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Volumn 9, Issue 1, 2014, Pages 164-173

Discovery of potent parthenolide-based antileukemic agents enabled by late-stage P450-Mediated C-H functionalization

Author keywords

[No Author keywords available]

Indexed keywords

ANTILEUKEMIC AGENT; CYTOCHROME P450; PARTHENOLIDE; CARBON; HYDROGEN;

EID: 84899641647     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb400626     Document Type: Article
Times cited : (94)

References (63)
  • 2
    • 84861633609 scopus 로고    scopus 로고
    • Natural and synthetic α-methylenelactones and α- methylenelactams with anticancer potential
    • Janecka, A., Wyrebska, A., Gach, K., Fichna, J., and Janecki, T. (2012) Natural and synthetic α-methylenelactones and α-methylenelactams with anticancer potential. Drug Discovery Today 17, 561-572.
    • (2012) Drug Discovery Today , vol.17 , pp. 561-572
    • Janecka, A.1    Wyrebska, A.2    Gach, K.3    Fichna, J.4    Janecki, T.5
  • 3
    • 24144443802 scopus 로고    scopus 로고
    • Feverfew: Weeding out the root of leukaemia
    • DOI 10.1517/14712598.5.9.1147
    • Guzman, M. L., and Jordan, C. T. (2005) Feverfew: Weeding out the root of leukaemia. Expert Opin. Biol. Ther. 5, 1147-1152. (Pubitemid 41243350)
    • (2005) Expert Opinion on Biological Therapy , vol.5 , Issue.9 , pp. 1147-1152
    • Guzman, M.L.1    Jordan, C.T.2
  • 4
    • 84865967712 scopus 로고    scopus 로고
    • Sesquiterpene lactones as drugs with multiple targets in cancer treatment: Focus on parthenolide
    • Kreuger, M. R., Grootjans, S., Biavatti, M. W., Vandenabeele, P., and DHerde, K. (2012) Sesquiterpene lactones as drugs with multiple targets in cancer treatment: Focus on parthenolide. Anticancer Drugs 23, 883-896.
    • (2012) Anticancer Drugs , vol.23 , pp. 883-896
    • Kreuger, M.R.1    Grootjans, S.2    Biavatti, M.W.3    Vandenabeele, P.4    Dherde, K.5
  • 5
    • 16844363378 scopus 로고    scopus 로고
    • The sesquiterpene lactone parthenolide induces apoptosis of human acute myelogenous leukemia stem and progenitor cells
    • DOI 10.1182/blood-2004-10-4135
    • Guzman, M. L., Rossi, R. M., Karnischky, L., Li, X. J., Peterson, D. R., Howard, D. S., and Jordan, C. T. (2005) The sesquiterpene lactone parthenolide induces apoptosis of human acute myelogenous leukemia stem and progenitor cells. Blood 105, 4163-4169. (Pubitemid 40720758)
    • (2005) Blood , vol.105 , Issue.11 , pp. 4163-4169
    • Guzman, M.L.1    Rossi, R.M.2    Karnischky, L.3    Li, X.4    Peterson, D.R.5    Howard, D.S.6    Jordan, C.T.7
  • 6
    • 84900465144 scopus 로고    scopus 로고
    • Selective induction of apoptosis in acute myelogenous leukemia stem cells by the novel agent parthenolide
    • Guzman, M. L., Karnischky, L., Li, X. J., Neering, S. J., Rossi, R. M., and Jordan, C. T. (2004) Selective induction of apoptosis in acute myelogenous leukemia stem cells by the novel agent parthenolide. Blood 104, 697a-697
    • (2004) Blood , vol.104
    • Guzman, M.L.1    Karnischky, L.2    Li, X.J.3    Neering, S.J.4    Rossi, R.M.5    Jordan, C.T.6
  • 9
    • 0030789242 scopus 로고    scopus 로고
    • Human acute myeloid leukemia is organized as a hierarchy that originates from a primitive hematopoietic cell
    • DOI 10.1038/nm0797-730
    • Bonnet, D., and Dick, J. E. (1997) Human acute myeloid leukemia is organized as a hierarchy that originates from a primitive hematopoietic cell. Nat. Med 3, 730-737. (Pubitemid 27298715)
    • (1997) Nature Medicine , vol.3 , Issue.7 , pp. 730-737
    • Bonnet, D.1    Dick, J.E.2
  • 11
    • 0036090222 scopus 로고    scopus 로고
    • Primitive, quiescent, Philadelphia-positive stem cells from patients with chronic myeloid leukemia are insensitive to STI571 in vitro
    • Graham, S. M., Jorgensen, H. G., Allan, E., Pearson, C., Alcorn, M. J., Richmond, L., and Holyoake, T. L. (2002) Primitive, quiescent, Philadelphia-positive stem cells from patients with chronic myeloid leukemia are insensitive to STI571 in vitro. Blood 99, 319-325.
    • (2002) Blood , vol.99 , pp. 319-325
    • Graham, S.M.1    Jorgensen, H.G.2    Allan, E.3    Pearson, C.4    Alcorn, M.J.5    Richmond, L.6    Holyoake, T.L.7
  • 12
    • 0034662606 scopus 로고    scopus 로고
    • - progenitor cells have decreased sensitivity to chemotherapy and Fas-induced apoptosis, reduced immunogenicity, and impaired dendritic cell transformation capacities
    • Costello, R. T., Mallet, F., Gaugler, B., Sainty, D., Arnoulet, C., Gastaut, J. A., and Olive, D. (2000) Human acute myeloid leukemia CD34+/CD38-progenitor cells have decreased sensitivity to chemotherapy and Fas-induced apoptosis, reduced immunogenicity, and impaired dendritic cell transformation capacities. Cancer Res. 60, 4403-4411. (Pubitemid 32103618)
    • (2000) Cancer Research , vol.60 , Issue.16 , pp. 4403-4411
    • Costello, R.T.1    Mallet, F.2    Gaugler, B.3    Sainty, D.4    Arnoulet, C.5    Gastaut, J.-A.6    Olive, D.7
  • 15
    • 51649112926 scopus 로고    scopus 로고
    • NF-κB pathway inhibitors preferentially inhibit breast cancer stem-like cells
    • Zhou, J., Zhang, H., Gu, P., Bai, J., Margolick, J. B., and Zhang, Y. (2008) NF-κB pathway inhibitors preferentially inhibit breast cancer stem-like cells. Breast Cancer Res. Treat. 111, 419-427.
    • (2008) Breast Cancer Res. Treat , vol.111 , pp. 419-427
    • Zhou, J.1    Zhang, H.2    Gu, P.3    Bai, J.4    Margolick, J.B.5    Zhang, Y.6
  • 16
    • 67651160513 scopus 로고    scopus 로고
    • Nuclear factor-κB inhibition by parthenolide potentiates the efficacy of Taxol in non-small cell lung cancer in vitro and in vivo
    • Zhang, D., Qiu, L., Jin, X., Guo, Z., and Guo, C. (2009) Nuclear factor-κB inhibition by parthenolide potentiates the efficacy of Taxol in non-small cell lung cancer in vitro and in vivo. Mol. Cancer Res. 7, 1139-1149.
    • (2009) Mol. Cancer Res , vol.7 , pp. 1139-1149
    • Zhang, D.1    Qiu, L.2    Jin, X.3    Guo, Z.4    Guo, C.5
  • 17
    • 65549140597 scopus 로고    scopus 로고
    • Effects of the sesquiterpene lactone parthenolide on prostate tumor-initiating cells: An integrated molecular profiling approach
    • Kawasaki, B. T., Hurt, E. M., Kalathur, M., Duhagon, M. A., Milner, J. A., Kim, Y. S., and Farrar, W. L. (2009) Effects of the sesquiterpene lactone parthenolide on prostate tumor-initiating cells: An integrated molecular profiling approach. Prostate 69, 827-837.
    • (2009) Prostate , vol.69 , pp. 827-837
    • Kawasaki, B.T.1    Hurt, E.M.2    Kalathur, M.3    Duhagon, M.A.4    Milner, J.A.5    Kim, Y.S.6    Farrar, W.L.7
  • 18
    • 0037064130 scopus 로고    scopus 로고
    • Oxidative stress-mediated apoptosis: The anticancer effect of the sesquiterpene lactone parthenolide
    • DOI 10.1074/jbc.M203842200
    • Wen, J., You, K. R., Lee, S. Y., Song, C. H., and Kim, D. G. (2002) Oxidative stress-mediated apoptosis. The anticancer effect of the sesquiterpene lactone parthenolide. J. Biol. Chem. 277, 38954-38964. (Pubitemid 35154761)
    • (2002) Journal of Biological Chemistry , vol.277 , Issue.41 , pp. 38954-38964
    • Wen, J.1    You, K.-R.2    Lee, S.-Y.3    Song, C.-H.4    Kim, D.-G.5
  • 19
    • 16844374151 scopus 로고    scopus 로고
    • Identification of the genes involved in enhanced fenretinide-induced apoptosis by parthenolide in human hepatoma cells
    • DOI 10.1158/0008-5472.CAN-04-2221
    • Park, J. H., Liu, L., Kim, I. H., Kim, J. H., You, K. R., and Kim, D. G. (2005) Identification of the genes involved in enhanced fenretinideinduced apoptosis by parthenolide in human hepatoma cells. Cancer Res. 65, 2804-2814. (Pubitemid 40490083)
    • (2005) Cancer Research , vol.65 , Issue.7 , pp. 2804-2814
    • Park, J.-H.1    Liu, L.2    Kim, I.-H.3    Kim, J.-H.4    You, K.-R.5    Kim, D.-G.6
  • 21
    • 18044376489 scopus 로고    scopus 로고
    • Parthenolide and sulindac cooperate to mediate growth suppression and inhibit the nuclear factor-;B pathway in pancreatic carcinoma cells
    • DOI 10.1158/1535-7163.MCT-04-0215
    • Yip-Schneider, M. T., Nakshatri, H., Sweeney, C. J., Marshall, M. S., Wiebke, E. A., and Schmidt, C. M. (2005) Parthenolide and sulindac cooperate to mediate growth suppression and inhibit the nuclear factor-κB pathway in pancreatic carcinoma cells. Mol. Cancer Ther. 4, 587-594. (Pubitemid 40601840)
    • (2005) Molecular Cancer Therapeutics , vol.4 , Issue.4 , pp. 587-594
    • Yip-Schneider, M.T.1    Nakshatri, H.2    Sweeney, C.J.3    Marshall, M.S.4    Wiebke, E.A.5    Schmidt, C.M.6
  • 23
    • 0035955729 scopus 로고    scopus 로고
    • Cysteine 38 in p65/ NF-κB plays a crucial role in DNA binding inhibition by sesquiterpene lactones
    • Garcia-Pineres, A. J., Castro, V., Mora, G., Schmidt, T. J., Strunck, E., Pahl, H. L., and Merfort, I. (2001) Cysteine 38 in p65/ NF-κB plays a crucial role in DNA binding inhibition by sesquiterpene lactones. J. Biol. Chem. 276, 39713-39720.
    • (2001) J. Biol. Chem , vol.276 , pp. 39713-39720
    • Garcia-Pineres, A.J.1    Castro, V.2    Mora, G.3    Schmidt, T.J.4    Strunck, E.5    Pahl, H.L.6    Merfort, I.7
  • 24
    • 2942618506 scopus 로고    scopus 로고
    • Role of cysteine residues of p65/NF-κB on the inhibition by the sesquiterpene lactone parthenolide and N-ethyl maleimide, and on its transactivating potential
    • DOI 10.1016/j.lfs.2004.01.024, PII S0024320504003443
    • Garcia-Pineres, A. J., Lindenmeyer, M. T., and Merfort, I. (2004) Role of cysteine residues of p65/NF-κB on the inhibition by the sesquiterpene lactone parthenolide and N-ethyl maleimide, and on its transactivating potential. Life Sci. 75, 841-856. (Pubitemid 38737421)
    • (2004) Life Sciences , vol.75 , Issue.7 , pp. 841-856
    • Garcia-Pineres, A.J.1    Lindenmeyer, M.T.2    Merfort, I.3
  • 26
    • 66449097674 scopus 로고    scopus 로고
    • Parthenolide promotes the ubiquitination of MDM2 and activates p53 cellular functions
    • Gopal, Y. N., Chanchorn, E., and Van Dyke, M. W. (2009) Parthenolide promotes the ubiquitination of MDM2 and activates p53 cellular functions. Mol Cancer Ther 8, 552-562.
    • (2009) Mol Cancer Ther , vol.8 , pp. 552-562
    • Gopal, Y.N.1    Chanchorn, E.2    Van Dyke, M.W.3
  • 27
    • 3042654962 scopus 로고    scopus 로고
    • Involvement of proapoptotic Bcl-2 family members in parthenolide-induced mitochondrial dysfunction and apoptosis
    • DOI 10.1016/j.canlet.2004.03.033, PII S0304383504002447
    • Zhang, S., Ong, C. N., and Shen, H. M. (2004) Involvement of proapoptotic Bcl-2 family members in parthenolide-induced mitochondrial dysfunction and apoptosis. Cancer Lett. 211, 175-188. (Pubitemid 38824631)
    • (2004) Cancer Letters , vol.211 , Issue.2 , pp. 175-188
    • Zhang, S.1    Ong, C.-N.2    Shen, H.-M.3
  • 29
    • 33845363571 scopus 로고    scopus 로고
    • Parthenolide-induced apoptosis in multiple myeloma cells involves reactive oxygen species generation and cell sensitivity depends on catalase activity
    • DOI 10.1007/s10495-006-0287-2
    • Wang, W., Adachi, M., Kawamura, R., Sakamoto, H., Hayashi, T., Ishida, T., Imai, K., and Shinomura, Y. (2006) Parthenolideinduced apoptosis in multiple myeloma cells involves reactive oxygen species generation and cell sensitivity depends on catalase activity. Apoptosis 11, 2225-2235. (Pubitemid 44885398)
    • (2006) Apoptosis , vol.11 , Issue.12 , pp. 2225-2235
    • Wang, W.1    Adachi, M.2    Kawamura, R.3    Sakamoto, H.4    Hayashi, T.5    Ishida, T.6    Imai, K.7    Shinomura, Y.8
  • 31
    • 34447555612 scopus 로고    scopus 로고
    • Parthenolide Specifically Depletes Histone Deacetylase 1 Protein and Induces Cell Death through Ataxia Telangiectasia Mutated
    • DOI 10.1016/j.chembiol.2007.06.007, PII S1074552107002128
    • Gopal, Y. N., Arora, T. S., and Van Dyke, M. W. (2007) Parthenolide specifically depletes histone deacetylase 1 protein and induces cell death through ataxia telangiectasia mutated. Chem. Biol. 14, 813-823. (Pubitemid 47081425)
    • (2007) Chemistry and Biology , vol.14 , Issue.7 , pp. 813-823
    • Gopal, Y.N.V.1    Arora, T.S.2    Van Dyke, M.W.3
  • 32
    • 67650311657 scopus 로고    scopus 로고
    • Aminoparthenolides as novel anti-leukemic agents: Discovery of the NF-κB inhibitor, DMAPT (LC-1)
    • Neelakantan, S., Nasim, S., Guzman, M. L., Jordan, C. T., and Crooks, P. A. (2009) Aminoparthenolides as novel anti-leukemic agents: Discovery of the NF-κB inhibitor, DMAPT (LC-1). Bioorg. Med. Chem. Lett. 19, 4346-4349.
    • (2009) Bioorg. Med. Chem. Lett , vol.19 , pp. 4346-4349
    • Neelakantan, S.1    Nasim, S.2    Guzman, M.L.3    Jordan, C.T.4    Crooks, P.A.5
  • 33
    • 47149109041 scopus 로고    scopus 로고
    • Antileukemic activity of aminoparthenolide analogs
    • Nasim, S., and Crooks, P. A. (2008) Antileukemic activity of aminoparthenolide analogs. Bioorg. Med. Chem. Lett. 18, 3870-3873.
    • (2008) Bioorg. Med. Chem. Lett , vol.18 , pp. 3870-3873
    • Nasim, S.1    Crooks, P.A.2
  • 34
    • 27744591649 scopus 로고    scopus 로고
    • Synthesis and anti-viral activity of a series of sesquiterpene lactones and analogues in the subgenomic HCV replicon system
    • DOI 10.1016/j.bmc.2005.07.055, PII S0968089605007170
    • Hwang, D. R., Chang, C. W., Lien, T. W., Chen, W. C., Tan, U. K., Hsu, J. T. A., and Hsieh, H. P. (2006) Synthesis and anti-viral activity of a series of sesquiterpene lactones and analogues in the subgenomic HCV replicon system. Bioorgan. Med. Chem. 14, 83-91. (Pubitemid 41635471)
    • (2006) Bioorganic and Medicinal Chemistry , vol.14 , Issue.1 , pp. 83-91
    • Hwang, D.-R.1    Wu, Y.-S.2    Chang, C.-W.3    Lien, T.-W.4    Chen, W.-C.5    Tan, U.-K.6    Hsu, J.T.A.7    Hsieh, H.-P.8
  • 35
    • 70249121509 scopus 로고    scopus 로고
    • Semisynthetic derivatives of sesquiterpene lactones by palladiumcatalyzed arylation of the α-methylene-lactone substructure
    • Han, C., Barrios, F. J., Riofski, M. V., and Colby, D. A. (2009) Semisynthetic derivatives of sesquiterpene lactones by palladiumcatalyzed arylation of the α-methylene-lactone substructure. J. Org. Chem. 74, 7176-7179.
    • (2009) J. Org. Chem , vol.74 , pp. 7176-7179
    • Han, C.1    Barrios, F.J.2    Riofski, M.V.3    Colby, D.A.4
  • 36
    • 81555228200 scopus 로고    scopus 로고
    • Fluorinated amino-derivatives of the sesquiterpene lactone, parthenolide, as(19)f NMR probes in deuterium-free environments
    • Woods, J. R., Mo, H., Bieberich, A. A., Alavanja, T., and Colby, D. A. (2011) Fluorinated amino-derivatives of the sesquiterpene lactone, parthenolide, as (19)f NMR probes in deuterium-free environments. J. Med. Chem. 54, 7934-7941.
    • (2011) J. Med. Chem , vol.54 , pp. 7934-7941
    • Woods, J.R.1    Mo, H.2    Bieberich, A.A.3    Alavanja, T.4    Colby, D.A.5
  • 37
    • 0034879173 scopus 로고    scopus 로고
    • The anti-inflammatory natural product parthenolide from the medicinal herb Feverfew directly binds to and inhibits IκB kinase
    • DOI 10.1016/S1074-5521(01)00049-7, PII S1074552101000497
    • Kwok, B. H., Koh, B., Ndubuisi, M. I., Elofsson, M., and Crews, C. M. (2001) The anti-inflammatory natural product parthenolide from the medicinal herb Feverfew directly binds to and inhibits IκB kinase. Chem. Biol. 8, 759-766. (Pubitemid 32752455)
    • (2001) Chemistry and Biology , vol.8 , Issue.8 , pp. 759-766
    • Kwok, B.H.B.1    Koh, B.2    Ndubuisi, M.I.3    Elofsson, M.4    Crews, C.M.5
  • 38
    • 79952588837 scopus 로고    scopus 로고
    • P450 fingerprinting method for rapid discovery of terpene hydroxylating P450 catalysts with diversified regioselectivity
    • Zhang, K., El Damaty, S., and Fasan, R. (2011) P450 fingerprinting method for rapid discovery of terpene hydroxylating P450 catalysts with diversified regioselectivity. J. Am. Chem. Soc. 133, 3242-3245.
    • (2011) J. Am. Chem. Soc , vol.133 , pp. 3242-3245
    • Zhang, K.1    El Damaty, S.2    Fasan, R.3
  • 39
    • 84869463474 scopus 로고    scopus 로고
    • Controlled oxidation of remote sp3 C-H bonds in artemisinin via P450 catalysts with fine-tuned regio-And stereoselectivity
    • Zhang, K., Shafer, B. M., Demars, M. D., 2nd, Stern, H. A., and Fasan, R. (2012) Controlled oxidation of remote sp3 C-H bonds in artemisinin via P450 catalysts with fine-tuned regio-And stereoselectivity. J. Am. Chem. Soc. 134, 18695-18704.
    • (2012) J. Am. Chem. Soc , vol.134 , pp. 18695-18704
    • Zhang, K.1    Shafer, B.M.2    Demars, M.D.3    Stern II, H.A.4    Fasan, R.5
  • 40
    • 0036842594 scopus 로고    scopus 로고
    • Laboratory evolution of a soluble, self-sufficient, highly active alkane hydroxylase
    • DOI 10.1038/nbt744
    • Glieder, A., Farinas, E. T., and Arnold, F. H. (2002) Laboratory evolution of a soluble, self-sufficient, highly active alkane hydroxylase. Nat. Biotechnol. 20, 1135-1139. (Pubitemid 35285443)
    • (2002) Nature Biotechnology , vol.20 , Issue.11 , pp. 1135-1139
    • Glieder, A.1    Farinas, E.T.2    Arnold, F.H.3
  • 41
    • 36148958632 scopus 로고    scopus 로고
    • BM3 exhibiting nativelike catalytic properties
    • DOI 10.1002/anie.200702616
    • Fasan, R., Chen, M. M., Crook, N. C., and Arnold, F. H. (2007) Engineered alkane-hydroxylating cytochrome P450(BM3) exhibiting native-like catalytic properties. Angew. Chem., Int. Ed. 46, 8414-8418. (Pubitemid 350114951)
    • (2007) Angewandte Chemie - International Edition , vol.46 , Issue.44 , pp. 8414-8418
    • Fasan, R.1    Chen, M.M.2    Crook, N.C.3    Arnold, F.H.4
  • 42
    • 57749097016 scopus 로고    scopus 로고
    • Chemoenzymatic fluorination of unactivated organic compounds
    • Rentmeister, A., Arnold, F. H., and Fasan, R. (2009) Chemoenzymatic fluorination of unactivated organic compounds. Nat. Chem. Biol. 5, 26-28.
    • (2009) Nat. Chem. Biol , vol.5 , pp. 26-28
    • Rentmeister, A.1    Arnold, F.H.2    Fasan, R.3
  • 43
    • 39549111087 scopus 로고    scopus 로고
    • BM3) variants oxidise a range of non-natural substrates and offer new selectivity options
    • DOI 10.1039/b718124h
    • Whitehouse, C. J., Bell, S. G., Tufton, H. G., Kenny, R. J., Ogilvie, L. C., and Wong, L. L. (2008) Evolved CYP102A1 (P450BM3) variants oxidize a range of non-natural substrates and offer new selectivity options. Chem. Commun., 966-968. (Pubitemid 351281049)
    • (2008) Chemical Communications , Issue.8 , pp. 966-968
    • Whitehouse, C.J.C.1    Bell, S.G.2    Tufton, H.G.3    Kenny, R.J.P.4    Ogilvie, L.C.I.5    Wong, L.-L.6
  • 45
    • 78650503853 scopus 로고    scopus 로고
    • Screening of a minimal enriched P450 BM3 mutant library for hydroxylation of cyclic and acyclic alkanes
    • Weber, E., Seifert, A., Antonovici, M., Geinitz, C., Pleiss, J., and Urlacher, V. B. (2011) Screening of a minimal enriched P450 BM3 mutant library for hydroxylation of cyclic and acyclic alkanes. Chem. Commun. 47, 944-946.
    • (2011) Chem. Commun , vol.47 , pp. 944-946
    • Weber, E.1    Seifert, A.2    Antonovici, M.3    Geinitz, C.4    Pleiss, J.5    Urlacher, V.B.6
  • 47
    • 79951893111 scopus 로고    scopus 로고
    • A regioselective biocatalyst for alkane activation under mild conditions
    • Bordeaux, M., Galarneau, A., Fajula, F., and Drone, J. (2011) A regioselective biocatalyst for alkane activation under mild conditions. Angew. Chem., Int. Ed. 50, 2075-2079.
    • (2011) Angew. Chem., Int. Ed , vol.50 , pp. 2075-2079
    • Bordeaux, M.1    Galarneau, A.2    Fajula, F.3    Drone, J.4
  • 48
    • 84856282209 scopus 로고    scopus 로고
    • Active site substitution A82W improves the regioselectivity of steroid hydroxylation by cytochrome P450 BM3 mutants as rationalized by spin relaxation nuclear magnetic resonance studies
    • Rea, V., Kolkman, A. J., Vottero, E., Stronks, E. J., Ampt, K. A., Honing, M., Vermeulen, N. P., Wijmenga, S. S., and Commandeur, J. N. (2012) Active site substitution A82W improves the regioselectivity of steroid hydroxylation by cytochrome P450 BM3 mutants as rationalized by spin relaxation nuclear magnetic resonance studies. Biochemistry 51, 750-760.
    • (2012) Biochemistry , vol.51 , pp. 750-760
    • Rea, V.1    Kolkman, A.J.2    Vottero, E.3    Stronks, E.J.4    Ampt, K.A.5    Honing, M.6    Vermeulen, N.P.7    Wijmenga, S.S.8    Commandeur, J.N.9
  • 49
    • 84859565523 scopus 로고    scopus 로고
    • Tuning P450 enzymes as oxidation catalysts
    • Fasan, R. (2012) Tuning P450 enzymes as oxidation catalysts. ACS Catal. 2, 647-666.
    • (2012) ACS Catal , vol.2 , pp. 647-666
    • Fasan, R.1
  • 50
    • 0023654954 scopus 로고
    • Identification and characterization of two functional domains in cytochrome P-450BM-3, a catalytically self-sufficient monooxygenase induced by barbiturates in Bacillus megaterium
    • Narhi, L. O., and Fulco, A. J. (1987) Identification and characterization of two functional domains in cytochrome P-450BM-3, a catalytically self-sufficient monooxygenase induced by barbiturates in Bacillus megaterium. J. Biol. Chem. 262, 6683-6690.
    • (1987) J. Biol. Chem , vol.262 , pp. 6683-6690
    • Narhi, L.O.1    Fulco, A.J.2
  • 52
    • 0029875669 scopus 로고    scopus 로고
    • Antitumor germacranolides from Anvillea garcinii
    • DOI 10.1021/np960064g
    • Abdel Sattar, E., Galal, A. M., and Mossa, G. S. (1996) Antitumor germacranolides from Anvillea garcinii. J. Nat. Prod. 59, 403-405. (Pubitemid 26139716)
    • (1996) Journal of Natural Products , vol.59 , Issue.4 , pp. 403-405
    • Sattar, E.A.1    Galal, A.M.2    Mossa, G.S.3
  • 53
    • 0033026016 scopus 로고    scopus 로고
    • Microbial transformation of parthenolide
    • DOI 10.1016/S0031-9422(99)00066-7, PII S0031942299000667
    • Galal, A. M., Ibrahim, A. R. S., Mossa, J. S., and El-Feraly, F. S. (1999) Microbial transformation of parthenolide. Phytochemistry 51, 761-765. (Pubitemid 29289196)
    • (1999) Phytochemistry , vol.51 , Issue.6 , pp. 761-765
    • Galal, A.M.1    Ibrahim, A.-R.S.2    Mossa, J.S.3    El-Feraly, F.S.4
  • 56
    • 0036708522 scopus 로고    scopus 로고
    • The maximum common substructure as a molecular depiction in a supervised classification context: Experiments in quantitative structure/biodegradability relationships
    • DOI 10.1021/ci020017w
    • Cuissart, B., Touffet, F., Cremilleux, B., Bureau, R., and Rault, S. (2002) The maximum common substructure as a molecular depiction in a supervised classification context: Experiments in quantitative structure/biodegradability relationships. J. Chem. Inf. Comput. Sci. 42, 1043-1052. (Pubitemid 35360287)
    • (2002) Journal of Chemical Information and Computer Sciences , vol.42 , Issue.5 , pp. 1043-1052
    • Cuissart, B.1    Touffet, F.2    Cremilleux, B.3    Bureau, R.4    Rault, S.5
  • 57
    • 46249123633 scopus 로고    scopus 로고
    • A maximum common substructure-based algorithm for searching and predicting drug-like compounds
    • Cao, Y., Jiang, T., and Girke, T. (2008) A maximum common substructure-based algorithm for searching and predicting drug-like compounds. Bioinformatics 24, 366-374.
    • (2008) Bioinformatics , vol.24 , pp. 366-374
    • Cao, Y.1    Jiang, T.2    Girke, T.3
  • 60
    • 0031033653 scopus 로고    scopus 로고
    • A single mutation in cytochrome P450 BM3 changes substrate orientation in a catalytic intermediate and the regiospecificity of hydroxylation
    • DOI 10.1021/bi962826c
    • Oliver, C. F., Modi, S., Sutcliffe, M. J., Primrose, W. U., Lian, L. Y., and Roberts, G. C. (1997) A single mutation in cytochrome P450 BM3 changes substrate orientation in a catalytic intermediate and the regiospecificity of hydroxylation. Biochemistry 36, 1567-1572. (Pubitemid 27086252)
    • (1997) Biochemistry , vol.36 , Issue.7 , pp. 1567-1572
    • Oliver, C.F.1    Modi, S.2    Sutcliffe, M.J.3    Primrose, W.U.4    Lian, L.-Y.5    Roberts, G.C.K.6
  • 61
    • 38449096799 scopus 로고    scopus 로고
    • Further improvement of phosphite dehydrogenase thermostability by saturation mutagenesis
    • DOI 10.1002/bit.21546
    • McLachlan, M. J., Johannes, T. W., and Zhao, H. (2008) Further improvement of phosphite dehydrogenase thermostability by saturation mutagenesis. Biotechnol. Bioeng. 99, 268-274. (Pubitemid 351158275)
    • (2008) Biotechnology and Bioengineering , vol.99 , Issue.2 , pp. 268-274
    • McLachlan, M.J.1    Johannes, T.W.2    Zhao, H.3
  • 63
    • 37049096251 scopus 로고
    • Crystal and molecularstructure of parthenolide [4,5-epoxygermacra-1(10), 11(13)-dien-12,6-olactone]
    • Quick, A., and Rogers, D. (1976) Crystal and molecularstructure of parthenolide [4,5-epoxygermacra-1(10),11(13)-dien-12,6-olactone]. J. Chem. Soc., Perkin Trans. 2, 465-469.
    • (1976) J. Chem. Soc., Perkin Trans , vol.2 , pp. 465-469
    • Quick, A.1    Rogers, D.2


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