دورية أكاديمية
Stapled β-Hairpin Antimicrobial Peptides with Improved Stability and Activity against Drug-Resistant Gram-Negative Bacteria.
العنوان: | Stapled β-Hairpin Antimicrobial Peptides with Improved Stability and Activity against Drug-Resistant Gram-Negative Bacteria. |
---|---|
المؤلفون: | Selvarajan V; Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore., Tram NDT; Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore., Xu J; Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore., Ngen STY; Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore., Koh JJ; Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore., Teo JWP; Department of Laboratory Medicine, Microbiology Unit, National University Hospital, Singapore 119074, Singapore., Yuen TY; Agency for Science, Technology and Research (A*STAR), Singapore 138665, Singapore., Ee PLR; Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore. |
المصدر: | Journal of medicinal chemistry [J Med Chem] 2023 Jul 13; Vol. 66 (13), pp. 8498-8509. Date of Electronic Publication: 2023 Jun 25. |
نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
اللغة: | English |
بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 9716531 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-4804 (Electronic) Linking ISSN: 00222623 NLM ISO Abbreviation: J Med Chem Subsets: MEDLINE |
أسماء مطبوعة: | Publication: Washington Dc : American Chemical Society Original Publication: [Easton, Pa.] : American Chemical Society, [c1963- |
مواضيع طبية MeSH: | Antimicrobial Cationic Peptides*/chemistry , Antimicrobial Peptides*, Gram-Negative Bacteria ; Bacteria ; Microbial Sensitivity Tests ; Hydrocarbons/chemistry ; Anti-Bacterial Agents/chemistry |
مستخلص: | Different stapling techniques have been used recently to address the subpar performance of antimicrobial peptides (AMPs) in clinical trials with ample focus on α-helical AMPs. In comparison, a systematic evaluation of such strategies on β-hairpin AMPs is lacking. Herein, we report the design, synthesis, and evaluation of a library of all-hydrocarbon-stapled β-hairpin AMPs with variation in key parameters intended as potent therapeutics against drug-resistant pathogens. We observed an interesting interplay between the activity, stability, and structural strength. Single-stapled peptides with a 6-carbon staple at peptide termini such as 5(c 6 ) displayed the most potent activity against colistin-resistant clinical isolates. Using imaging techniques, we observed translocation of 5(c 6 ) across bacterial membranes without causing extensive damage. Overall, we have engineered novel all-hydrocarbon-stapled β-hairpin AMPs with structural and functional proficiency that can effectively combat resistant pathogens, with findings from this study a point of reference for future interests in developing novel β-hairpin AMPs. |
References: | Acta Biomater. 2017 Jul 15;57:103-114. (PMID: 28457962) Acta Biochim Biophys Acad Sci Hung. 1976;11(4):287-94. (PMID: 1026004) Bioorg Med Chem. 2018 Jun 1;26(10):2700-2707. (PMID: 28720325) Front Chem. 2014 Aug 08;2:62. (PMID: 25152873) Chem Soc Rev. 2015 Jan 7;44(1):91-102. (PMID: 25199043) Nat Rev Microbiol. 2019 Jan;17(1):3. (PMID: 30467331) Acta Biomater. 2015 Dec;28:99-108. (PMID: 26380930) ACS Chem Biol. 2018 Aug 17;13(8):2027-2032. (PMID: 30005156) Bioorg Med Chem. 2018 Mar 15;26(6):1189-1196. (PMID: 29275987) J Pept Sci. 2003 Aug;9(8):471-501. (PMID: 12952390) Nat Protoc. 2008;3(2):163-75. (PMID: 18274517) Biochim Biophys Acta. 2012 Jan;1823(1):40-8. (PMID: 21925212) Infect Immun. 2012 Feb;80(2):483-92. (PMID: 22144482) Oncogene. 2015 Nov 12;34(46):5685-98. (PMID: 25798838) Microorganisms. 2021 Jun 08;9(6):. (PMID: 34201398) Chem Sci. 2016 Aug 1;7(8):5212-5218. (PMID: 29449932) Lancet Infect Dis. 2006 Sep;6(9):589-601. (PMID: 16931410) Res Microbiol. 2009 Nov;160(9):652-9. (PMID: 19744556) Mini Rev Med Chem. 2002 Oct;2(5):463-73. (PMID: 12370047) Curr Pharm Des. 2010;16(28):3185-203. (PMID: 20687878) J Pept Sci. 1995 Jul-Aug;1(4):274-82. (PMID: 9223005) FEMS Microbiol Lett. 1992 Oct 1;76(1-2):51-6. (PMID: 1427004) Appl Environ Microbiol. 1997 Jun;63(6):2421-31. (PMID: 9172364) Sci Rep. 2020 Mar 10;10(1):4408. (PMID: 32157139) Biomaterials. 2014 Feb;35(6):2032-8. (PMID: 24314557) Chem Commun (Camb). 2013 Oct 14;49(80):9131-3. (PMID: 24005767) J Clin Invest. 1989 Aug;84(2):553-61. (PMID: 2668334) Acta Biomater. 2021 Nov;135:214-224. (PMID: 34506975) Front Chem. 2019 Feb 04;7:43. (PMID: 30778385) Biochemistry. 1996 Oct 29;35(43):13723-8. (PMID: 8901513) Curr Infect Dis Rep. 2017 Sep 11;19(11):38. (PMID: 28895051) Antimicrob Agents Chemother. 2000 Mar;44(3):602-7. (PMID: 10681325) Sci Rep. 2016 Nov 22;6:37639. (PMID: 27874065) Mol Membr Biol. 2007 Sep-Dec;24(5-6):395-406. (PMID: 17710644) Nat Protoc. 2011 Jun;6(6):761-71. (PMID: 21637196) Amino Acids. 2012 Nov;43(5):2047-58. (PMID: 22526241) Nanoscale. 2018 Dec 20;11(1):266-275. (PMID: 30534763) Nat Rev Urol. 2015 Oct;12(10):570-84. (PMID: 26334085) Nat Biotechnol. 2019 Oct;37(10):1186-1197. (PMID: 31427820) Org Biomol Chem. 2018 Jan 17;16(3):389-392. (PMID: 29271460) Microbiol Mol Biol Rev. 2012 Jun;76(2):311-30. (PMID: 22688815) Nat Chem. 2011 Jun 23;3(7):509-24. (PMID: 21697871) Eur J Med Chem. 2015 Apr 13;94:471-9. (PMID: 25109255) Protein J. 2018 Feb;37(1):2-12. (PMID: 29330644) Biochemistry. 1996 Aug 6;35(31):10041-50. (PMID: 8756466) Res Microbiol. 2009 Nov;160(9):629-36. (PMID: 19781640) Bioorg Med Chem Lett. 2013 Dec 15;23(24):6717-20. (PMID: 24211019) Arch Pharm Res. 2017 Jun;40(6):713-719. (PMID: 28547390) Chem Soc Rev. 2021 Apr 26;50(8):4932-4973. (PMID: 33710195) Biochim Biophys Acta. 2013 Nov;1828(11):2479-86. (PMID: 23806649) Biochemistry. 2010 May 18;49(19):4076-84. (PMID: 20387900) Curr Protoc Chem Biol. 2011 Sep 1;3(3):99-117. (PMID: 23801563) Arch Pharm Res. 2017 Dec;40(12):1414-1419. (PMID: 29075946) Bioorg Med Chem Lett. 2015 Sep 15;25(18):4016-9. (PMID: 26235946) Molecules. 2020 Jul 03;25(13):. (PMID: 32635310) Int J Mol Sci. 2021 Oct 16;22(20):. (PMID: 34681833) Nat Commun. 2017 Dec 22;8(1):2263. (PMID: 29273729) Antibiotics (Basel). 2020 Jan 13;9(1):. (PMID: 31941022) J Appl Microbiol. 2000 Feb;88(2):213-9. (PMID: 10735988) J Am Chem Soc. 2004 Oct 6;126(39):12252-3. (PMID: 15453743) Pharmacol Rev. 2003 Mar;55(1):27-55. (PMID: 12615953) Microbiol Immunol. 2010 Aug;54(8):452-9. (PMID: 20646209) ACS Chem Biol. 2016 Aug 19;11(8):2375-82. (PMID: 27336832) J Antimicrob Chemother. 2016 Aug;71(8):2181-91. (PMID: 27118774) J Am Chem Soc. 2009 Jun 10;131(22):7609-17. (PMID: 19445503) J Antimicrob Chemother. 2014 Jan;69(1):121-32. (PMID: 23946320) Angew Chem Int Ed Engl. 1998 Dec 17;37(23):3281-3284. (PMID: 29711420) J Bacteriol. 2000 Jul;182(14):4077-86. (PMID: 10869088) ACS Appl Mater Interfaces. 2019 Aug 14;11(32):28681-28689. (PMID: 31328913) Nat Rev Microbiol. 2021 Dec;19(12):786-797. (PMID: 34183822) Acc Chem Res. 2008 Oct;41(10):1331-42. (PMID: 18636716) Biochim Biophys Acta. 2009 Aug;1788(8):1687-92. (PMID: 18952049) |
المشرفين على المادة: | 0 (Antimicrobial Cationic Peptides) 0 (Antimicrobial Peptides) 0 (Hydrocarbons) 0 (Anti-Bacterial Agents) |
تواريخ الأحداث: | Date Created: 20230626 Date Completed: 20230714 Latest Revision: 20230719 |
رمز التحديث: | 20231215 |
مُعرف محوري في PubMed: | PMC10350921 |
DOI: | 10.1021/acs.jmedchem.3c00140 |
PMID: | 37357499 |
قاعدة البيانات: | MEDLINE |
تدمد: | 1520-4804 |
---|---|
DOI: | 10.1021/acs.jmedchem.3c00140 |