Tuning of a Membrane-Perforating Antimicrobial Peptide to Selectively Target Membranes of Different Lipid Composition.
Antimicrobial peptides
Bacterial selectivity
Drug-resistant bacteria
Leucine-rich peptide
Pore formation
Protein folding
Journal
The Journal of membrane biology
ISSN: 1432-1424
Titre abrégé: J Membr Biol
Pays: United States
ID NLM: 0211301
Informations de publication
Date de publication:
02 2021
02 2021
Historique:
received:
15
12
2020
accepted:
21
01
2021
pubmed:
11
2
2021
medline:
5
3
2022
entrez:
10
2
2021
Statut:
ppublish
Résumé
The use of designed antimicrobial peptides as drugs has been impeded by the absence of simple sequence-structure-function relationships and design rules. The likely cause is that many of these peptides permeabilize membranes via highly disordered, heterogeneous mechanisms, forming aggregates without well-defined tertiary or secondary structure. We suggest that the combination of high-throughput library screening with atomistic computer simulations can successfully address this challenge by tuning a previously developed general pore-forming peptide into a selective pore-former for different lipid types. A library of 2916 peptides was designed based on the LDKA template. The library peptides were synthesized and screened using a high-throughput orthogonal vesicle leakage assay. Dyes of different sizes were entrapped inside vesicles with varying lipid composition to simultaneously screen for both pore size and affinity for negatively charged and neutral lipid membranes. From this screen, nine different LDKA variants that have unique activity were selected, sequenced, synthesized, and characterized. Despite the minor sequence changes, each of these peptides has unique functional properties, forming either small or large pores and being selective for either neutral or anionic lipid bilayers. Long-scale, unbiased atomistic molecular dynamics (MD) simulations directly reveal that rather than rigid, well-defined pores, these peptides can form a large repertoire of functional dynamic and heterogeneous aggregates, strongly affected by single mutations. Predicting the propensity to aggregate and assemble in a given environment from sequence alone holds the key to functional prediction of membrane permeabilization.
Identifiants
pubmed: 33564914
doi: 10.1007/s00232-021-00174-1
pii: 10.1007/s00232-021-00174-1
doi:
Substances chimiques
Antimicrobial Peptides
0
Lipid Bilayers
0
Peptides
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
75-96Références
Ablan FD, Spaller BL, Abdo KI, Almeida PF (2016) Charge distribution fine-tunes the translocation of alpha-helical amphipathic peptides across membranes. Biophys J 111(8):1738–1749. https://doi.org/10.1016/j.bpj.2016.08.047
doi: 10.1016/j.bpj.2016.08.047
pubmed: 27760360
pmcid: 5071627
Abraham T, Lewis RNAH, Hodges RS, McElhaney RN (2005) Isothermal titration calorimetry studies of the binding of a rationally designed analogue of the antimicrobial peptide gramicidin S to phospholipid bilayer membranes. Biochemistry 44(6):2103–2112. https://doi.org/10.1021/bi048077d
doi: 10.1021/bi048077d
pubmed: 15697236
pmcid: 3245835
Bennett WF, Hong CK, Wang Y, Tieleman DP (2016) Antimicrobial peptide simulations and the influence of force field on the free energy for pore formation in lipid bilayers. J Chem Theory Comput 12(9):4524–4533. https://doi.org/10.1021/acs.jctc.6b00265
doi: 10.1021/acs.jctc.6b00265
pubmed: 27529120
Berkowitz M (2016) Chapter one—a molecular look at membranes. In: Bennett V (ed) Current topics in membranes. Academic Press, New York, pp 1–25
Biswaro LS, da Costa Sousa MG, Rezende TMB, Dias SC, Franco OL (2018) Antimicrobial peptides and nanotechnology, recent advances and challenges. Front Microbiol 9:855. https://doi.org/10.3389/fmicb.2018.00855
doi: 10.3389/fmicb.2018.00855
pubmed: 29867793
pmcid: 5953333
Breukink E, Ganz P, de Kruijff B, Seelig J (2000) Binding of Nisin Z to bilayer vesicles as determined with isothermal titration calorimetry. Biochemistry 39(33):10247–10254. https://doi.org/10.1021/bi000915q
doi: 10.1021/bi000915q
pubmed: 10956014
Cao J, de la Fuente-Nunez C, Ou RW, Torres MT, Pande SG, Sinskey AJ, Lu TK (2018) Yeast-based synthetic biology platform for antimicrobial peptide production. ACS Synth Biol 7(3):896–902. https://doi.org/10.1021/acssynbio.7b00396
doi: 10.1021/acssynbio.7b00396
pubmed: 29366323
Cardoso MH, Orozco RQ, Rezende SB, Rodrigues G, Oshiro KGN, Candido ES, Franco OL (2019) Computer-aided design of antimicrobial peptides: are we generating effective drug candidates? Front Microbiol 10:3097. https://doi.org/10.3389/fmicb.2019.03097
doi: 10.3389/fmicb.2019.03097
pubmed: 32038544
Carney RP, Thillier Y, Kiss Z, Sahabi A, Heleno Campos JC, Knudson A, Liu R, Olivos D, Saunders M, Tian L, Lam KS (2017) Combinatorial library screening with liposomes for discovery of membrane active peptides. ACS Comb Sci 19(5):299–307. https://doi.org/10.1021/acscombsci.6b00182
doi: 10.1021/acscombsci.6b00182
pubmed: 28378995
pmcid: 5901688
Chen CH, Lu TK (2020) Development and challenges of antimicrobial peptides for therapeutic applications. Antibiotics (Basel). https://doi.org/10.3390/antibiotics9010024
doi: 10.3390/antibiotics9010024
pmcid: 7824093
Chen CH, Wiedman G, Khan A, Ulmschneider MB (2014) Absorption and folding of melittin onto lipid bilayer membranes via unbiased atomic detail microsecond molecular dynamics simulation. Biochim Biophys Acta 1838(9):2243–2249. https://doi.org/10.1016/j.bbamem.2014.04.012
doi: 10.1016/j.bbamem.2014.04.012
pubmed: 24769159
Chen CH, Khan A, Huang JJ, Ulmschneider MB (2016) Mechanisms of membrane pore formation by amyloidogenic peptides in amyotrophic lateral sclerosis. Chemistry 22(29):9958–9961. https://doi.org/10.1002/chem.201601765
doi: 10.1002/chem.201601765
pubmed: 27224887
Chen C, Starr CG, Troendle EP, Wiedman G, Wimley WC, Ulmschneider JP, Ulmschneider MB (2019) Simulation-guided rational de novo design of a small pore-forming antimicrobial peptide. J Am Chem Soc. https://doi.org/10.1021/jacs.8b11939
doi: 10.1021/jacs.8b11939
pubmed: 31854979
pmcid: 7928070
Chen CH, Ulmschneider JP, Ulmschneider MB (2020a) Mechanisms of a small membrane-active antimicrobial peptide from Hyla punctata. Aust J Chem 73(3):236–245
doi: 10.1071/CH19429
Chen CH, Melo MC, Berglund N, Khan A, de la Fuente C, Ulmschneider JP, Ulmschneider MB (2020b) Understanding and modelling the interactions of peptides with membranes: from partitioning to self-assembly. Curr Opin Struct Biol 61:160–166. https://doi.org/10.1016/j.sbi.2019.12.021
doi: 10.1016/j.sbi.2019.12.021
pubmed: 32006812
Costerton JW, Stewart PS, Greenberg EP (1999) Bacterial biofilms: a common cause of persistent infections. Science 284(5418):1318–1322
doi: 10.1126/science.284.5418.1318
Dempsey CE, Bazzo R, Harvey TS, Syperek I, Boheim G, Campbell ID (1991) Contribution of proline-14 to the structure and actions of melittin. FEBS Lett 281(1–2):240–244
doi: 10.1016/0014-5793(91)80402-O
Drlica K, Zhao X (1997) DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev 61(3):377–392
doi: 10.1128/.61.3.377-392.1997
Eisenberg D, Weiss RM, Terwilliger TC (1982) The helical hydrophobic moment: a measure of the amphiphilicity of a helix. Nature 299(5881):371–374
doi: 10.1038/299371a0
Fernandez DI, Lee TH, Sani MA, Aguilar MI, Separovic F (2013) Proline facilitates membrane insertion of the antimicrobial peptide maculatin 1.1 via surface indentation and subsequent lipid disordering. Biophys J 104(7):1495–1507. https://doi.org/10.1016/j.bpj.2013.01.059
doi: 10.1016/j.bpj.2013.01.059
pubmed: 23561526
pmcid: 3617439
Fleeman RM, Macias LA, Brodbelt JS, Davies BW (2020) Defining principles that influence antimicrobial peptide activity against capsulated Klebsiella pneumoniae. Proc Natl Acad Sci USA 117(44):27620–27626. https://doi.org/10.1073/pnas.2007036117
doi: 10.1073/pnas.2007036117
pubmed: 33087568
Gong H, Zhang J, Hu X, Li Z, Fa K, Liu H, Waigh TA, McBain A, Lu JR (2019) Hydrophobic control of the bioactivity and cytotoxicity of de novo-designed antimicrobial peptides. ACS Appl Mater Interfaces 11(38):34609–34620. https://doi.org/10.1021/acsami.9b10028
doi: 10.1021/acsami.9b10028
pubmed: 31448889
Grau-Campistany A, Strandberg E, Wadhwani P, Reichert J, Bürck J, Rabanal F, Ulrich AS (2015) Hydrophobic mismatch demonstrated for membranolytic peptides, and their use as molecular rulers to measure bilayer thickness in native cells. Sci Rep 5:9388. https://doi.org/10.1038/srep09388
doi: 10.1038/srep09388
pubmed: 25807192
pmcid: 5224518
Grau-Campistany A, Strandberg E, Wadhwani P, Rabanal F, Ulrich AS (2016) Extending the hydrophobic mismatch concept to amphiphilic membranolytic peptides. J Phys Chem Lett 7(7):1116–1120. https://doi.org/10.1021/acs.jpclett.6b00136
doi: 10.1021/acs.jpclett.6b00136
pubmed: 26963560
Guha S, Ghimire J, Wu E, Wimley WC (2019) Mechanistic landscape of membrane-permeabilizing peptides. Chem Rev. https://doi.org/10.1021/acs.chemrev.8b00520
doi: 10.1021/acs.chemrev.8b00520
pubmed: 30624911
Hahn FE, Sarre SG (1969) Mechanism of action of gentamicin. J Infect Dis 119(4):364–369
doi: 10.1093/infdis/119.4-5.364
Hall-Stoodley L, Costerton JW, Stoodley P (2004) Bacterial biofilms: from the natural environment to infectious diseases. Nat Rev Microbiol 2(2):95–108. https://doi.org/10.1038/nrmicro821
doi: 10.1038/nrmicro821
pubmed: 15040259
Haney EF, Brito-Sanchez Y, Trimble MJ, Mansour SC, Cherkasov A, Hancock REW (2018) Computer-aided discovery of peptides that specifically attack bacterial biofilms. Sci Rep 8(1):1871. https://doi.org/10.1038/s41598-018-19669-4
doi: 10.1038/s41598-018-19669-4
pubmed: 29382854
pmcid: 5789975
Hartrampf N, Saebi A, Poskus M, Gates ZP, Callahan AJ, Cowfer AE, Hanna S, Antilla S, Schissel CK, Quartararo AJ, Ye X, Mijalis AJ, Simon MD, Loas A, Liu S, Jessen C, Nielsen TE, Pentelute BL (2020) Synthesis of proteins by automated flow chemistry. Science 368(6494):980–987. https://doi.org/10.1126/science.abb2491
doi: 10.1126/science.abb2491
pubmed: 32467387
Hu X, Liao M, Gong H, Zhang L, Cox H, Waigh TA, Jian RLu (2020) Recent advances in short peptide self-assembly: from rational design to novel applications. Curr Opin Colloid Interface Sci 45:1–13. https://doi.org/10.1016/j.cocis.2019.08.003
doi: 10.1016/j.cocis.2019.08.003
Huang HW (2020) DAPTOMYCIN, its membrane-active mechanism vs. that of other antimicrobial peptides. Biochim Biophys Acta 1862(10):183395. https://doi.org/10.1016/j.bbamem.2020.183395
doi: 10.1016/j.bbamem.2020.183395
Huang J, MacKerell AD (2013) CHARMM36 all-atom additive protein force field: validation based on comparison to NMR data. J Comput Chem 34(25):2135–2145. https://doi.org/10.1002/jcc.23354
doi: 10.1002/jcc.23354
pubmed: 23832629
pmcid: 3800559
Huang HW, Charron NE (2017) Understanding membrane-active antimicrobial peptides. Q Rev Biophys 50:e10. https://doi.org/10.1017/S0033583517000087
doi: 10.1017/S0033583517000087
pubmed: 29233222
Humphrey W, Dalke A, Schulten K (1996) VMD: visual molecular dynamics. J Mol Graph 14(1):33–38. https://doi.org/10.1016/0263-7855(96)00018-5
doi: 10.1016/0263-7855(96)00018-5
pubmed: 8744570
Jorgensen WL, Chandrasekhar J, Madura JD (1983) Comparison of simple potential functions for simulating liquid water. J Chem Phys 79:926–935
doi: 10.1063/1.445869
Kim SY, Pittman AE, Zapata-Mercado E, King GM, Wimley WC, Hristova K (2019) Mechanism of action of peptides that cause the pH-triggered macromolecular poration of lipid bilayers. J Am Chem Soc 141(16):6706–6718. https://doi.org/10.1021/jacs.9b01970
doi: 10.1021/jacs.9b01970
pubmed: 30916949
Krauson AJ, He J, Wimley WC (2012) Gain-of-function analogues of the pore-forming peptide melittin selected by orthogonal high-throughput screening. J Am Chem Soc 134(30):12732–12741. https://doi.org/10.1021/ja3042004
doi: 10.1021/ja3042004
pubmed: 22731650
pmcid: 3443472
Krauson AJ, Hall OM, Fuselier T, Starr CG, Kauffman WB, Wimley WC (2015) Conformational fine-tuning of pore-forming peptide potency and selectivity. J Am Chem Soc 137(51):16144–16152. https://doi.org/10.1021/jacs.5b10595
doi: 10.1021/jacs.5b10595
pubmed: 26632653
pmcid: 4697923
Ladokhin AS, Wimley WC, White SH (1995) Leakage of membrane vesicle contents: determination of mechanism using fluorescence requenching. Biophys J 69(5):1964–1971. https://doi.org/10.1016/S0006-3495(95)80066-4
doi: 10.1016/S0006-3495(95)80066-4
pubmed: 8580339
pmcid: 1236429
Ladokhin AS, Jayasinghe S, White SH (2000) How to measure and analyze tryptophan fluorescence in membranes properly, and why bother? Anal Biochem 285(2):235–245. https://doi.org/10.1006/abio.2000.4773
doi: 10.1006/abio.2000.4773
pubmed: 11017708
Lakshmaiah Narayana J, Mishra B, Lushnikova T, Wu Q, Chhonker YS, Zhang Y, Zarena D, Salnikov ES, Dang X, Wang F, Murphy C, Foster KW, Gorantla S, Bechinger B, Murry DJ, Wang G (2020) Two distinct amphipathic peptide antibiotics with systemic efficacy. Proc Natl Acad Sci USA 117(32):19446–19454. https://doi.org/10.1073/pnas.2005540117
doi: 10.1073/pnas.2005540117
pubmed: 32723829
Laursen RA (1971) Solid-phase Edman degradation. An automatic peptide sequencer. Eur J Biochem 20(1):89–102
doi: 10.1111/j.1432-1033.1971.tb01366.x
Lazzaro BP, Zasloff M, Rolff J (2020) Antimicrobial peptides: application informed by evolution. Science. https://doi.org/10.1126/science.aau5480
doi: 10.1126/science.aau5480
pubmed: 32355003
Lee J, Cheng X, Swails JM, Yeom MS, Eastman PK, Lemkul JA, Wei S, Buckner J, Jeong JC, Qi Y, Jo S, Pande VS, Case DA, Brooks CL, MacKerell AD, Klauda JB, Im W (2016) CHARMM-GUI input generator for NAMD, GROMACS, AMBER, OpenMM, and CHARMM/OpenMM simulations using the CHARMM36 additive force field. J Chem Theory Comput 12(1):405–413. https://doi.org/10.1021/acs.jctc.5b00935
doi: 10.1021/acs.jctc.5b00935
pubmed: 26631602
Lee AC, Harris JL, Khanna KK, Hong JH (2019) A comprehensive review on current advances in peptide drug development and design. Int J Mol Sci. https://doi.org/10.3390/ijms20102383
doi: 10.3390/ijms20102383
pubmed: 31905822
pmcid: 6981608
Lehrer RI, Barton A, Daher KA, Harwig SS, Ganz T, Selsted ME (1989) Interaction of human defensins with Escherichia coli. Mechanism of bactericidal activity. J Clin Invest 84(2):553–561. https://doi.org/10.1172/JCI114198
doi: 10.1172/JCI114198
pubmed: 2668334
pmcid: 548915
Lei J, Sun L, Huang S, Zhu C, Li P, He J, Mackey V, Coy DH, He Q (2019) The antimicrobial peptides and their potential clinical applications. Am J Transl Res 11(7):3919–3931
pubmed: 31396309
pmcid: 6684887
Leveritt JM 3rd, Pino-Angeles A, Lazaridis T (2015) The structure of a melittin-stabilized pore. Biophys J 108(10):2424–2426. https://doi.org/10.1016/j.bpj.2015.04.006
doi: 10.1016/j.bpj.2015.04.006
pubmed: 25992720
pmcid: 4457010
Li S, Kim SY, Pittman AE, King GM, Wimley WC, Hristova K (2018) Potent macromolecule-sized poration of lipid bilayers by the macrolittins, a synthetically evolved family of pore-forming peptides. J Am Chem Soc 140(20):6441–6447. https://doi.org/10.1021/jacs.8b03026
doi: 10.1021/jacs.8b03026
pubmed: 29694775
Libardo MDJ, Bahar AA, Ma B, Fu R, McCormick LE, Zhao J, McCallum SA, Nussinov R, Ren D, Angeles-Boza AM, Cotten ML (2017) Nuclease activity gives an edge to host-defense peptide piscidin 3 over piscidin 1, rendering it more effective against persisters and biofilms. FEBS J 284(21):3662–3683. https://doi.org/10.1111/febs.14263
doi: 10.1111/febs.14263
pubmed: 28892294
pmcid: 6361529
Lipkin R, Pino-Angeles A, Lazaridis T (2017) Transmembrane pore structures of β-hairpin antimicrobial peptides by all-atom simulations. J Phys Chem B 121(39):9126–9140. https://doi.org/10.1021/acs.jpcb.7b06591
doi: 10.1021/acs.jpcb.7b06591
pubmed: 28879767
pmcid: 5686775
Lobley A, Whitmore L, Wallace BA (2002) DICHROWEB: an interactive website for the analysis of protein secondary structure from circular dichroism spectra. Bioinformatics 18(1):211–212. https://doi.org/10.1093/bioinformatics/18.1.211
doi: 10.1093/bioinformatics/18.1.211
pubmed: 11836237
Luzzatto L, Apirion D, Schlessinger D (1968) Mechanism of action of streptomycin in E. coli: interruption of the ribosome cycle at the initiation of protein synthesis. Proc Natl Acad Sci USA 60(3):873–880
doi: 10.1073/pnas.60.3.873
MacDonald RC, MacDonald RI, Menco BP, Takeshita K, Subbarao NK, Hu LR (1991) Small-volume extrusion apparatus for preparation of large, unilamellar vesicles. Biochim Biophys Acta 1061(2):297–303. https://doi.org/10.1016/0005-2736(91)90295-j
doi: 10.1016/0005-2736(91)90295-j
pubmed: 1998698
Magana M, Pushpanathan M, Santos AL, Leanse L, Fernandez M, Ioannidis A, Giulianotti MA, Apidianakis Y, Bradfute S, Ferguson AL, Cherkasov A, Seleem MN, Pinilla C, de la Fuente-Nunez C, Lazaridis T, Dai T, Houghten RA, Hancock REW, Tegos GP (2020) The value of antimicrobial peptides in the age of resistance. Lancet Infect Dis 20(9):e216–e230. https://doi.org/10.1016/S1473-3099(20)30327-3
doi: 10.1016/S1473-3099(20)30327-3
pubmed: 32653070
Maria-Neto S, de Almeida KC, Macedo MLR, Franco OL (2015) Understanding bacterial resistance to antimicrobial peptides: from the surface to deep inside. Biochim Biophys Acta 1848(11 Pt B):3078–88. https://doi.org/10.1016/j.bbamem.2015.02.017
doi: 10.1016/j.bbamem.2015.02.017
pubmed: 25724815
McCarter JD, Stephens D, Shoemaker K, Rosenberg S, Kirsch JF, Georgiou G (2004) Substrate specificity of the Escherichia coli outer membrane protease OmpT. J Bacteriol 186(17):5919–5925. https://doi.org/10.1128/JB.186.17.5919-5925.2004
doi: 10.1128/JB.186.17.5919-5925.2004
pubmed: 15317797
pmcid: 516829
Mihailescu M, Sorci M, Seckute J, Silin VI, Hammer J, Perrin BS Jr, Hernandez JI, Smajic N, Shrestha A, Bogardus KA, Greenwood AI, Fu R, Blazyk J, Pastor RW, Nicholson LK, Belfort G, Cotten ML (2019) Structure and function in antimicrobial piscidins: histidine position, directionality of membrane insertion, and pH-dependent permeabilization. J Am Chem Soc 141(25):9837–9853. https://doi.org/10.1021/jacs.9b00440
doi: 10.1021/jacs.9b00440
pubmed: 31144503
pmcid: 7312726
Mijalis AJ, Thomas DA, Simon MD, Adamo A, Beaumont R, Jensen KF, Pentelute BL (2017) A fully automated flow-based approach for accelerated peptide synthesis. Nat Chem Biol 13(5):464–466. https://doi.org/10.1038/nchembio.2318
doi: 10.1038/nchembio.2318
pubmed: 28244989
Mishra B, Wang G (2012) Ab initio design of potent anti-MRSA peptides based on database filtering technology. J Am Chem Soc 134(30):12426–12429. https://doi.org/10.1021/ja305644e
doi: 10.1021/ja305644e
pubmed: 22803960
pmcid: 3412535
Mishra B, Lakshmaiah Narayana J, Lushnikova T, Wang X, Wang G (2019) Low cationicity is important for systemic in vivo efficacy of database-derived peptides against drug-resistant Gram-positive pathogens. Proc Natl Acad Sci USA 116(27):13517–13522. https://doi.org/10.1073/pnas.1821410116
doi: 10.1073/pnas.1821410116
pubmed: 31209048
Nešuta O, Hexnerová R, Buděšínský M, Slaninová J, Bednárová L, Hadravová R, Straka J, Veverka V, Čeřovský V (2016) Antimicrobial peptide from the wild bee hylaeus signatus venom and its analogues: structure-activity study and synergistic effect with antibiotics. J Nat Prod 79(4):1073–1083. https://doi.org/10.1021/acs.jnatprod.5b01129
doi: 10.1021/acs.jnatprod.5b01129
pubmed: 26998557
O’Toole GA (2011) Microtiter dish biofilm formation assay. J Vis Exp. https://doi.org/10.3791/2437
doi: 10.3791/2437
pubmed: 21307833
pmcid: 3182663
Perrin BS, Pastor RW (2016) Simulations of membrane-disrupting peptides I: alamethicin pore stability and spontaneous insertion. Biophys J 111(6):1248–1257. https://doi.org/10.1016/j.bpj.2016.08.014
doi: 10.1016/j.bpj.2016.08.014
pubmed: 27653483
pmcid: 5034365
Perrin BS Jr, Fu R, Cotten ML, Pastor RW (2016) Simulations of membrane-disrupting peptides II: AMP piscidin 1 favors surface defects over pores. Biophys J 111(6):1258–1266. https://doi.org/10.1016/j.bpj.2016.08.015
doi: 10.1016/j.bpj.2016.08.015
pubmed: 27653484
pmcid: 5034716
Pino-Angeles A, Leveritt JM III, Themis L (2016) Pore structure and synergy in antimicrobial peptides of the magainin family. PLoS Comput Biol 12(1):e1004570. https://doi.org/10.1371/journal.pcbi.1004570
doi: 10.1371/journal.pcbi.1004570
Pino-Angeles A, Lazaridis T (2018) Effects of peptide charge, orientation, and concentration on melittin transmembrane pores. Biophys J 114(12):2865–2874. https://doi.org/10.1016/j.bpj.2018.05.006
doi: 10.1016/j.bpj.2018.05.006
pubmed: 29925023
pmcid: 6026367
Porto WF, Irazazabal L, Alves ESF, Ribeiro SM, Matos CO, Pires ÁS, Fensterseifer ICM, Miranda VJ, Haney EF, Humblot V, Torres MDT, Hancock REW, Liao LM, Ladram A, Lu TK, de la Fuente-Nunez C, Franco OL (2018) In silico optimization of a guava antimicrobial peptide enables combinatorial exploration for peptide design. Nat Commun 9(1):1490. https://doi.org/10.1038/s41467-018-03746-3
doi: 10.1038/s41467-018-03746-3
pubmed: 29662055
pmcid: 5902452
Prates MV, Sforca ML, Regis WC, Leite JR, Silva LP, Pertinhez TA, Araujo AL, Azevedo RB, Spisni A, Bloch C Jr (2004) The NMR-derived solution structure of a new cationic antimicrobial peptide from the skin secretion of the anuran Hyla punctata. J Biol Chem 279(13):13018–13026. https://doi.org/10.1074/jbc.M310838200
doi: 10.1074/jbc.M310838200
pubmed: 14715660
Pronk S, Páll S, Schulz R, Larsson P, Bjelkmar P, Apostolov R, Shirts MR, Smith JC, Kasson PM, van der Spoel D, Hess B, Lindahl E (2013) GROMACS 4.5: a high-throughput and highly parallel open source molecular simulation toolkit. Bioinformatics 29(7):845–854. https://doi.org/10.1093/bioinformatics/btt055
doi: 10.1093/bioinformatics/btt055
pubmed: 23407358
pmcid: 3605599
Quartararo AJ, Gates ZP, Somsen BA, Hartrampf N, Ye X, Shimada A, Kajihara Y, Ottmann C, Pentelute BL (2020) Ultra-large chemical libraries for the discovery of high-affinity peptide binders. Nat Commun 11(1):3183. https://doi.org/10.1038/s41467-020-16920-3
doi: 10.1038/s41467-020-16920-3
pubmed: 32576815
pmcid: 7311396
Rathinakumar R, Wimley WC (2008) Biomolecular engineering by combinatorial design and high-throughput screening: small, soluble peptides that permeabilize membranes. J Am Chem Soc 130(30):9849–9858. https://doi.org/10.1021/ja8017863
doi: 10.1021/ja8017863
pubmed: 18611015
pmcid: 2582735
Reißer S, Strandberg E, Steinbrecher T, Ulrich AS (2014) 3D hydrophobic moment vectors as a tool to characterize the surface polarity of amphiphilic peptides. Biophys J 106(11):2385–2394. https://doi.org/10.1016/j.bpj.2014.04.020
doi: 10.1016/j.bpj.2014.04.020
pubmed: 24896117
pmcid: 4052240
Rex S (2000) A Pro –> Ala substitution in melittin affects self-association, membrane binding and pore-formation kinetics due to changes in structural and electrostatic properties. Biophys Chem 85(2–3):209–228
doi: 10.1016/S0301-4622(00)00121-6
Richards DM, Brogden RN (1985) Ceftazidime. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs 29(2):105–161
doi: 10.2165/00003495-198529020-00002
Rodnin MV, Vasquez-Montes V, Nepal B, Ladokhin AS, Lazaridis T (2020) Experimental and computational characterization of oxidized and reduced protegrin pores in lipid bilayers. J Membr Biol 253(3):287–298. https://doi.org/10.1007/s00232-020-00124-3
doi: 10.1007/s00232-020-00124-3
pubmed: 32500172
Rodríguez-Rojas A, Moreno-Morales J, Mason AJ, Rolff J (2018) Cationic antimicrobial peptides do not change recombination frequency in Escherichia coli. Biol Lett. https://doi.org/10.1098/rsbl.2018.0006
doi: 10.1098/rsbl.2018.0006
pubmed: 29563281
pmcid: 5897613
Sani MA, Lee TH, Aguilar MI, Separovic F (2015) Proline-15 creates an amphipathic wedge in maculatin 1.1 peptides that drives lipid membrane disruption. Biochim Biophys Acta 1848(10 Pt A):2277–89. https://doi.org/10.1016/j.bbamem.2015.06.013
doi: 10.1016/j.bbamem.2015.06.013
pubmed: 26079051
Sepehri A, PeBenito L, Pino-Angeles A, Lazaridis T (2020) What makes a good pore former: a study of synthetic melittin derivatives. Biophys J 118(8):1901–1913. https://doi.org/10.1016/j.bpj.2020.02.024
doi: 10.1016/j.bpj.2020.02.024
pubmed: 32183940
Simon MD, Heider PL, Adamo A, Vinogradov AA, Mong SK, Li X, Berger T, Policarpo RL, Zhang C, Zou Y, Liao X, Spokoyny AM, Jensen KF, Pentelute BL (2014) Rapid flow-based peptide synthesis. ChemBioChem 15(5):713–720. https://doi.org/10.1002/cbic.201300796
doi: 10.1002/cbic.201300796
pubmed: 24616230
pmcid: 4045704
Stewart PS, Costerton JW (2001) Antibiotic resistance of bacteria in biofilms. Lancet 358(9276):135–138
doi: 10.1016/S0140-6736(01)05321-1
Tieleman DP (2017) Antimicrobial peptides in the cross hairs of computer simulations. Biophys J 113(1):1–3. https://doi.org/10.1016/j.bpj.2017.06.004
doi: 10.1016/j.bpj.2017.06.004
pubmed: 28700907
pmcid: 5510917
Torres MT, de la Fuente-Nunez C (2019) Toward computer-made artificial antibiotics. Curr Opin Microbiol 51:30–38. https://doi.org/10.1016/j.mib.2019.03.004
doi: 10.1016/j.mib.2019.03.004
pubmed: 31082661
Torres MDT, Pedron CN, Higashikuni Y, Kramer RM, Cardoso MH, Oshiro KGN, Franco OL, Silva Junior PI, Silva FD, Oliveira Junior VX, Lu TK, de la Fuente-Nunez C (2018) Structure-function-guided exploration of the antimicrobial peptide polybia-CP identifies activity determinants and generates synthetic therapeutic candidates. Commun Biol 1:221. https://doi.org/10.1038/s42003-018-0224-2
doi: 10.1038/s42003-018-0224-2
pubmed: 30534613
pmcid: 6286318
Ulmschneider JP (2017) Charged antimicrobial peptides can translocate across membranes without forming channel-like pores. Biophys J 113(1):73–81. https://doi.org/10.1016/j.bpj.2017.04.056
doi: 10.1016/j.bpj.2017.04.056
pubmed: 28700927
pmcid: 5510918
Ulmschneider MB, Ulmschneider JP (2008) Folding peptides into lipid bilayer membranes. J Chem Theory Comput 4(11):1807–1809. https://doi.org/10.1021/ct800100m
doi: 10.1021/ct800100m
pubmed: 26620324
Ulmschneider MB, Doux JP, Killian JA, Smith JC, Ulmschneider JP (2010) Mechanism and kinetics of peptide partitioning into membranes from all-atom simulations of thermostable peptides. J Am Chem Soc 132(10):3452–3460. https://doi.org/10.1021/ja909347x
doi: 10.1021/ja909347x
pubmed: 20163187
Ulmschneider JP, Smith JC, White SH, Ulmschneider MB (2011) In silico partitioning and transmembrane insertion of hydrophobic peptides under equilibrium conditions. J Am Chem Soc 133(39):15487–15495. https://doi.org/10.1021/ja204042f
doi: 10.1021/ja204042f
pubmed: 21861483
pmcid: 3191535
Ulmschneider MB, Ulmschneider JP, Schiller N, Wallace BA, von Heijne G, White SH (2014) Spontaneous transmembrane helix insertion thermodynamically mimics translocon-guided insertion. Nat Commun 5:4863. https://doi.org/10.1038/ncomms5863
doi: 10.1038/ncomms5863
pubmed: 25204588
pmcid: 4161982
Ulmschneider JP, Smith JC, White SH, Ulmschneider MB (2018) The importance of the membrane interface as the reference state for membrane protein stability. Biochim Biophys Acta (BBA) 1860(12):2539–2548. https://doi.org/10.1016/j.bbamem.2018.09.012
doi: 10.1016/j.bbamem.2018.09.012
Vinogradov AA, Gates ZP, Zhang C, Quartararo AJ, Halloran KH, Pentelute BL (2017) Library design-facilitated high-throughput sequencing of synthetic peptide libraries. ACS Comb Sci 19(11):694–701. https://doi.org/10.1021/acscombsci.7b00109
doi: 10.1021/acscombsci.7b00109
pubmed: 28892357
pmcid: 5818986
Walther TH, Ulrich AS (2014) Transmembrane helix assembly and the role of salt bridges. Curr Opin Struct Biol 27:63–68. https://doi.org/10.1016/j.sbi.2014.05.003
doi: 10.1016/j.sbi.2014.05.003
pubmed: 24907460
Wang G, Li X, Wang Z (2016) APD3: the antimicrobial peptide database as a tool for research and education. Nucleic Acids Res 44(D1):D1087–D1093. https://doi.org/10.1093/nar/gkv1278
doi: 10.1093/nar/gkv1278
pubmed: 26602694
Wang Y, Chen CH, Hu D, Ulmschneider MB, Ulmschneider JP (2016) Spontaneous formation of structurally diverse membrane channel architectures from a single antimicrobial peptide. Nat Commun 7:13535. https://doi.org/10.1038/ncomms13535
doi: 10.1038/ncomms13535
pubmed: 27874004
pmcid: 5121426
White SH, Wimley WC (1998) Hydrophobic interactions of peptides with membrane interfaces. Biochim Biophys Acta 1376(3):339–352
doi: 10.1016/S0304-4157(98)00021-5
White SH, Wimley WC (1999) Membrane protein folding and stability: physical principles. Annu Rev Biophys Biomol Struct 28:319–365. https://doi.org/10.1146/annurev.biophys.28.1.319
doi: 10.1146/annurev.biophys.28.1.319
pubmed: 10410805
White SH, Wimley WC, Ladokhin AS, Hristova K (1998) Protein folding in membranes: determining energetics of peptide-bilayer interactions. Methods Enzymol 295:62–87. https://doi.org/10.1016/s0076-6879(98)95035-2
doi: 10.1016/s0076-6879(98)95035-2
pubmed: 9750214
Whitmore L, Wallace BA (2004) DICHROWEB, an online server for protein secondary structure analyses from circular dichroism spectroscopic data. Nucleic Acids Res 32(Web Server issue):W668–W673. https://doi.org/10.1093/nar/gkh371
doi: 10.1093/nar/gkh371
pubmed: 15215473
pmcid: 441509
Whitmore L, Wallace BA (2008) Protein secondary structure analyses from circular dichroism spectroscopy: methods and reference databases. Biopolymers 89(5):392–400. https://doi.org/10.1002/bip.20853
doi: 10.1002/bip.20853
pubmed: 17896349
Wibowo D, Zhao CX (2019) Recent achievements and perspectives for large-scale recombinant production of antimicrobial peptides. Appl Microbiol Biotechnol 103(2):659–671. https://doi.org/10.1007/s00253-018-9524-1
doi: 10.1007/s00253-018-9524-1
pubmed: 30470869
Wiedman G, Wimley WC, Hristova K (2015) Testing the limits of rational design by engineering pH sensitivity into membrane-active peptides. Biochim Biophys Acta 1848(4):951–957. https://doi.org/10.1016/j.bbamem.2014.12.023
doi: 10.1016/j.bbamem.2014.12.023
pubmed: 25572997
pmcid: 4331263
Wiedman G, Fuselier T, He J, Searson PC, Hristova K, Wimley WC (2014) Highly efficient macromolecule-sized poration of lipid bilayers by a synthetically evolved peptide. J Am Chem Soc 136(12):4724–4731. https://doi.org/10.1021/ja500462s
doi: 10.1021/ja500462s
pubmed: 24588399
pmcid: 3985440
Wiedman G, Kim SY, Zapata-Mercado E, Wimley WC, Hristova K (2017) pH-triggered, macromolecule-sized poration of lipid bilayers by synthetically evolved peptides. J Am Chem Soc 139(2):937–945. https://doi.org/10.1021/jacs.6b11447
doi: 10.1021/jacs.6b11447
pubmed: 28001058
pmcid: 5521809
Willyard C (2017) The drug-resistant bacteria that pose the greatest health threats. Nature 543(7643):15. https://doi.org/10.1038/nature.2017.21550
doi: 10.1038/nature.2017.21550
pubmed: 28252092
Wimley WC, White SH (1996) Experimentally determined hydrophobicity scale for proteins at membrane interfaces. Nat Struct Biol 3(10):842–848
doi: 10.1038/nsb1096-842
Wimley WC, Selsted ME, White SH (1994) Interactions between human defensins and lipid bilayers: evidence for formation of multimeric pores. Protein Sci 3(9):1362–1373. https://doi.org/10.1002/pro.5560030902
doi: 10.1002/pro.5560030902
pubmed: 7833799
pmcid: 2142938
Wimley WC, Creamer TP, White SH (1996) Solvation energies of amino acid side chains and backbone in a family of host-guest pentapeptides. Biochemistry 35(16):5109–5124. https://doi.org/10.1021/bi9600153
doi: 10.1021/bi9600153
pubmed: 8611495
Wu J, Liu H, Yang H, Yu H, You D, Ma Y, Ye H, Lai R (2011) Proteomic analysis of skin defensive factors of tree frog Hyla simplex. J Proteome Res 10(9):4230–4240. https://doi.org/10.1021/pr200393t
doi: 10.1021/pr200393t
pubmed: 21740067
Wu Z, Kan SBJ, Lewis RD, Wittmann BJ, Arnold FH (2019) Machine learning-assisted directed protein evolution with combinatorial libraries. Proc Natl Acad Sci USA 116(18):8852–8858. https://doi.org/10.1073/pnas.1901979116
doi: 10.1073/pnas.1901979116
pubmed: 30979809
Yang JH, Wright SN, Hamblin M, McCloskey D, Alcantar MA, Schrübbers L, Lopatkin AJ, Satish S, Nili A, Palsson BO, Walker GC, Collins JJ (2019) A white-box machine learning approach for revealing antibiotic mechanisms of action. Cell 177(6):1649-1661.e9. https://doi.org/10.1016/j.cell.2019.04.016
doi: 10.1016/j.cell.2019.04.016
pubmed: 31080069
pmcid: 6545570
Yeaman MR, Yount NY (2003) Mechanisms of antimicrobial peptide action and resistance. Pharmacol Rev 55(1):27–55. https://doi.org/10.1124/pr.55.1.2
doi: 10.1124/pr.55.1.2
pubmed: 12615953
Yost RL, Ramphal R (1985) Ceftazidime review. Drug Intell Clin Pharm 19(7–8):509–513
doi: 10.1177/106002808501900701
Zasloff M (1987) Magainins, a class of antimicrobial peptides from Xenopus skin: isolation, characterization of two active forms, and partial cDNA sequence of a precursor. Proc Natl Acad Sci USA 84(15):5449–5453
doi: 10.1073/pnas.84.15.5449