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Home / Equine Research Bank / Biomacromolecules / Ultrashort cationic naphthalene-derived self-assembled pepti...
Biomacromolecules2014; 15(9); 3429-3439; doi: 10.1021/bm500981y

Ultrashort cationic naphthalene-derived self-assembled peptides as antimicrobial nanomaterials.

Abstract: Self-assembling dipeptides conjugated to naphthalene show considerable promise as nanomaterial structures, biomaterials, and drug delivery devices. Biomaterial infections are responsible for high rates of patient mortality and morbidity. The presence of biofilm bacteria, which thrive on implant surfaces, are a huge burden on healthcare budgets, as they are highly resistant to current therapeutic strategies. Ultrashort cationic self-assembled peptides represent a highly innovative and cost-effective strategy to form antibacterial nanomaterials. Lysine conjugated variants display the greatest potency with 2% w/v NapFFKK hydrogels significantly reducing the viable Staphylococcus epidermidis biofilm by 94%. Reducing the size of the R-group methylene chain on cationic moieties resulted in reduction of antibiofilm activity. The primary amine of the protruding R-group tail may not be as readily available to interact with negatively charged bacterial membranes. Cryo-SEM, FTIR, CD spectroscopy, and oscillatory rheology provided evidence of supramolecular hydrogel formation at physiological pH (pH 7.4). Cytotoxicity assays against murine fibroblast (NCTC 929) cell lines confirmed the gels possessed reduced cytotoxicity relative to bacterial cells, with limited hemolysis upon exposure to equine erythrocytes. The results presented in this paper highlight the significant potential of ultrashort cationic naphthalene peptides as future biomaterials.
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Publication Date: 2014-08-07 PubMed ID: 25068387DOI: 10.1021/bm500981yGoogle Scholar: Lookup
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  • Journal Article
  • Research Support
  • Non-U.S. Gov't

Summary

This research summary has been generated with artificial intelligence and may contain errors and omissions. Refer to the original study to confirm details provided. Submit correction.

The research article involves the formulation of self-assembling nanomaterials from dipeptides attached to naphthalene. These ultrashort cationic self-assembled peptides display considerable antibacterial properties, offering great potential for biomaterial and drug delivery applications.

Research Context

  • This research is anchored on the problem of high patient mortality and morbidity due to biomaterial infections. These infections primarily stem from biofilm bacteria, a type of bacteria that is resistant to most current therapeutic approaches and thrives on implant surfaces.
  • The paper introduces an innovatory and cost-effective strategy to combat this problem using ultrashort cationic self-assembled peptides. These peptides act as antimicrobial nanomaterials, with Lysine conjugated variants demonstrating the highest levels of antibacterial activity.

Research Processes

  • The researchers utilized a range of scientific methods to compile their findings. This included Cryo-SEM, FTIR, CD spectroscopy, and oscillatory rheology. All of these methods provided supportive evidence for the formation of supramolecular hydrogel at a physiological pH level of 7.4.
  • An important part of the research consists of cytotoxicity assays against murine fibroblast cell lines. According to results, the hydrogels exhibit lower cytotoxicity compared to bacterial cells, presenting only limited hemolysis when exposed to equine erythrocytes.

Key Findings

  • Through the study, it was found out that the use of 2% w/v NapFFKK hydrogels led to the reduction of viable Staphylococcus epidermidis biofilm by 94%, marking a significant breakthrough in the management of biofilm bacteria.
  • However, the reduction of the size of the R-group methylene chain on cationic moieties resulted in decreased antibiofilm activity. The researchers reasoned that the primary amine of the protruding R-group tail may not interact as easily with negatively charged bacterial membranes, thus explaining the drop in antibacterial activity.

Conclusion

  • The study concludes that ultrashort cationic naphthalene peptides have significant potential as future biomaterials, primarily due to their considerable antibacterial properties.
  • In addition to being used as antimicrobial nanomaterials, these peptides also show promise in drug delivery systems, as indicated by the research findings.

Cite This Article

APA
Laverty G, McCloskey AP, Gilmore BF, Jones DS, Zhou J, Xu B. (2014). Ultrashort cationic naphthalene-derived self-assembled peptides as antimicrobial nanomaterials. Biomacromolecules, 15(9), 3429-3439. https://doi.org/10.1021/bm500981y

Publication

Biomacromolecules
ISSN: 1526-4602
NlmUniqueID: 100892849
Country: United States
Language: English
Volume: 15
Issue: 9
Pages: 3429-3439

Researcher Affiliations

Laverty, Garry
  • School of Pharmacy, Queens University Belfast , 97 Lisburn Road, Belfast BT9 7BL, United Kingdom.
McCloskey, Alice P
    Gilmore, Brendan F
      Jones, David S
        Zhou, Jie
          Xu, Bing

            MeSH Terms

            • Animals
            • Anti-Infective Agents / chemical synthesis
            • Anti-Infective Agents / chemistry
            • Anti-Infective Agents / pharmacology
            • Biofilms / growth & development
            • Cell Line
            • Fibroblasts / cytology
            • Fibroblasts / metabolism
            • Hydrogels / chemical synthesis
            • Hydrogels / chemistry
            • Hydrogels / pharmacology
            • Materials Testing
            • Mice
            • Nanoparticles / chemistry
            • Peptides / chemical synthesis
            • Peptides / chemistry
            • Peptides / pharmacology
            • Staphylococcus epidermidis / physiology

            Citations

            This article has been cited 35 times.
            1. Attard ST, Aldilla VR, Kuppusamy R, Chen R, Black DS, Thordarson P, Willcox MDP, Kumar N. Tuning the Structure-Functional Properties Within Peptide-Mimicking Antimicrobial Hydrogels. Antibiotics (Basel) 2025 Nov 5;14(11).
              doi: 10.3390/antibiotics14111118pubmed: 41301613google scholar: lookup
            2. Bellan R, Attia D, van Genderen MHP, Dankers PYW. Hybrid pH Responsive Supramolecular Polymers Through the Combination of the Ureido-Pyrimidinone Motif with β-Sheet Peptide Sequences. Chemistry 2025 Jun 12;31(33):e202500429.
              doi: 10.1002/chem.202500429pubmed: 40370199google scholar: lookup
            3. Moore JV, Cross ER, An Y, Pentlavalli S, Coulter SM, Sun H, Laverty G. Impact of counterion and salt form on the properties of long-acting injectable peptide hydrogels for drug delivery. Faraday Discuss 2025 Aug 28;260(0):215-234.
              doi: 10.1039/d4fd00194jpubmed: 40365687google scholar: lookup
            4. Levin A, Hakala TA, Schnaider L, Bernardes GJL, Gazit E, Knowles TPJ. Biomimetic peptide self-assembly for functional materials. Nat Rev Chem 2020 Sep 15;4(11):615-634.
              doi: 10.1038/s41570-020-0215-ypubmed: 39650726google scholar: lookup
            5. Coulter SM, Pentlavalli S, An Y, Vora LK, Cross ER, Moore JV, Sun H, Schweins R, McCarthy HO, Laverty G. In Situ Forming, Enzyme-Responsive Peptoid-Peptide Hydrogels: An Advanced Long-Acting Injectable Drug Delivery System. J Am Chem Soc 2024 Aug 7;146(31):21401-21416.
              doi: 10.1021/jacs.4c03751pubmed: 38922296google scholar: lookup
            6. Özbek N, Vilarrocha EL, Jover BV, Ventura EF, Escuder B. Lysine-based non-cytotoxic ultrashort self-assembling peptides with antimicrobial activity. RSC Adv 2024 May 2;14(21):15120-15128.
              doi: 10.1039/d3ra08883apubmed: 38720978google scholar: lookup
            7. Ligorio C, Mata A. Synthetic extracellular matrices with function-encoding peptides. Nat Rev Bioeng 2023 Apr 25;:1-19.
              doi: 10.1038/s44222-023-00055-3pubmed: 37359773google scholar: lookup
            8. Yang S, Wang M, Wang T, Sun M, Huang H, Shi X, Duan S, Wu Y, Zhu J, Liu F. Self-assembled short peptides: Recent advances and strategies for potential pharmaceutical applications. Mater Today Bio 2023 Jun;20:100644.
              doi: 10.1016/j.mtbio.2023.100644pubmed: 37214549google scholar: lookup
            9. Sedighi M, Shrestha N, Mahmoudi Z, Khademi Z, Ghasempour A, Dehghan H, Talebi SF, Toolabi M, Préat V, Chen B, Guo X, Shahbazi MA. Multifunctional Self-Assembled Peptide Hydrogels for Biomedical Applications. Polymers (Basel) 2023 Feb 25;15(5).
              doi: 10.3390/polym15051160pubmed: 36904404google scholar: lookup
            10. Coulter SM, Pentlavalli S, Vora LK, An Y, Cross ER, Peng K, McAulay K, Schweins R, Donnelly RF, McCarthy HO, Laverty G. Enzyme-Triggered l-α/d-Peptide Hydrogels as a Long-Acting Injectable Platform for Systemic Delivery of HIV/AIDS Drugs. Adv Healthc Mater 2023 Jul;12(18):e2203198.
              doi: 10.1002/adhm.202203198pubmed: 36880399google scholar: lookup
            11. Hamley IW. Self-Assembly, Bioactivity, and Nanomaterials Applications of Peptide Conjugates with Bulky Aromatic Terminal Groups. ACS Appl Bio Mater 2023 Feb 20;6(2):384-409.
              doi: 10.1021/acsabm.2c01041pubmed: 36735801google scholar: lookup
            12. Aldilla VR, Chen R, Kuppusamy R, Chakraborty S, Willcox MDP, Black DS, Thordarson P, Martin AD, Kumar N. Hydrogels with intrinsic antibacterial activity prepared from naphthyl anthranilamide (NaA) capped peptide mimics. Sci Rep 2022 Dec 23;12(1):22259.
              doi: 10.1038/s41598-022-26426-1pubmed: 36564414google scholar: lookup
            13. Askoura M, Yousef N, Mansour B, Yehia FAA. Antibiofilm and staphyloxanthin inhibitory potential of terbinafine against Staphylococcus aureus: in vitro and in vivo studies. Ann Clin Microbiol Antimicrob 2022 May 30;21(1):21.
              doi: 10.1186/s12941-022-00513-7pubmed: 35637481google scholar: lookup
            14. Chakraborty S, Chatterjee R, Chakravortty D. Evolving and assembling to pierce through: Evolutionary and structural aspects of antimicrobial peptides. Comput Struct Biotechnol J 2022;20:2247-2258.
              doi: 10.1016/j.csbj.2022.05.002pubmed: 35615024google scholar: lookup
            15. Thushara N, Darshani T, Samarakoon SR, Perera IC, Fronczek FR, Sameera WMC, Perera T. Synthesis, characterization and biological evaluation of dipicolylamine sulfonamide derivatized platinum complexes as potential anticancer agents. RSC Adv 2021 May 13;11(29):17658-17668.
              doi: 10.1039/d1ra00842kpubmed: 35480201google scholar: lookup
            16. Guan T, Li J, Chen C, Liu Y. Self-Assembling Peptide-Based Hydrogels for Wound Tissue Repair. Adv Sci (Weinh) 2022 Apr;9(10):e2104165.
              doi: 10.1002/advs.202104165pubmed: 35142093google scholar: lookup
            17. Wang L, Liu L, Zhou X. Bacitracin-Ag Nanoclusters as a Novel Antibacterial Agent Combats Shigella flexneri by Disrupting Cell Membrane and Inhibiting Biofilm Formation. Nanomaterials (Basel) 2021 Nov 1;11(11).
              doi: 10.3390/nano11112928pubmed: 34835692google scholar: lookup
            18. Afami ME, El Karim I, About I, Krasnodembskaya AD, Laverty G, Lundy FT. Multicomponent Peptide Hydrogels as an Innovative Platform for Cell-Based Tissue Engineering in the Dental Pulp. Pharmaceutics 2021 Sep 28;13(10).
              doi: 10.3390/pharmaceutics13101575pubmed: 34683868google scholar: lookup
            19. Cross ER, Coulter SM, Pentlavalli S, Laverty G. Unravelling the antimicrobial activity of peptide hydrogel systems: current and future perspectives. Soft Matter 2021 Sep 15;17(35):8001-8021.
              doi: 10.1039/d1sm00839kpubmed: 34525154google scholar: lookup
            20. Yang Z, He S, Wu H, Yin T, Wang L, Shan A. Nanostructured Antimicrobial Peptides: Crucial Steps of Overcoming the Bottleneck for Clinics. Front Microbiol 2021;12:710199.
              doi: 10.3389/fmicb.2021.710199pubmed: 34475862google scholar: lookup
            21. d'Orlyé F, Trapiella-Alfonso L, Lescot C, Pinvidic M, Doan BT, Varenne A. Synthesis, Characterization and Evaluation of Peptide Nanostructures for Biomedical Applications. Molecules 2021 Jul 29;26(15).
              doi: 10.3390/molecules26154587pubmed: 34361740google scholar: lookup
            22. Zhou Y, Qiu P, Yao D, Song Y, Zhu Y, Pan H, Wu J, Zhang J. A crosslinked colloidal network of peptide/nucleic base amphiphiles for targeted cancer cell encapsulation. Chem Sci 2021 Jul 28;12(29):10063-10069.
              doi: 10.1039/d1sc02995apubmed: 34349970google scholar: lookup
            23. Afami ME, El Karim I, About I, Coulter SM, Laverty G, Lundy FT. Ultrashort Peptide Hydrogels Display Antimicrobial Activity and Enhance Angiogenic Growth Factor Release by Dental Pulp Stem/Stromal Cells. Materials (Basel) 2021 Apr 27;14(9).
              doi: 10.3390/ma14092237pubmed: 33925337google scholar: lookup
            24. Thota CK, Mikolajczak DJ, Roth C, Koksch B. Enhancing Antimicrobial Peptide Potency through Multivalent Presentation on Coiled-Coil Nanofibrils. ACS Med Chem Lett 2021 Jan 14;12(1):67-73.
              doi: 10.1021/acsmedchemlett.0c00425pubmed: 33488966google scholar: lookup
            25. De Zoysa GH, Wang K, Lu J, Hemar Y, Sarojini V. Covalently Immobilized Battacin Lipopeptide Gels with Activity against Bacterial Biofilms. Molecules 2020 Dec 15;25(24).
              doi: 10.3390/molecules25245945pubmed: 33334031google scholar: lookup
            26. Alnufaie R, Alsup N, Kc HR, Newman M, Whitt J, Chambers SA, Gilmore D, Alam MA. Design and synthesis of 4-[4-formyl-3-(2-naphthyl)pyrazol-1-yl]benzoic acid derivatives as potent growth inhibitors of drug-resistant Staphylococcus aureus. J Antibiot (Tokyo) 2020 Dec;73(12):818-827.
              doi: 10.1038/s41429-020-0341-2pubmed: 32601342google scholar: lookup
            27. Aldilla VR, Chen R, Martin AD, Marjo CE, Rich AM, Black DS, Thordarson P, Kumar N. Anthranilamide-based Short Peptides Self-Assembled Hydrogels as Antibacterial Agents. Sci Rep 2020 Jan 21;10(1):770.
              doi: 10.1038/s41598-019-57342-6pubmed: 31964927google scholar: lookup
            28. Falcone N, Shao T, Rashid R, Kraatz HB. Enzyme Entrapment in Amphiphilic Myristyl-Phenylalanine Hydrogels. Molecules 2019 Aug 8;24(16).
              doi: 10.3390/molecules24162884pubmed: 31398913google scholar: lookup
            29. Lombardi L, Falanga A, Del Genio V, Galdiero S. A New Hope: Self-Assembling Peptides with Antimicrobial Activity. Pharmaceutics 2019 Apr 4;11(4).
              doi: 10.3390/pharmaceutics11040166pubmed: 30987353google scholar: lookup
            30. Albadr AA, Coulter SM, Porter SL, Thakur RRS, Laverty G. Ultrashort Self-Assembling Peptide Hydrogel for the Treatment of Fungal Infections. Gels 2018 May 22;4(2).
              doi: 10.3390/gels4020048pubmed: 30674824google scholar: lookup
            31. Boto A, Pérez de la Lastra JM, González CC. The Road from Host-Defense Peptides to a New Generation of Antimicrobial Drugs. Molecules 2018 Feb 1;23(2).
              doi: 10.3390/molecules23020311pubmed: 29389911google scholar: lookup
            32. Schnaider L, Brahmachari S, Schmidt NW, Mensa B, Shaham-Niv S, Bychenko D, Adler-Abramovich L, Shimon LJW, Kolusheva S, DeGrado WF, Gazit E. Self-assembling dipeptide antibacterial nanostructures with membrane disrupting activity. Nat Commun 2017 Nov 8;8(1):1365.
              doi: 10.1038/s41467-017-01447-xpubmed: 29118336google scholar: lookup
            33. Du X, Zhou J, Shi J, Xu B. Supramolecular Hydrogelators and Hydrogels: From Soft Matter to Molecular Biomaterials. Chem Rev 2015 Dec 23;115(24):13165-307.
              doi: 10.1021/acs.chemrev.5b00299pubmed: 26646318google scholar: lookup
            34. Wang G, Mishra B, Lau K, Lushnikova T, Golla R, Wang X. Antimicrobial peptides in 2014. Pharmaceuticals (Basel) 2015 Mar 23;8(1):123-50.
              doi: 10.3390/ph8010123pubmed: 25806720google scholar: lookup
            35. McCloskey AP, Gilmore BF, Laverty G. Evolution of antimicrobial peptides to self-assembled peptides for biomaterial applications. Pathogens 2014 Oct 3;3(4):791-821.
              doi: 10.3390/pathogens3040791pubmed: 25436505google scholar: lookup
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