蛋白酶体抑制剂Syrbactins家族的生物合成
|
摘要
微生物来源的syrbactins属于十二元内酰胺短肽类化合物,包括丁香霉素(syringolins)、滑杆菌素(glidobactins)、cepafungins和luminmycins等。其中,syringolins、glidobactins、luminmycins等几个化合物生物合成基因簇已被克隆、测序和异源表达。研究发现它们的十二元内酰胺环骨架都是由非核糖体肽合成酶(NRPS)-聚酮合酶(PKS)复合体采用模块化组装的方式,将系列底物组装而成。这类化合物因具有优异的蛋白酶体抑制活性而受到广泛关注。本文从syrbactins的分子结构、生物合成、作用机理等几个方面进行综述,介绍了近年来syrbactins的研究进展。
Syrbactins are microbial natural products, mainly composed of syringolins, glidobactins, cepafunins and luminmycins. At present, several biosynthetic gene clusters of syringolins and other compounds have been cloned,sequenced and heterologously expressed. These studies revealed that, despite the structural differences between syrbactins, they are synthesized in vivo in a similar mode and share a NRPS-PKS hybrid assembly biosynthetic pathway for the formation of their core skeletons. They have drawn continuous research attentions due to the irreversible proteasome inhibition activity. This review focuses on the research advances in syrbactins and highlights their structure, biosynthesis and mode-of-action.
Syrbactins are microbial natural products, mainly composed of syringolins, glidobactins, cepafunins and luminmycins. At present, several biosynthetic gene clusters of syringolins and other compounds have been cloned,sequenced and heterologously expressed. These studies revealed that, despite the structural differences between syrbactins, they are synthesized in vivo in a similar mode and share a NRPS-PKS hybrid assembly biosynthetic pathway for the formation of their core skeletons. They have drawn continuous research attentions due to the irreversible proteasome inhibition activity. This review focuses on the research advances in syrbactins and highlights their structure, biosynthesis and mode-of-action.
引文
[1]Oka M,Yaginuma K,Numata K,Konishi M,Oki T,Kawaguchi H.Glidobactins A,B and C,new antitumor antibiotics.II.Structure elucidation.The Journal of Antibiotics,1988,41(10):1338-1350.
[2]Oka M,Ohkuma H,Kamei H,Konishi M,Oki T,Kawaguchi H.Glidobactins D,E,F,G and H;minor components of the antitumor antibiotic glidobactin.The Journal of Antibiotics,1988,41(12):1906-1909.
[3]W?spi U,Blanc D,Winkler T,Rüedi P,Dudler R.Syringolin,a novel peptide elicitor from Pseudomonas syringae pv.syringae that induces resistance to Pyricularia oryzae in rice.Molecular Plant-Microbe Interactions,1998,11(8):727-733.
[4]W?spi U,Hassa P,Staempfli AA,Molleyres LP,Winkler T,Dudler R.Identification and structure of a family of syringolin variants:Unusual cyclic peptides from Pseudomonas syringae pv.syringae that elicit defense responses in rice.Microbiological Research,1999,154(1):89-93.
[5]Bian XY,Huang F,Stewart FA,Xia LQ,Zhang YM,Müller R.Direct cloning,genetic engineering,and heterologous expression of the syringolin biosynthetic gene cluster in E.coli through Red/ET recombineering.ChemBioChem,2012,13(13):1946-1952.
[6]Shoji J,Hinoo H,Kato T,Hattori T,Hirooka K,Tawara K,Shiratori O,Terui Y.Isolation of cepafungins I,II and IIIfrom Pseudomonas species.The Journal of Antibiotics,1990,43(7):783-787.
[7]Terui Y,Nishikawa J,Hinoo H,Kato T,Shoji J.Structures of cepafungins I,II and III.The Journal of Antibiotics,1990,43(7):788-795.
[8]Bian XY,Plaza A,Zhang YM,Müller R.Luminmycins A-C,cryptic natural products from Photorhabdus luminescens identified by heterologous expression in Escherichia coli.Journal of Natural Products,2012,75(9):1652-1655.
[9]Theodore CM,King JB,You JL,Cichewicz RH.Production of cytotoxic glidobactins/luminmycins by Photorhabdus asymbiotica in liquid media and live crickets.Journal of Natural Products,2012,75(11):2007-2011.
[10]Amrein H,Makart S,Granado J,Shakya R,Schneider-Pokorny J,Dudler R.Functional analysis of genes involved in the synthesis of Syringolin A by Pseudomonas syringae pv.syringae B301D-R.Molecular Plant-Microbe Interactions,2004,17(1):90-97.
[11]Walsh CT.Polyketide and nonribosomal peptide antibiotics:modularity and versatility.Science,2004,303(5665):1805-1810.
[12]Schellenberg B,Bigler L,Dudler R.Identification of genes involved in the biosynthesis of the cytotoxic compound glidobactin from a soil bacterium.Environmental Microbiology,2007,9(7):1640-1650.
[13]Biggins JB,Kang HS,Ternei MA,DeShazer D,Brady SF.The chemical arsenal of Burkholderia pseudomallei is essential for pathogenicity.Journal of the American Chemical Society,2014,136(26):9484-9490.
[14]Ramel C,Tobler M,Meyer M,Bigler L,Ebert MO,Schellenberg B,Dudler R.Biosynthesis of the proteasome inhibitor Syringolin A:the ureido group joining two amino acids originates from bicarbonate.BMC Biochemistry,2009,10:26.
[15]Imker HJ,Walsh CT,Wuest WM.SylC catalyzes ureido-bond formation during biosynthesis of the proteasome inhibitor Syringolin A.Journal of the American Chemical Society,2009,131(51):18263-18265.
[16]Imker HJ,Krahn D,Clerc J,Kaiser M,Walsh CT.N-Acylation during glidobactin biosynthesis by the tridomain nonribosomal peptide synthetase module GlbF.Chemistry&Biology,2010,17(10):1077-1083.
[17]Borissenko L,Groll M.20S proteasome and its inhibitors:crystallographic knowledge for drug development.Chemical Reviews,2007,107(3):687-717.
[18]Pearce MJ,Mintseris J,Ferreyra J,Gygi SP,Darwin KH.Ubiquitin-like protein involved in the proteasome pathway of Mycobacterium tuberculosis.Science,2008,322(5904):1104-1107.
[19]Hu GQ,Lin G,Wang M,Dick L,Xu RM,Nathan C,Li HL.Structure of the Mycobacterium tuberculosis proteasome and mechanism of inhibition by a peptidyl boronate.Molecular Microbiology,2006,59(5):1417-1428.
[20]Groll M,Schellenberg B,Bachmann AS,Archer CR,Huber R,Powell TK,Lindow S,Kaiser M,Dudler R.A plant pathogen virulence factor inhibits the eukaryotic proteasome by a novel mechanism.Nature,2008,452(7188):755-758.
[21]Chen L,Madura K.Increased proteasome activity,ubiquitin-conjugating enzymes,and eEF1A translation factor detected in breast cancer tissue.Cancer Research,2005,65(13):5599-5606.
[22]?led?P,Baumeister W.Structure-driven developments of26S proteasome inhibitors.Annual Review of Pharmacology and Toxicology,2016,56(1):191-209.
[23]Rentsch A,Landsberg D,Brodmann T,Bülow Leila,Girbig AK,Kalesse M.Synthesis and pharmacology of proteasome inhibitors.Angewandte Chemie International Edition,2013,52(21):5450-5488.
[24]Coleman CS,Rocetes JP,Park DJ,Wallick CJ,Warn-Cramer BJ,Michel K,Dudler R,Bachmann AS.Syringolin A,a new plant elicitor from the phytopathogenic bacterium Pseudomonas syringae pv.syringae,inhibits the proliferation of neuroblastoma and ovarian cancer cells and induces apoptosis.Cell Proliferation,2006,39(6):599-609.
[25]Oka M,Numata K,Nishiyama Y,Kamei H,Konishi M,Oki T,Kawaguchi H.Chemical modification of the antitumor antibiotic glidobactin.The Journal of Antibiotics,1988,41(12):1812-1822.
[26]Archer CR,Koomoa DLT,Mitsunaga EM,Clerc J,Shimizu M,Kaiser M,Schellenberg B,Dudler R,Bachmann AS.Syrbactin class proteasome inhibitor-induced apoptosis and autophagy occurs in association with p53 accumulation and Akt/PKB activation in neuroblastoma.Biochemical Pharmacology,2010,80(2):170-178.
[27]Stein ML,Beck P,Kaiser M,Dudler R,Becker CFW,Groll M.One-shot NMR analysis of microbial secretions identifies highly potent proteasome inhibitor.Proceedings of the National Academy of Sciences of the United States of America,2012,109(45):18367-18371.
[28]Totaro KA,Barthelme D,Simpson PT,Jiang XJ,Lin G,Nathan CF,Sauer RT,Sello JK.Rational design of selective and bioactive inhibitors of the Mycobacterium tuberculosis proteasome.ACS Infectious Diseases,2017,3(2):176-181.
[29]Clerc J,Groll M,Illich DJ,Bachmann AS,Huber R,Schellenberg B,Dudler R,Kaiser M.Synthetic and structural studies on Syringolin A and B reveal critical determinants of selectivity and potency of proteasome inhibition.Proceedings of the National Academy of Sciences of the United States of America,2009,106(16):6507-6512.
[30]Clerc J,Schellenberg B,Groll M,Bachmann AS,Huber R,Dudler R,Kaiser M.Convergent synthesis and biological evaluation of Syringolin A and derivatives as eukaryotic 20Sproteasome inhibitors.European Journal of Organic Chemistry,2010,2010(21):3991-4003.
[31]Clerc J,Li N,Krahn D,Groll M,Bachmann AS,Florea BI,Overkleeft HS,Kaiser M.The natural product hybrid of Syringolin A and Glidobactin A synergizes proteasome inhibition potency with subsite selectivity.Chemical Communications,2011,47(1):385-387.
[32]Chiba T,Hosono H,Nakagawa K,Asaka M,Takeda H,Matsuda A,Ichikawa S.Total synthesis of Syringolin A and improvement of its biological activity.Angewandte Chemie International Edition,2014,53(19):4836-4839.
[33]Kolodziejek I,Misas-Villamil JC,Kaschani F,Clerc J,Gu C,Krahn D,Niessen S,Verdoes M,Willems LI,Overkleeft HS,Kaiser M,van der Hoorn RAL.Proteasome activity imaging and profiling characterizes bacterial effector Syringolin A.Plant Physiology,2011,155(1):477-489.
[34]Bachmann AS,Opoku-Ansah J,Ibarra-Rivera TR,Yco LP,Ambadi S,Roberts CC,Chang CA,Pirrung MC.Syrbactin structural analog TIR-199 blocks proteasome activity and induces tumor cell death.Journal of Biological Chemistry,2016,291(16):8350-8362.
[35]Bakas NA,Schultz CR,Yco LP,Roberts CC,Chang CA,Bachmann AS,Pirrung MC.Immunoproteasome inhibition and bioactivity of thiasyrbactins.Bioorganic&Medicinal Chemistry,2018,26(2):401-412.
[36]Yoshida T,Ri M,Kanamori T,Aoki S,Ashour R,Kinoshita S,Narita T,Totani H,Masaki A,Ito A,Kusumoto S,Ishida T,Komatsu H,Kitahata S,Chiba T,Ichikawa S,Iida S.Potent anti-tumor activity of a syringolin analog in multiple myeloma:a dual inhibitor of proteasome activity targetingβ2 andβ5 subunits.Oncotarget,2018,9(11):9975-9991.
[37]Fu J,Bian XY,Hu SB,Wang HL,Huang F,Seibert PM,Plaza A,Xia LQ,Müller R,Stewart AF,Zhang YM.Full-length RecE enhances linear-linear homologous recombination and facilitates direct cloning for bioprospecting.Nature Biotechnology,2012,30(5):440-446.
[38]Wang HL,Li Z,Jia RN,Yin J,Li AY,Xia LQ,Yin YL,Müller R,Fu J,Stewart AF,Zhang YM.ExoCET:exonuclease in vitro assembly combined with RecETrecombination for highly efficient direct DNA cloning from complex genomes.Nucleic Acids Research,2018,46(5):e28.
[39]Wang HL,Li Z,Jia RN,Hou Y,Yin J,Bian XY,Li AY,Müller R,Stewart AF,Fu J,Zhang YM.RecET direct cloning and Redαβrecombineering of biosynthetic gene clusters,large operons or single genes for heterologous expression.Nature Protocols,2016,11(7):1175-1190.
[40]Bian XY,Huang F,Wang HL,Klefisch T,Müller R,Zhang YM.Heterologous Production of glidobactins/luminmycins in Escherichia coli Nissle containing the glidobactin biosynthetic gene cluster from Burkholderia DSM7029.ChemBioChem,2014,15(15):2221-2224.
[41]Huang F,Tang JL,He L,Ding XZ,Huang SY,Zhang YM,Sun YJ,Xia LQ.Heterologous expression and antitumor activity analysis of syringolin from Pseudomonas syringae pv.syringae B728a.Microbial Cell Factories,2018,17:31.
[42]Wang X,Zhou HB,Chen HN,Jing XS,Zheng WT,Li RJ,Sun T,Liu JQ,Fu J,Huo LJ,Li YZ,Shen YM,Ding XM,Müller R,Bian XY,Zhang YM.Discovery of recombinases enables genome mining of cryptic biosynthetic gene clusters in Burkholderiales species.Proceedings of the National Academy of Sciences of the United States of America,2018,115(18):E4255-E4263.
[43]Price CTD,Al-Quadan T,Santic M,Rosenshine I,Kwaik YA.Host proteasomal degradation generates amino acids essential for intracellular bacterial growth.Science,2011,334(6062):1553-1557.
[44]Kane RC,Bross PF,Farrell AT,Pazdur R.Velcade?:U.S.FDA approval for the treatment of multiple myeloma progressing on prior therapy.Oncologist,2003,8(6):508-513.
[45]Murray MY,Auger MJ,Bowles KM.Overcoming bortezomib resistance in multiple myeloma.Biochemical Society Transactions,2014,42(4):804-808.
[46]Dimopoulos MA,Goldschmidt H,Niesvizky R,Joshua D,Chng WJ,Oriol A,Orlowski RZ,Ludwig H,Facon T,Hajek R,Weisel K,Hungria V,Minuk L,Feng SB,Zahlten-Kumeli A,Kimball AS,Moreau P.Carfilzomib or bortezomib in relapsed or refractory multiple myeloma(ENDEAVOR):an interim overall survival analysis of an open-label,randomised,phase 3 trial.The Lancet Oncology,2017,18(10):1327-1337.
[47]Feling RH,Buchanan GO,Mincer TJ,Kauffman CA,Jensen PR,Fenical W.Salinosporamide A:A highly cytotoxic proteasome inhibitor from a novel microbial source,a marine bacterium of the new genus Salinospora.Angewandte Chemie International Edition,2003,42(3):355-357.
[48]Krahn D,Ottmann C,Kaiser M.The chemistry and biology of syringolins,glidobactins and cepafungins(syrbactins).Natural Product Reports,2011,28(11):1854-1867.
[2]Oka M,Ohkuma H,Kamei H,Konishi M,Oki T,Kawaguchi H.Glidobactins D,E,F,G and H;minor components of the antitumor antibiotic glidobactin.The Journal of Antibiotics,1988,41(12):1906-1909.
[3]W?spi U,Blanc D,Winkler T,Rüedi P,Dudler R.Syringolin,a novel peptide elicitor from Pseudomonas syringae pv.syringae that induces resistance to Pyricularia oryzae in rice.Molecular Plant-Microbe Interactions,1998,11(8):727-733.
[4]W?spi U,Hassa P,Staempfli AA,Molleyres LP,Winkler T,Dudler R.Identification and structure of a family of syringolin variants:Unusual cyclic peptides from Pseudomonas syringae pv.syringae that elicit defense responses in rice.Microbiological Research,1999,154(1):89-93.
[5]Bian XY,Huang F,Stewart FA,Xia LQ,Zhang YM,Müller R.Direct cloning,genetic engineering,and heterologous expression of the syringolin biosynthetic gene cluster in E.coli through Red/ET recombineering.ChemBioChem,2012,13(13):1946-1952.
[6]Shoji J,Hinoo H,Kato T,Hattori T,Hirooka K,Tawara K,Shiratori O,Terui Y.Isolation of cepafungins I,II and IIIfrom Pseudomonas species.The Journal of Antibiotics,1990,43(7):783-787.
[7]Terui Y,Nishikawa J,Hinoo H,Kato T,Shoji J.Structures of cepafungins I,II and III.The Journal of Antibiotics,1990,43(7):788-795.
[8]Bian XY,Plaza A,Zhang YM,Müller R.Luminmycins A-C,cryptic natural products from Photorhabdus luminescens identified by heterologous expression in Escherichia coli.Journal of Natural Products,2012,75(9):1652-1655.
[9]Theodore CM,King JB,You JL,Cichewicz RH.Production of cytotoxic glidobactins/luminmycins by Photorhabdus asymbiotica in liquid media and live crickets.Journal of Natural Products,2012,75(11):2007-2011.
[10]Amrein H,Makart S,Granado J,Shakya R,Schneider-Pokorny J,Dudler R.Functional analysis of genes involved in the synthesis of Syringolin A by Pseudomonas syringae pv.syringae B301D-R.Molecular Plant-Microbe Interactions,2004,17(1):90-97.
[11]Walsh CT.Polyketide and nonribosomal peptide antibiotics:modularity and versatility.Science,2004,303(5665):1805-1810.
[12]Schellenberg B,Bigler L,Dudler R.Identification of genes involved in the biosynthesis of the cytotoxic compound glidobactin from a soil bacterium.Environmental Microbiology,2007,9(7):1640-1650.
[13]Biggins JB,Kang HS,Ternei MA,DeShazer D,Brady SF.The chemical arsenal of Burkholderia pseudomallei is essential for pathogenicity.Journal of the American Chemical Society,2014,136(26):9484-9490.
[14]Ramel C,Tobler M,Meyer M,Bigler L,Ebert MO,Schellenberg B,Dudler R.Biosynthesis of the proteasome inhibitor Syringolin A:the ureido group joining two amino acids originates from bicarbonate.BMC Biochemistry,2009,10:26.
[15]Imker HJ,Walsh CT,Wuest WM.SylC catalyzes ureido-bond formation during biosynthesis of the proteasome inhibitor Syringolin A.Journal of the American Chemical Society,2009,131(51):18263-18265.
[16]Imker HJ,Krahn D,Clerc J,Kaiser M,Walsh CT.N-Acylation during glidobactin biosynthesis by the tridomain nonribosomal peptide synthetase module GlbF.Chemistry&Biology,2010,17(10):1077-1083.
[17]Borissenko L,Groll M.20S proteasome and its inhibitors:crystallographic knowledge for drug development.Chemical Reviews,2007,107(3):687-717.
[18]Pearce MJ,Mintseris J,Ferreyra J,Gygi SP,Darwin KH.Ubiquitin-like protein involved in the proteasome pathway of Mycobacterium tuberculosis.Science,2008,322(5904):1104-1107.
[19]Hu GQ,Lin G,Wang M,Dick L,Xu RM,Nathan C,Li HL.Structure of the Mycobacterium tuberculosis proteasome and mechanism of inhibition by a peptidyl boronate.Molecular Microbiology,2006,59(5):1417-1428.
[20]Groll M,Schellenberg B,Bachmann AS,Archer CR,Huber R,Powell TK,Lindow S,Kaiser M,Dudler R.A plant pathogen virulence factor inhibits the eukaryotic proteasome by a novel mechanism.Nature,2008,452(7188):755-758.
[21]Chen L,Madura K.Increased proteasome activity,ubiquitin-conjugating enzymes,and eEF1A translation factor detected in breast cancer tissue.Cancer Research,2005,65(13):5599-5606.
[22]?led?P,Baumeister W.Structure-driven developments of26S proteasome inhibitors.Annual Review of Pharmacology and Toxicology,2016,56(1):191-209.
[23]Rentsch A,Landsberg D,Brodmann T,Bülow Leila,Girbig AK,Kalesse M.Synthesis and pharmacology of proteasome inhibitors.Angewandte Chemie International Edition,2013,52(21):5450-5488.
[24]Coleman CS,Rocetes JP,Park DJ,Wallick CJ,Warn-Cramer BJ,Michel K,Dudler R,Bachmann AS.Syringolin A,a new plant elicitor from the phytopathogenic bacterium Pseudomonas syringae pv.syringae,inhibits the proliferation of neuroblastoma and ovarian cancer cells and induces apoptosis.Cell Proliferation,2006,39(6):599-609.
[25]Oka M,Numata K,Nishiyama Y,Kamei H,Konishi M,Oki T,Kawaguchi H.Chemical modification of the antitumor antibiotic glidobactin.The Journal of Antibiotics,1988,41(12):1812-1822.
[26]Archer CR,Koomoa DLT,Mitsunaga EM,Clerc J,Shimizu M,Kaiser M,Schellenberg B,Dudler R,Bachmann AS.Syrbactin class proteasome inhibitor-induced apoptosis and autophagy occurs in association with p53 accumulation and Akt/PKB activation in neuroblastoma.Biochemical Pharmacology,2010,80(2):170-178.
[27]Stein ML,Beck P,Kaiser M,Dudler R,Becker CFW,Groll M.One-shot NMR analysis of microbial secretions identifies highly potent proteasome inhibitor.Proceedings of the National Academy of Sciences of the United States of America,2012,109(45):18367-18371.
[28]Totaro KA,Barthelme D,Simpson PT,Jiang XJ,Lin G,Nathan CF,Sauer RT,Sello JK.Rational design of selective and bioactive inhibitors of the Mycobacterium tuberculosis proteasome.ACS Infectious Diseases,2017,3(2):176-181.
[29]Clerc J,Groll M,Illich DJ,Bachmann AS,Huber R,Schellenberg B,Dudler R,Kaiser M.Synthetic and structural studies on Syringolin A and B reveal critical determinants of selectivity and potency of proteasome inhibition.Proceedings of the National Academy of Sciences of the United States of America,2009,106(16):6507-6512.
[30]Clerc J,Schellenberg B,Groll M,Bachmann AS,Huber R,Dudler R,Kaiser M.Convergent synthesis and biological evaluation of Syringolin A and derivatives as eukaryotic 20Sproteasome inhibitors.European Journal of Organic Chemistry,2010,2010(21):3991-4003.
[31]Clerc J,Li N,Krahn D,Groll M,Bachmann AS,Florea BI,Overkleeft HS,Kaiser M.The natural product hybrid of Syringolin A and Glidobactin A synergizes proteasome inhibition potency with subsite selectivity.Chemical Communications,2011,47(1):385-387.
[32]Chiba T,Hosono H,Nakagawa K,Asaka M,Takeda H,Matsuda A,Ichikawa S.Total synthesis of Syringolin A and improvement of its biological activity.Angewandte Chemie International Edition,2014,53(19):4836-4839.
[33]Kolodziejek I,Misas-Villamil JC,Kaschani F,Clerc J,Gu C,Krahn D,Niessen S,Verdoes M,Willems LI,Overkleeft HS,Kaiser M,van der Hoorn RAL.Proteasome activity imaging and profiling characterizes bacterial effector Syringolin A.Plant Physiology,2011,155(1):477-489.
[34]Bachmann AS,Opoku-Ansah J,Ibarra-Rivera TR,Yco LP,Ambadi S,Roberts CC,Chang CA,Pirrung MC.Syrbactin structural analog TIR-199 blocks proteasome activity and induces tumor cell death.Journal of Biological Chemistry,2016,291(16):8350-8362.
[35]Bakas NA,Schultz CR,Yco LP,Roberts CC,Chang CA,Bachmann AS,Pirrung MC.Immunoproteasome inhibition and bioactivity of thiasyrbactins.Bioorganic&Medicinal Chemistry,2018,26(2):401-412.
[36]Yoshida T,Ri M,Kanamori T,Aoki S,Ashour R,Kinoshita S,Narita T,Totani H,Masaki A,Ito A,Kusumoto S,Ishida T,Komatsu H,Kitahata S,Chiba T,Ichikawa S,Iida S.Potent anti-tumor activity of a syringolin analog in multiple myeloma:a dual inhibitor of proteasome activity targetingβ2 andβ5 subunits.Oncotarget,2018,9(11):9975-9991.
[37]Fu J,Bian XY,Hu SB,Wang HL,Huang F,Seibert PM,Plaza A,Xia LQ,Müller R,Stewart AF,Zhang YM.Full-length RecE enhances linear-linear homologous recombination and facilitates direct cloning for bioprospecting.Nature Biotechnology,2012,30(5):440-446.
[38]Wang HL,Li Z,Jia RN,Yin J,Li AY,Xia LQ,Yin YL,Müller R,Fu J,Stewart AF,Zhang YM.ExoCET:exonuclease in vitro assembly combined with RecETrecombination for highly efficient direct DNA cloning from complex genomes.Nucleic Acids Research,2018,46(5):e28.
[39]Wang HL,Li Z,Jia RN,Hou Y,Yin J,Bian XY,Li AY,Müller R,Stewart AF,Fu J,Zhang YM.RecET direct cloning and Redαβrecombineering of biosynthetic gene clusters,large operons or single genes for heterologous expression.Nature Protocols,2016,11(7):1175-1190.
[40]Bian XY,Huang F,Wang HL,Klefisch T,Müller R,Zhang YM.Heterologous Production of glidobactins/luminmycins in Escherichia coli Nissle containing the glidobactin biosynthetic gene cluster from Burkholderia DSM7029.ChemBioChem,2014,15(15):2221-2224.
[41]Huang F,Tang JL,He L,Ding XZ,Huang SY,Zhang YM,Sun YJ,Xia LQ.Heterologous expression and antitumor activity analysis of syringolin from Pseudomonas syringae pv.syringae B728a.Microbial Cell Factories,2018,17:31.
[42]Wang X,Zhou HB,Chen HN,Jing XS,Zheng WT,Li RJ,Sun T,Liu JQ,Fu J,Huo LJ,Li YZ,Shen YM,Ding XM,Müller R,Bian XY,Zhang YM.Discovery of recombinases enables genome mining of cryptic biosynthetic gene clusters in Burkholderiales species.Proceedings of the National Academy of Sciences of the United States of America,2018,115(18):E4255-E4263.
[43]Price CTD,Al-Quadan T,Santic M,Rosenshine I,Kwaik YA.Host proteasomal degradation generates amino acids essential for intracellular bacterial growth.Science,2011,334(6062):1553-1557.
[44]Kane RC,Bross PF,Farrell AT,Pazdur R.Velcade?:U.S.FDA approval for the treatment of multiple myeloma progressing on prior therapy.Oncologist,2003,8(6):508-513.
[45]Murray MY,Auger MJ,Bowles KM.Overcoming bortezomib resistance in multiple myeloma.Biochemical Society Transactions,2014,42(4):804-808.
[46]Dimopoulos MA,Goldschmidt H,Niesvizky R,Joshua D,Chng WJ,Oriol A,Orlowski RZ,Ludwig H,Facon T,Hajek R,Weisel K,Hungria V,Minuk L,Feng SB,Zahlten-Kumeli A,Kimball AS,Moreau P.Carfilzomib or bortezomib in relapsed or refractory multiple myeloma(ENDEAVOR):an interim overall survival analysis of an open-label,randomised,phase 3 trial.The Lancet Oncology,2017,18(10):1327-1337.
[47]Feling RH,Buchanan GO,Mincer TJ,Kauffman CA,Jensen PR,Fenical W.Salinosporamide A:A highly cytotoxic proteasome inhibitor from a novel microbial source,a marine bacterium of the new genus Salinospora.Angewandte Chemie International Edition,2003,42(3):355-357.
[48]Krahn D,Ottmann C,Kaiser M.The chemistry and biology of syringolins,glidobactins and cepafungins(syrbactins).Natural Product Reports,2011,28(11):1854-1867.