Acta Veterinaria et Zootechnica Sinica ›› 2020, Vol. 51 ›› Issue (7): 1488-1498.doi: 10.11843/j.issn.0366-6964.2020.07.002
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DONG Zhen, CHEN Chen, LI Bing, ZHOU Xuzheng, ZHANG Jiyu*
Received:
2020-02-26
Online:
2020-07-25
Published:
2020-07-22
CLC Number:
DONG Zhen, CHEN Chen, LI Bing, ZHOU Xuzheng, ZHANG Jiyu. Research Progress of Glycopeptide Antibiotics[J]. Acta Veterinaria et Zootechnica Sinica, 2020, 51(7): 1488-1498.
[1] | FERNANDES P,MARTENS E.Antibiotics in late clinical development[J].Biochem Pharmacol,2017,133:152-163. |
[2] | OUTTERSON K,REX J H,JINKS T,et al.Accelerating global innovation to address antibacterial resistance:introducing CARB-X[J].Nat Rev Drug Discov,2016,15(9):589-590. |
[3] | YAN Q,KARAU M J,RAVAL Y S,et al.In vitro activity of oritavancin in combination with rifampin or gentamicin against prosthetic joint infection-associated methicillin-resistant Staphylococcus epidermidis biofilms[J].Int J Antimicrob Agents,2018,52(5):608-615. |
[4] | BOUZA E,VALERIO M,SORIANO A,et al.Dalbavancin in the treatment of different gram-positive infections:a real-life experience[J].Int J Antimicrob Agents,2018,51(4):571-577. |
[5] | THEURETZBACHER U,OUTTERSON K,ENGEL A,et al.The global preclinical antibacterial pipeline[J].Nat Rev Microbiol,2020,18(5):275-285. |
[6] | MERKEL A B,TEMPLE G K,BURKART M D,et al.Purification,crystallization and preliminary structural studies of DTDP-4-Keto-6-Deoxy-Glucose-5-Epimerase (EvaD) from Amycolatopsis orientalis,the fourth enzyme in the DTDP-L-Epivancosamine biosynthetic pathway[J].Acta Crystallogr D Biol Crystallogr,2002,58(7):1226-1228. |
[7] | AHMED M O,BAPTISTE K E.Vancomycin-resistant enterococci:a review of antimicrobial resistance mechanisms and perspectives of human and animal health[J].Microb Drug Resist,2018,24(5):590-606. |
[8] | DIAZ R,AFREIXO V,RAMALHEIRA E,et al.Evaluation of vancomycin MIC creep in methicillin-resistant Staphylococcus aureus infections-a systematic review and meta-analysis[J].Clin Microbiol Infec,2018,24(2):97-104. |
[9] | RYBAK M J.The pharmacokinetic and pharmacodynamic properties of vancomycin[J].Clin Infect Dis,2006,42(S1):S35-S39. |
[10] | BEACH J E,PERROTT J,TURGEON R D,et al.Penetration of vancomycin into the cerebrospinal fluid:a systematic review[J].Clin Pharmacokinet,2017,56(12):1479-1490. |
[11] | ÁLVAREZ R,CORTÉS L E L,MOLINA J,et al.Optimizing the clinical use of vancomycin[J].Antimicrob Agents Chemother,2016,60(5):2601-2609. |
[12] | ZENG D N,DEBABOV D,HARTSELL T L,et al.Approved glycopeptide antibacterial drugs:mechanism of action and resistance[J].Cold Spring Harb Perspect Med,2016,6(12):a026989. |
[13] | STEGMANN E,FRASCH H J,KILIAN R,et al.Self-resistance mechanisms of Actinomycetes producing lipid II-targeting antibiotics[J].Int J Med Microbiol,2015,305(2):190-195. |
[14] | GARDETE S,TOMASZ A.Mechanisms of vancomycin resistance in Staphylococcus aureus[J].J Clin Invest,2014,124(7):2836-2840. |
[15] | COURVALIN P.Vancomycin resistance in gram-positive cocci[J].Clin Infect Dis,2006,42(S1):S25-S34. |
[16] | LUNDE C S,HARTOUNI S R,JANC J W,et al.Telavancin disrupts the functional integrity of the bacterial membrane through targeted interaction with the cell wall precursor lipid Ⅱ[J].Antimicrob Agents Chemother,2009,53(8):3375-3383. |
[17] | KARLOWSKY J A,NICHOL K,ZHANEL G G.Telavancin:mechanisms of action,in vitro activity,and mechanisms of resistance[J].Clin Infect Dis,2015,61(S2):S58-S68. |
[18] | HILL C M,KRAUSE K M,LEWIS S R,et al.Specificity of induction of the VanA and VanB operons in vancomycin-resistant enterococci by telavancin[J].Antimicrob Agents Chemother,2010,54(7):2814-2818. |
[19] | JONES R N,FLAMM R K,CASTANHEIRA M,et al.Activity of Telavancin against Gram-positive pathogens isolated from bone and joint infections in North American,Latin American,European and Asia-Pacific nations[J].Diagn Microbiol Infect Dis,2017,88(2):184-187. |
[20] | GOLDSTEIN B P,SELVA E,GASTALDO L,et al.A40926,a new glycopeptide antibiotic with anti-Neisseria activity[J].Antimicrob Agents Chemother,1987,31(12):1961-1966. |
[21] | CANDIANI G,ABBONDI M,BORGONOVI M,et al.In-vitro and in-vivo antibacterial activity of BI 397,a new semi-synthetic glycopeptide antibiotic[J].J Antimicrob Chemother,1999,44(2):179-192. |
[22] | MALABARBA A,GOLDSTEIN B P.Origin,structure,and activity in vitro and in vivo of dalbavancin[J].J Antimicrob Chemother,2005,55(S2):ii15-ii20. |
[23] | GARNOCK-JONES K P.Single-dose dalbavancin:a review in acute bacterial skin and skin structure infections[J].Drugs,2017,77(1):75-83. |
[24] | RAPPO U,PUTTAGUNTA S,SHEVCHENKO V,et al.Dalbavancin for the treatment of osteomyelitis in adult patients:a randomized clinical trial of efficacy and safety[J].Open Forum Infect Dis,2019,6(1):ofy331. |
[25] | CERCENADO E.Antimicrobial spectrum of dalbavancin.Mechanism of action and in vitro activity against Gram-positive microorganisms[J].Enferm Infecc Microbiol Clin,2017,35(Sl):9-14. |
[26] | ECONOMOU N J,NAHOUM V,WEEKS S D,et al.A carrier protein strategy yields the structure of dalbavancin[J].J Am Chem Soc,2012,134(10):4637-4645. |
[27] | CHENG M,ZIORA Z M,HANSFORD K A,et al.Anti-cooperative ligand binding and dimerisation in the glycopeptide antibiotic dalbavancin[J].Org Biomol Chem,2014,12(16):2568-2575. |
[28] | ARHIN F F,SEGUIN D L,BELLEY A,et al.In vitro stepwise selection of reduced susceptibility to lipoglycopeptides in enterococci[J].Diagn Microbiol Infect Dis,2017,89(2):168-171. |
[29] | AZANZA J R,SÁDABA B,REIS J.Dalbavancina:pharmacokinetic and pharmacodynamic parameters[J].Enferm Infecc Microbiol ClÍn,2017,35(Sl):22-27. |
[30] | WERTH B J,JAIN R,HAHN A,et al.Emergence of dalbavancin non-susceptible,vancomycin-intermediate Staphylococcus aureus (VISA) after treatment of MRSA central line-associated bloodstream infection with a dalbavancin-and vancomycin-containing regimen[J].Clin Microbiol Infect,2018,24(4):429.e1-429.e5. |
[31] | ALLEN N E.From vancomycin to oritavancin:the discovery and development of a novel lipoglycopeptide antibiotic[J].Anti Infect Agents Med Chem,2010,9(1):23-47. |
[32] | COREY G R,LOUTIT J,MOECK G,et al.Single intravenous dose of oritavancin for treatment of acute skin and skin structure infections caused by gram-positive bacteria:summary of safety analysis from the phase 3 SOLO studies[J].Antimicrob Agents Chemother,2018,62(4):e01919-17. |
[33] | JOHNSON J A,FEENEY E R,KUBIAK D W,et al.Prolonged use of oritavancin for vancomycin-resistant Enterococcus faecium prosthetic valve endocarditis[J].Open Forum Infect Dis,2015,2(4):ofv156. |
[34] | ZHANEL G G,SCHWEIZER F,KARLOWSKY J A.Oritavancin:mechanism of action[J].Clin Infect Dis,2012,54(S3):S214-S219. |
[35] | KIM S J,CEGELSKI L,STUEBER D,et al.Oritavancin exhibits dual mode of action to inhibit cell-wall biosynthesis in Staphylococcus aureus[J].J Mol Biol,2008,377(1):281-293. |
[36] | COOPER M A,WILLIAMS D H.Binding of glycopeptide antibiotics to a model of a vancomycin-resistant bacterium[J].Chem Biol,1999,6(12):891-899. |
[37] | YARLAGADDA V,SAMADDAR S,PARAMANANDHAM K,et al.Membrane disruption and enhanced inhibition of cell-wall biosynthesis:a synergistic approach to tackle vancomycin-resistant bacteria[J].Angew Chem Int Ed,2015,54(46):13644-13649. |
[38] | NICOLAOU K C,BODDY C N C,BRÄSE S,et al.Chemistry,biology,and medicine of the glycopeptide antibiotics[J].Angew Chem Int Ed,1999,38(15):2096-2152. |
[39] | YAO R C,CRANDALL L W.Glycopeptides:classification,occurrence,and discovery[M]//NAGARAJAN R.Glycopeptide Antibiotics.New York:Marcel Dekker,1994:1. |
[40] | WRIGHT L P,PHILIPS M R.Thematic review series:lipid posttranslational modifications CAAX modification and membrane targeting of Ras[J].J Lipid Res,2006,47(5):883-891. |
[41] | MURRAY D,HERMIDA-MATSUMOTO L,BUSER C A,et al.Electrostatics and the membrane association of Src:theory and experiment[J].Biochemistry,1998,37(8):2145-2159. |
[42] | PYLYPENKO O,HAMMICH H,YU I M,et al.Rab GTPases and their interacting protein partners:structural insights into Rab functional diversity[J].Small GTPases,2018,9(1-2):22-48. |
[43] | ZHOU W,PARENT L J,WILLS J W,et al.Identification of a membrane-binding domain within the amino-terminal region of human immunodeficiency virus type 1 gag protein which interacts with acidic phospholipids[J].J Virol,1994,68(4):2556-2569. |
[44] | SEYKORA J T,MYAT M M,ALLEN L A H,et al.Molecular determinants of the myristoyl-electrostatic switch of MARCKS[J].J Biol Chem,1996,271(31):18797-18802. |
[45] | MURRAY D,ARBUZOVA A,HONIG B,et al.The role of electrostatic and nonpolar interactions in the association of peripheral proteins with membranes[J].Curr Top Membr,2002,52:277-307. |
[46] | MCLAUGHLIN S,ADEREM A.The myristoyl-electrostatic switch:a modulator of reversible protein-membrane interactions[J].Trends Biochem Sci,1995,20(7):272-276. |
[47] | BLASKOVICH M A T,HANSFORD K A,GONG Y J,et al.Protein-inspired antibiotics active against vancomycin-and daptomycin-resistant bacteria[J].Nat Commun,2018,9(1):22. |
[48] | CROWLEY B M,BOGER D L.Total synthesis and evaluation of[Ψ[CH2NH]Tpg4]vancomycin aglycon:reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding[J].J Am Chem Soc,2006,128(9):2885-2892. |
[49] | XIE J,PIERCE J G,JAMES R C,et al.A redesigned vancomycin engineered for dual D-Ala-D-Ala And D-Ala-D-Lac binding exhibits potent antimicrobial activity against vancomycin-resistant bacteria[J].J Am Chem Soc,2011,133(35):13946-13949. |
[50] | XIE J,OKANO A,PIERCE J G,et al.Total synthesis of[Ψ[C(=S)NH]Tpg4]Vancomycin Aglycon,[Ψ[C(=NH)NH]Tpg4]Vancomycin aglycon,and related key compounds:reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding[J].J Am Chem Soc,2012,134(2):1284-1297. |
[51] | OKANO A,JAMES R C,PIERCE J G,et al.Silver(I)-promoted conversion of thioamides to amidines:divergent synthesis of a key series of vancomycin aglycon residue 4 amidines that clarify binding behavior to model ligands[J].J Am Chem Soc,2012,134(21):8790-8793. |
[52] | NAKAMA Y,YOSHIDA O,YODA M,et al.Discovery of a novel series of semisynthetic vancomycin derivatives effective against vancomycin-resistant bacteria[J].J Med Chem,2010,53(6):2528-2533. |
[53] | GERHARD U,MACKAY J P,MAPLESTONE R A,et al.The role of the sugar and chlorine substituents in the dimerization of vancomycin antibiotics[J].J Am Chem Soc,1993,115(1):232-237. |
[54] | WADZINSKI T J,GEA K D,MILLER S J.A stepwise dechlorination/cross-coupling strategy to diversify the vancomycin ‘in-chloride’[J].Bioorg Med Chem Lett,2016,26(3):1025-1028. |
[55] | MARSCHALL E,CRYLE M J,TAILHADES J.Biological,chemical,and biochemical strategies for modifying glycopeptide antibiotics[J].J Biol Chem,2019,294(49):18769-18783. |
[56] | ANTONOPLIS A,ZANG X Y,HUTTNER M A,et al.A dual-function antibiotic-transporter conjugate exhibits superior activity in sterilizing MRSA biofilms and killing persister cells[J].J Am Chem Soc,2018,140(47):16140-16151. |
[57] | ANTONOPLIS A,ZANG X Y,WEGNER T,et al.Vancomycin-arginine conjugate inhibits growth of carbapenem-resistant E. coli and targets cell-wall synthesis[J].ACS Chem Biol,2019,14(9):2065-2070. |
[58] | ZMIJEWSKI M J,LOGAN R M,MARCONI G,et al.Biotransformation of vancomycin B to vancomycin hexapeptide by a soil microorganism[J].J Nat Prod,1989,52(1):203-206. |
[59] | BOOTH P M,STONE D J M,WILLIAMS D H.The edman degradation of vancomycin:preparation of vancomycin hexapeptide[J].J Chem Soc Chem Commun,1987(22):1694-1695. |
[60] | BRIEKE C,YIM G,PESCHKE M,et al.Catalytic promiscuity of glycopeptide N-methyltransferases enables bio-orthogonal labelling of biosynthetic intermediates[J].Chem Commun,2016,52(94):13679-13682. |
[61] | PARK O K,CHOI H Y,KIM G W,et al.Generation of new complestatin analogues by heterologous expression of the complestatin biosynthetic gene cluster from Streptomyces chartreusis AN1542[J].ChemBioChem,2016,17(18):1725-1731. |
[62] | YIM G,WANG W L,THAKER M N,et al.How to make a glycopeptide:a synthetic biology approach to expand antibiotic chemical diversity[J].ACS Infect Dis,2016,2(9):642-650. |
[63] | WAGLECHNER N,MCARTHUR A G,WRIGHT G D.Phylogenetic reconciliation reveals the natural history of glycopeptide antibiotic biosynthesis and resistance[J].Nat Microbiol,2019,4(11):1862-1871. |
[64] | THAKER M N,WANG W L,SPANOGIANNOPOULOS P,et al.Identifying producers of antibacterial compounds by screening for antibiotic resistance[J].Nat Biotechnol,2013,31(10):922-927. |
[65] | GUITOR A K,RAPHENYA A R,KLUNK J,et al.Capturing the resistome:a targeted capture method to reveal antibiotic resistance determinants in metagenomes[J].Antimicrob Agents Chemother,2019,64(1):e01324-19. |
[66] | YAN Y,LIU Q K,ZANG X,et al.Resistance-gene-directed discovery of a natural-product herbicide with a new mode of action[J].Nature,2018,559(7714):415-418. |
[67] | TANG X Y,LI J,MILLÁN-AGUIÑAGA N,et al.Identification of thiotetronic acid antibiotic biosynthetic pathways by target-directed genome mining[J].ACS Chem Biol,2015,10(12):2841-2849. |
[68] | CULP E J,WAGLECHNER N,WANG W L,et al.Evolution-guided discovery of antibiotics that inhibit peptidoglycan remodelling[J].Nature,2020,578(7796):582-587. |
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