, W.-S.; Chen, L.-M.; Lee, C.-M.; Chen, C.-E.; Lin, C.-M.; Hwang, J.-L. Evodiamine stabilizes topoisomerase I-DNA cleavable complex to inhibit topoisomerase I activity. Molecules 2009, 14, 1342-1352.
    • (2009) Molecules , vol.14 , pp. 1342-1352
    • Chan, A.L.F.1    Chang, W.-S.2    Chen, L.-M.3    Lee, C.-M.4    Chen, C.-E.5    Lin, C.-M.6    Hwang, J.-L.7
  • 21
    • 34247498234 scopus 로고    scopus 로고
    • Anti-proliferative effects of evodiamine on human prostate cancer cell lines DU145 and PC3
    • Kan, S.-F.; Yu, C.-H.; Pu, H.-F.; Hsu, J.-M.; Chen, M.-J.; Wang, P.S. Anti-proliferative effects of evodiamine on human prostate cancer cell lines DU145 and PC3. J. Cell. Biochem. 2007, 101, 44-56.
    • (2007) J. Cell. Biochem. , vol.101 , pp. 44-56
    • Kan, S.-F.1    Yu, C.-H.2    Pu, H.-F.3    Hsu, J.-M.4    Chen, M.-J.5    Wang, P.S.6
  • 22
    • 33645223907 scopus 로고    scopus 로고
    • Evodiamine inhibits in vitro angiogenesis: Implication for antitumorgenicity
    • Shyu, K.-G.; Lin, S.; Lee, C.-C.; Chen, E.; Lin, L.-C.; Wang, B.-W.; Tsai, S.-C. Evodiamine inhibits in vitro angiogenesis: Implication for antitumorgenicity. Life Sci. 2006, 78, 2234-2243.
    • (2006) Life Sci. , vol.78 , pp. 2234-2243
    • Shyu, K.-G.1    Lin, S.2    Lee, C.-C.3    Chen, E.4    Lin, L.-C.5    Wang, B.-W.6    Tsai, S.-C.7
  • 23
    • 19844377252 scopus 로고    scopus 로고
    • Antitumor mechanism of evodiamine, a constituent from Chinese herb evodiae fructus, in human multiple-drug resistant breast cancer NCI/ADR-RES cells in vitro and in vivo
    • Liao, C.H.; Pan, S.L.; Guh, J.H.; Chang, Y.L.; Pai, H.C.; Lin, C.H.; Teng, C.M. Antitumor mechanism of evodiamine, a constituent from Chinese herb evodiae fructus, in human multiple-drug resistant breast cancer NCI/ADR-RES cells in vitro and in vivo. Carcinogenesis 2005, 26, 968-975.
    • (2005) Carcinogenesis , vol.26 , pp. 968-975
    • Liao, C.H.1    Pan, S.L.2    Guh, J.H.3    Chang, Y.L.4    Pai, H.C.5    Lin, C.H.6    Teng, C.M.7
  • 24
    • 84871544584 scopus 로고    scopus 로고
    • Design, synthesis and in vitro and in vivo antitumor activities of novel bivalent β-carbolines
    • Shi, B.; Cao, R.; Fan, W.; Guo, L.; Ma, Q.; Chen, X.; Zhang, G.; Qiu, L.; Song, H. Design, synthesis and in vitro and in vivo antitumor activities of novel bivalent β-carbolines. Eur. J. Med. Chem. 2013, 60, 10-22.
    • (2013) Eur. J. Med. Chem. , vol.60 , pp. 10-22
    • Shi, B.1    Cao, R.2    Fan, W.3    Guo, L.4    Ma, Q.5    Chen, X.6    Zhang, G.7    Qiu, L.8    Song, H.9
  • 25
    • 79957837488 scopus 로고    scopus 로고
    • Synthesis and cytotoxicity of 17a-aza-D-homo-androster-17-one derivatives
    • Huang, Y.; Cui, J.; Zhong, Z.; Gan, C.; Zhang, W.; Song, H. Synthesis and cytotoxicity of 17a-aza-D-homo-androster-17-one derivatives. Bioorg. Med. Chem. Lett. 2011, 21, 3641-3643.
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 3641-3643
    • Huang, Y.1    Cui, J.2    Zhong, Z.3    Gan, C.4    Zhang, W.5    Song, H.6
  • 26
    • 80053185089 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of 1,9-disubstituted β-carbolines as potent DNA intercalating and cytotoxic agents
    • Chen, Z.; Cao, R.; Shi, B.; Guo, L.; Sun, J.; Ma, Q.; Fan, W.; Song, H. Synthesis and biological evaluation of 1,9-disubstituted β-carbolines as potent DNA intercalating and cytotoxic agents. Eur. J. Med. Chem. 2011, 46, 5127-5137.
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 5127-5137
    • Chen, Z.1    Cao, R.2    Shi, B.3    Guo, L.4    Sun, J.5    Ma, Q.6    Fan, W.7    Song, H.8
  • 27
    • 77957835162 scopus 로고    scopus 로고
    • Synthesis and cytotoxic evaluation of 1-carboxamide and 1-amino side chain substituted β-carbolines
    • Ma, C.; Cao, R.; Shi, B.; Zhou, X.; Ma, Q.; Sun, J.; Guo, L.; Yi, W.; Chen, Z.; Song, H. Synthesis and cytotoxic evaluation of 1-carboxamide and 1-amino side chain substituted β-carbolines. Eur. J. Med. Chem. 2010, 45, 5513-5519.
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 5513-5519
    • Ma, C.1    Cao, R.2    Shi, B.3    Zhou, X.4    Ma, Q.5    Sun, J.6    Guo, L.7    Yi, W.8    Chen, Z.9    Song, H.10
  • 28
    • 77954313859 scopus 로고    scopus 로고
    • Synthesis of novel β-carbolines with efficient DNA-binding capacity and potent cytotoxicity
    • Chen, Z.; Cao, R.; Shi, B.; Yi, W.; Yu, L.; Song, H.; Ren, Z.; Peng, W. Synthesis of novel β-carbolines with efficient DNA-binding capacity and potent cytotoxicity. Bioorg. Med. Chem. Lett. 2010, 20, 3876-3879.
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 3876-3879
    • Chen, Z.1    Cao, R.2    Shi, B.3    Yi, W.4    Yu, L.5    Song, H.6    Ren, Z.7    Peng, W.8
  • 29
    • 84880775813 scopus 로고    scopus 로고
    • Synthesis and evaluation of some 17-acetamidoandrostane and N,N-dimethyl-7-deoxycholic amide derivatives as cytotoxic agents: Structure/activity studies
    • Huang, Y.; Cui, J.; Jia, L.; Gan, C.; Song, H.; Zeng, C.; Zhou, A. Synthesis and evaluation of some 17-acetamidoandrostane and N,N-dimethyl-7- deoxycholic amide derivatives as cytotoxic agents: Structure/activity studies. Molecules 2013, 18, 7436-7447.
    • (2013) Molecules , vol.18 , pp. 7436-7447
    • Huang, Y.1    Cui, J.2    Jia, L.3    Gan, C.4    Song, H.5    Zeng, C.6    Zhou, A.7
  • 30
    • 84890962520 scopus 로고    scopus 로고
    • PerkinElmer: Waltham, MA, USA, (accessed on 21 November 2013)
    • ChemBioDraw Ultra 11.0. PerkinElmer: Waltham, MA, USA, 2013. Available online: http://www.cambridgesoft.com (accessed on 21 November 2013).
    • (2013) ChemBioDraw Ultra 11.0
  • 31
    • 0003331354 scopus 로고
    • Simulated Gastric Fluid and Simulated Intestinal Fluid, TS, The United States Pharmacopeial Convention, Inc.: Rockville, MD, USA
    • Simulated Gastric Fluid and Simulated Intestinal Fluid, TS. In The United States Pharmacopeia 23, the National Formulary 18; The United States Pharmacopeial Convention, Inc.: Rockville, MD, USA, 1995; p. 2053.
    • (1995) The United States Pharmacopeia 23, the National Formulary 18 , pp. 2053
  • 32
    • 70349833199 scopus 로고    scopus 로고
    • Determination of drug-like properties of a novel antileishmanial compound: In vitro absorption, distribution, metabolism, and excretion studies
    • Mondal, S.K.; Mondal, N.B.; Banerjee, S.; Mazumder, U.K. Determination of drug-like properties of a novel antileishmanial compound: In vitro absorption, distribution, metabolism, and excretion studies. Indian J. Pharmacol. 2009, 41, 176-181.
    • (2009) Indian J. Pharmacol. , vol.41 , pp. 176-181
    • Mondal, S.K.1    Mondal, N.B.2    Banerjee, S.3    Mazumder, U.K.4
  • 33
    • 34247574645 scopus 로고    scopus 로고
    • Synthesis and evaluation of mutual prodrugs of isoniazid, p-amino salicylic acid and ethambutol
    • Rawat, J.; Jain, P.K.; Ravichandran, V.; Agrawal, R.K. Synthesis and evaluation of mutual prodrugs of isoniazid, p-amino salicylic acid and ethambutol. ARKIVOC 2007, 1, 105-118.
    • (2007) ARKIVOC , vol.1 , pp. 105-118
    • Rawat, J.1    Jain, P.K.2    Ravichandran, V.3    Agrawal, R.K.4
  • 34
    • 84890936752 scopus 로고    scopus 로고
    • Dissolution method developmeng for gastro retentive controlled releave cephalaxin tablet
    • Lokhande, P.; Gite, S.; Sakarkar, D.M. Dissolution method developmeng for gastro retentive controlled releave cephalaxin tablet. Int. Res. J. Pharm. 2012, 3, 244-247.
    • (2012) Int. Res. J. Pharm. , vol.3 , pp. 244-247
    • Lokhande, P.1    Gite, S.2    Sakarkar, D.M.3
  • 35
    • 84874507594 scopus 로고    scopus 로고
    • HFormulation and evaluation of Piroxicam liquisolid compacts
    • Ahmed, S.A.J.; Ahmed, A. HFormulation and evaluation of Piroxicam liquisolid compacts. Int. J. Pharm. Pharm. Sci. 2013, 5, 132-141.
    • (2013) Int. J. Pharm. Pharm. Sci. , vol.5 , pp. 132-141
    • Ahmed, S.A.J.1    Ahmed, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.