抗菌环肽的研究进展
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摘要
鉴于禽类细菌性疾病对养禽业健康发展的不利影响,人们急需开发改善细菌耐药性的新型敏感性抗菌药物,使其达到治疗细菌性疾病的目的。环肽较线性肽因具有更多的生物活性和医药价值而成为抗菌药物的候选者。主要从天然抗菌环肽的发现、抗菌环肽的合成、环肽类抗菌药物的应用现状三个方面进行综述,期望有利于读者进一步了解抗菌环肽的研究概况,为开发新型抗菌环肽药物提供帮助。
In view of the adverse effects of avian bacterial diseases on the healthy development of the poultry industry,there is an urgent need to develop new sensitive antimicrobial agents that improve bacterial resistance so as to achieve the purpose of treating bacterial diseases. Cyclic peptides are candidates for antibacterials because they have more biological activities and medicinal properties than linear peptides. The discovery of natural antibacterial cyclic peptides,the synthesis of antibacterial cyclic peptides and the application status of antibacterial cyclic peptide drugs were mainly reviewed. It is expected to help readers to further understand the research situation of antibacterial cyclic peptides and provide assistance for the development of new antibacterial cyclic peptide drugs.
In view of the adverse effects of avian bacterial diseases on the healthy development of the poultry industry,there is an urgent need to develop new sensitive antimicrobial agents that improve bacterial resistance so as to achieve the purpose of treating bacterial diseases. Cyclic peptides are candidates for antibacterials because they have more biological activities and medicinal properties than linear peptides. The discovery of natural antibacterial cyclic peptides,the synthesis of antibacterial cyclic peptides and the application status of antibacterial cyclic peptide drugs were mainly reviewed. It is expected to help readers to further understand the research situation of antibacterial cyclic peptides and provide assistance for the development of new antibacterial cyclic peptide drugs.
引文
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[3]Mor-Mur M,Yuste J. Emerging bacterial pathogens in meat and poultry:An Overview. Food and Bioprocess Technology,2009,3(1):24-35.
[4]Jennings J L,Sait L C,Perrett C A,et al. Campylobacter jejuni is associated with,but not sufficient to cause vibrionic hepatitis in chickens. Vet Microbiol,2011,149(1-2):193-199.
[5] Chaves Hernández A J. Poultry and avian diseases. In:Encyclopedia of agriculture and food systems. Oxford:Academic Press,2014:504-520.
[6]Hoon J S. Cyclic Peptides as therapeutic agents and biochemical tools. Biomolecules&Therapeutics,2012,20(1):19-26.
[7] Borthwick A D. 2,5-Diketopiperazines:synthesis,reactions,medicinal chemistry, and bioactive natural products.Cheminform,2012,112(7):3641-3716.
[8]Listed N. Discovery and applications of naturally occurring cyclic peptides. Drug Discovery Today Technologies,2012,9(1):1-70.
[9]Gause G F,Brazhnikova M G. Gramicidin S and its use in the treatment of infected wounds. Nature,1944,154(3918):703.
[10]Ovchinnikov Y A, Ivanov V T. ChemInform abstract:conformational states and biological activity of cyclic peptides.Tetrahedron,1975,31(18):2177-2209.
[11]Conti E,Stachelhaus T,Marahiel M A,et al. Structural basis for the activation of phenylalanine in the non-ribosomal biosynthesis of gramicidin S. Embo Journal,1997,16(14):4174-4183.
[12] Velkov T,Roberts K D,Nation R L,et al. Pharmacology of polymyxins:new insights into an'old'class of antibiotics. Future Microbiology,2013,8(6):711-724.
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[15]Nicolaou K C,Boddy C N,Brse S,et al. Chemistry,Biology,and Medicine of the Glycopeptide Antibiotics. Angewandte Chemie,1999,30(45):2096-2152.
[16] Liskamp R M J,Rijkers D T S,Bakker S E. Bioactive macrocyclic peptides and peptide mimics. Modern Supramolecular Chemistry:Strategies for Macrocycle Synthesis,2008,1-27.
[17] Armando G R, Andrew S R, Kamal H. Daptomycin:an evidence-based review of its role in the treatment of Gram-positive infections. Infection&Drug Resistance,2016,9(1):47-58.
[18]Kaya S,Yilmaz G,Kalkan A,et al. Treatment of gram-positive left-sided infective endocarditis with daptomycin. Journal of Infection&Chemotherapy,2013,19(4):698-702.
[19] Xing Y,Wang W,Dai S,et al. Daptomycin exerts rapid bactericidal activity against Bacillus anthracis without disrupting membrane integrity. Acta Pharmacologica Sinica,2014,35(2):211-218.
[20] Pogliano J,Pogliano N,Silverman J A. Daptomycin-mediated reorganization of membrane architecture causes mislocalization of essential cell division proteins. Journal of Bacteriology,2012,194(17):4494-4504.
[21] Huang E,Guo Y,Yousef A E. Draft genome sequence of Paenibacillus sp. strain OSY-SE,a bacterium producing the novel broad-spectrum lipopeptide antibiotic paenibacterin. Journal of Bacteriology,2012,194(22):6306.
[22] Huang E,Guo Y,Yousef A E. Biosynthesis of the new broadspectrum lipopeptide antibiotic paenibacterin in Paenibacillus thiaminolyticus OSY-SE. Research in Microbiology,2014,165(3):243-251.
[23] Qin C,Xu C,Zhang R,et al. On-resin cyclization and antimicrobial activity of Laterocidin and its analogues.Tetrahedron Letters,2010,51(9):1257-1261.
[24]Kaweewan I,Hemmi H,Komaki H,et al. Isolation and structure determination of new antibacterial peptide curacomycin based on genome mining. Asian Journal of Organic Chemistry,2017,6(12):1838-1844.
[25]Gong A D,Li H P,Yuan Q S,et al. Antagonistic mechanism of iturin A and plipastatin A from Bacillus amyloliquefaciens S76-3from wheat spikes against Fusarium graminearum. PLo S One,2015,10(2):0116871.
[26]Lee Y,Phat C,Hong S C. Structural diversity of marine cyclic peptides and their molecular mechanisms for anticancer,antibacterial, antifungal, and other clinical applications.Peptides,2017,95:94-105.
[27] Matsunaga S, Fusetani N, Konosu S. Bioactive marine metabolites VI. structure elucidation of discodermin a, an antimicrobial peptide from the marine sponge discodermia kiiensis. Tetrahedron Letters,1985,25(45):5165-5168.
[28] Oterogonzález A J,Magalh2es B S,Garciavillarino M,et al.Antimicrobial peptides from marine invertebrates as a new frontier for microbial infection control. Faseb Journal,2010,24(5):1320-1334.
[29]Eom S H,Kim Y M,Kim S K. Marine bacteria:potential sources for compounds to overcome antibiotic resistance. Applied Microbiology&Biotechnology,2013,97(11):4763-4773.
[30]Manoharan R K,Brindha P V,Srigopalram S,et al. Studies on a marine Streptomyces fradiae BW2-7 producing glycopeptide antibiotic Vancomycin effective against skin pathogens. Sch Acad J Biosci,2014,2(11):746-761.
[31] Kitani S,Ueguchi T,Igarashi Y,et al. Rakicidin F,a new antibacterial cyclic depsipeptide from a marine sponge-derived Streptomyces sp.. Journal of Antibiotics,2017,71(1):139-141.
[32]Kozuma S,Hirotatakahata Y,Fukuda D,et al. Identification and biological activity of ogipeptins,novel LPS inhibitors produced by marine bacterium. Journal of Antibiotics,2016,70(1):79-83.
[33] Li H Y,Matsunaga S,Fusetani N. Halicylindramides A-C,antifungal and cytotoxic depsipeptides from the marine sponge Halichondria cylindrata. Journal of Medicinal Chemistry,1995,51(8):338-343.
[34]Youssef D T,Shaala L A,Mohamed G A,et al. Theonellamide G,a potent antifungal and cytotoxic bicyclic glycopeptide from the Red Sea marine sponge Theonella swinhoei. Marine Drugs,2014,12(4):1911-1923.
[35]Zhang X,Jacob M R,Rao R R. Antifungal cyclic peptides from the marine sponge microscleroderma herdmani. Res Rep Med Chem,2012,2:7-14
[36] Niggemann J,Bozko P,Bruns N,et al. Baceridin,a cyclic hexapeptide from an epiphytic Bacillus strain, inhibits the proteasome. Chembiochem,2014,15(7):1021-1029.
[37]Ishihara K,Sobue M,Uemura D,et al. N-acetylgalactosamine4,6-bissulfate in rat urine I. Isolation,identification and chemical synthesis. Biochimica Et Biophysica Acta,1976,437(2):416-430.
[38]Kohli R M,Walsh C T,Burkart M D. Biomimetic synthesis and optimization of cyclic peptide antibiotics. Nature,2002,418(6898):658-661.
[39] Von D H,Dieckmann R,Pavela-Vrancic M. The nonribosomal code. Chemistry&Biology,1999,6(10):273-279.
[40] And Q X,Pei D. High-Throughput synthesis and screening of cyclic peptide antibiotics. Journal of Medicinal Chemistry,2007;50(13):3132-3137.
[41]Oddo A,Thomsen T T,Britt H M,et al. Modulation of backbone flexibility for effective dissociation of antibacterial and hemolytic activity in cyclic peptides. Acs Medicinal Chemistry Letters,2016,7(8):741-745.
[42] Abraham T,Prenner E J,Lewis R N,et al. Structure-activity relationships of the antimicrobial peptide gramicidin S and its analogs:aqueous solubility, self-association, conformation,antimicrobial activity and interaction with model lipid membranes.Biochimica et Biophysica acta,2014,1838(5):1420-1429.
[43] Oh D,Sun J,Nasrolahi S A,et al. Antibacterial activities of amphiphilic cyclic cell-penetrating peptides against multidrugresistant pathogens. Molecular Pharmaceutics,2014,11(10):3528-3536.
[44]Falanga A,Nigro E,De Biasi M G,et al. Cyclic peptides as novel therapeutic microbicides:engineering of human defensin mimetics. Molecules,2017,22(7):1217.
[45]Scudiero O,Nigro E,Cantisani M,et al. Design and activity of a cyclic mini-β-defensin analog:a novel antimicrobial tool.International Journal of Nanomedicine,2015,10:6523-6539.
[46] Sun L, Zheng C, Webster T J. Self-assembled peptide nanomaterials for biomedical applications:promises and pitfalls.International Journal of Nanomedicine,2017,12:73-86.
[47]Clark T D,And L K B,Ghadiri M R. Self-assembling cyclicβ3-peptide nanotubes as artificial transmembrane ion channels.Journal of the American Chemical Society,1998,120(4):651-656.
[48] Fernandezlopez S,Kim H S,Choi E C,et al. Antibacterial agents based on the cyclic d,l-|[alpha]|-peptide architecture.Nature,2001,412(6845):452-455.
[49]Zorzi A,Deyle K,Heinis C. Cyclic peptide therapeutics:past,present and future. Current Opinion in Chemical Biology,2017,38:24-29.
[50] Cetinkaya Y, Falk P, Mayhall C G. Vancomycin-resistant enterococci. Clinical Microbiology Reviews,2000,13(4):686-707.
[51]Reynolds P E. Structure,biochemistry and mechanism of action of glycopeptide antibiotics. Clinical Microbiology,1989,8(11):943-950.
[52] Wijesekara P N K,Kumbukgolla W W,Jayaweera J,et al.Review on usage of vancomycin in livestock and humans:maintaining its efficacy,prevention of resistance and alternative therapy. Vet Sci,2017,4(1):6.
[53] Klinker K P,Borgert S J. Beyond vancomycin:the tail of the lipoglycopeptides. Clin Ther,2015,37(12):2619-2636.
[54] Patel S,Ahmed S,Eswari J S. Therapeutic cyclic lipopeptides mining from microbes:latest strides and hurdles. World Journal of Microbiology&Biotechnology,2015,31(8):1177-1193.
[55] Srinivas N,Jetter P,Ueberbacher B J,et al. Peptidomimetic antibiotics target outer-membrane biogenesis in Pseudomonas aeruginosa. Science,2010,327(5968):1010-1013.
[2]Altekruse S F,Cohen M L,Swerdlow D L. Emerging foodborne diseases. Emerging Infectious Diseases,1997,3(3):285-293.
[3]Mor-Mur M,Yuste J. Emerging bacterial pathogens in meat and poultry:An Overview. Food and Bioprocess Technology,2009,3(1):24-35.
[4]Jennings J L,Sait L C,Perrett C A,et al. Campylobacter jejuni is associated with,but not sufficient to cause vibrionic hepatitis in chickens. Vet Microbiol,2011,149(1-2):193-199.
[5] Chaves Hernández A J. Poultry and avian diseases. In:Encyclopedia of agriculture and food systems. Oxford:Academic Press,2014:504-520.
[6]Hoon J S. Cyclic Peptides as therapeutic agents and biochemical tools. Biomolecules&Therapeutics,2012,20(1):19-26.
[7] Borthwick A D. 2,5-Diketopiperazines:synthesis,reactions,medicinal chemistry, and bioactive natural products.Cheminform,2012,112(7):3641-3716.
[8]Listed N. Discovery and applications of naturally occurring cyclic peptides. Drug Discovery Today Technologies,2012,9(1):1-70.
[9]Gause G F,Brazhnikova M G. Gramicidin S and its use in the treatment of infected wounds. Nature,1944,154(3918):703.
[10]Ovchinnikov Y A, Ivanov V T. ChemInform abstract:conformational states and biological activity of cyclic peptides.Tetrahedron,1975,31(18):2177-2209.
[11]Conti E,Stachelhaus T,Marahiel M A,et al. Structural basis for the activation of phenylalanine in the non-ribosomal biosynthesis of gramicidin S. Embo Journal,1997,16(14):4174-4183.
[12] Velkov T,Roberts K D,Nation R L,et al. Pharmacology of polymyxins:new insights into an'old'class of antibiotics. Future Microbiology,2013,8(6):711-724.
[13]Yoshino N,Endo M,Kanno H,et al. Polymyxins as novel and safe mucosal adjuvants to induce humoral immune responses in mice. PLo S One,2013,8(4):225-227.
[14]Schfer M,Schneider T R,Sheldrick G M. Crystal structure of vancomycin. Structure,1996,4(12):1509-1515.
[15]Nicolaou K C,Boddy C N,Brse S,et al. Chemistry,Biology,and Medicine of the Glycopeptide Antibiotics. Angewandte Chemie,1999,30(45):2096-2152.
[16] Liskamp R M J,Rijkers D T S,Bakker S E. Bioactive macrocyclic peptides and peptide mimics. Modern Supramolecular Chemistry:Strategies for Macrocycle Synthesis,2008,1-27.
[17] Armando G R, Andrew S R, Kamal H. Daptomycin:an evidence-based review of its role in the treatment of Gram-positive infections. Infection&Drug Resistance,2016,9(1):47-58.
[18]Kaya S,Yilmaz G,Kalkan A,et al. Treatment of gram-positive left-sided infective endocarditis with daptomycin. Journal of Infection&Chemotherapy,2013,19(4):698-702.
[19] Xing Y,Wang W,Dai S,et al. Daptomycin exerts rapid bactericidal activity against Bacillus anthracis without disrupting membrane integrity. Acta Pharmacologica Sinica,2014,35(2):211-218.
[20] Pogliano J,Pogliano N,Silverman J A. Daptomycin-mediated reorganization of membrane architecture causes mislocalization of essential cell division proteins. Journal of Bacteriology,2012,194(17):4494-4504.
[21] Huang E,Guo Y,Yousef A E. Draft genome sequence of Paenibacillus sp. strain OSY-SE,a bacterium producing the novel broad-spectrum lipopeptide antibiotic paenibacterin. Journal of Bacteriology,2012,194(22):6306.
[22] Huang E,Guo Y,Yousef A E. Biosynthesis of the new broadspectrum lipopeptide antibiotic paenibacterin in Paenibacillus thiaminolyticus OSY-SE. Research in Microbiology,2014,165(3):243-251.
[23] Qin C,Xu C,Zhang R,et al. On-resin cyclization and antimicrobial activity of Laterocidin and its analogues.Tetrahedron Letters,2010,51(9):1257-1261.
[24]Kaweewan I,Hemmi H,Komaki H,et al. Isolation and structure determination of new antibacterial peptide curacomycin based on genome mining. Asian Journal of Organic Chemistry,2017,6(12):1838-1844.
[25]Gong A D,Li H P,Yuan Q S,et al. Antagonistic mechanism of iturin A and plipastatin A from Bacillus amyloliquefaciens S76-3from wheat spikes against Fusarium graminearum. PLo S One,2015,10(2):0116871.
[26]Lee Y,Phat C,Hong S C. Structural diversity of marine cyclic peptides and their molecular mechanisms for anticancer,antibacterial, antifungal, and other clinical applications.Peptides,2017,95:94-105.
[27] Matsunaga S, Fusetani N, Konosu S. Bioactive marine metabolites VI. structure elucidation of discodermin a, an antimicrobial peptide from the marine sponge discodermia kiiensis. Tetrahedron Letters,1985,25(45):5165-5168.
[28] Oterogonzález A J,Magalh2es B S,Garciavillarino M,et al.Antimicrobial peptides from marine invertebrates as a new frontier for microbial infection control. Faseb Journal,2010,24(5):1320-1334.
[29]Eom S H,Kim Y M,Kim S K. Marine bacteria:potential sources for compounds to overcome antibiotic resistance. Applied Microbiology&Biotechnology,2013,97(11):4763-4773.
[30]Manoharan R K,Brindha P V,Srigopalram S,et al. Studies on a marine Streptomyces fradiae BW2-7 producing glycopeptide antibiotic Vancomycin effective against skin pathogens. Sch Acad J Biosci,2014,2(11):746-761.
[31] Kitani S,Ueguchi T,Igarashi Y,et al. Rakicidin F,a new antibacterial cyclic depsipeptide from a marine sponge-derived Streptomyces sp.. Journal of Antibiotics,2017,71(1):139-141.
[32]Kozuma S,Hirotatakahata Y,Fukuda D,et al. Identification and biological activity of ogipeptins,novel LPS inhibitors produced by marine bacterium. Journal of Antibiotics,2016,70(1):79-83.
[33] Li H Y,Matsunaga S,Fusetani N. Halicylindramides A-C,antifungal and cytotoxic depsipeptides from the marine sponge Halichondria cylindrata. Journal of Medicinal Chemistry,1995,51(8):338-343.
[34]Youssef D T,Shaala L A,Mohamed G A,et al. Theonellamide G,a potent antifungal and cytotoxic bicyclic glycopeptide from the Red Sea marine sponge Theonella swinhoei. Marine Drugs,2014,12(4):1911-1923.
[35]Zhang X,Jacob M R,Rao R R. Antifungal cyclic peptides from the marine sponge microscleroderma herdmani. Res Rep Med Chem,2012,2:7-14
[36] Niggemann J,Bozko P,Bruns N,et al. Baceridin,a cyclic hexapeptide from an epiphytic Bacillus strain, inhibits the proteasome. Chembiochem,2014,15(7):1021-1029.
[37]Ishihara K,Sobue M,Uemura D,et al. N-acetylgalactosamine4,6-bissulfate in rat urine I. Isolation,identification and chemical synthesis. Biochimica Et Biophysica Acta,1976,437(2):416-430.
[38]Kohli R M,Walsh C T,Burkart M D. Biomimetic synthesis and optimization of cyclic peptide antibiotics. Nature,2002,418(6898):658-661.
[39] Von D H,Dieckmann R,Pavela-Vrancic M. The nonribosomal code. Chemistry&Biology,1999,6(10):273-279.
[40] And Q X,Pei D. High-Throughput synthesis and screening of cyclic peptide antibiotics. Journal of Medicinal Chemistry,2007;50(13):3132-3137.
[41]Oddo A,Thomsen T T,Britt H M,et al. Modulation of backbone flexibility for effective dissociation of antibacterial and hemolytic activity in cyclic peptides. Acs Medicinal Chemistry Letters,2016,7(8):741-745.
[42] Abraham T,Prenner E J,Lewis R N,et al. Structure-activity relationships of the antimicrobial peptide gramicidin S and its analogs:aqueous solubility, self-association, conformation,antimicrobial activity and interaction with model lipid membranes.Biochimica et Biophysica acta,2014,1838(5):1420-1429.
[43] Oh D,Sun J,Nasrolahi S A,et al. Antibacterial activities of amphiphilic cyclic cell-penetrating peptides against multidrugresistant pathogens. Molecular Pharmaceutics,2014,11(10):3528-3536.
[44]Falanga A,Nigro E,De Biasi M G,et al. Cyclic peptides as novel therapeutic microbicides:engineering of human defensin mimetics. Molecules,2017,22(7):1217.
[45]Scudiero O,Nigro E,Cantisani M,et al. Design and activity of a cyclic mini-β-defensin analog:a novel antimicrobial tool.International Journal of Nanomedicine,2015,10:6523-6539.
[46] Sun L, Zheng C, Webster T J. Self-assembled peptide nanomaterials for biomedical applications:promises and pitfalls.International Journal of Nanomedicine,2017,12:73-86.
[47]Clark T D,And L K B,Ghadiri M R. Self-assembling cyclicβ3-peptide nanotubes as artificial transmembrane ion channels.Journal of the American Chemical Society,1998,120(4):651-656.
[48] Fernandezlopez S,Kim H S,Choi E C,et al. Antibacterial agents based on the cyclic d,l-|[alpha]|-peptide architecture.Nature,2001,412(6845):452-455.
[49]Zorzi A,Deyle K,Heinis C. Cyclic peptide therapeutics:past,present and future. Current Opinion in Chemical Biology,2017,38:24-29.
[50] Cetinkaya Y, Falk P, Mayhall C G. Vancomycin-resistant enterococci. Clinical Microbiology Reviews,2000,13(4):686-707.
[51]Reynolds P E. Structure,biochemistry and mechanism of action of glycopeptide antibiotics. Clinical Microbiology,1989,8(11):943-950.
[52] Wijesekara P N K,Kumbukgolla W W,Jayaweera J,et al.Review on usage of vancomycin in livestock and humans:maintaining its efficacy,prevention of resistance and alternative therapy. Vet Sci,2017,4(1):6.
[53] Klinker K P,Borgert S J. Beyond vancomycin:the tail of the lipoglycopeptides. Clin Ther,2015,37(12):2619-2636.
[54] Patel S,Ahmed S,Eswari J S. Therapeutic cyclic lipopeptides mining from microbes:latest strides and hurdles. World Journal of Microbiology&Biotechnology,2015,31(8):1177-1193.
[55] Srinivas N,Jetter P,Ueberbacher B J,et al. Peptidomimetic antibiotics target outer-membrane biogenesis in Pseudomonas aeruginosa. Science,2010,327(5968):1010-1013.