دورية أكاديمية
Antimicrobial Evaluation of Two Polycyclic Polyprenylated Acylphloroglucinol Compounds: PPAP23 and PPAP53.
العنوان: | Antimicrobial Evaluation of Two Polycyclic Polyprenylated Acylphloroglucinol Compounds: PPAP23 and PPAP53. |
---|---|
المؤلفون: | Ammanath AV; Microbial Genetics, Interfaculty Institute of Microbiology and Infection Medicine Tübingen (IMIT), University of Tübingen, 72076 Tübingen, Germany., Matsuo M; Microbial Genetics, Interfaculty Institute of Microbiology and Infection Medicine Tübingen (IMIT), University of Tübingen, 72076 Tübingen, Germany., Wang H; Microbial Genetics, Interfaculty Institute of Microbiology and Infection Medicine Tübingen (IMIT), University of Tübingen, 72076 Tübingen, Germany., Kraus F; Organic Chemistry I, Faculty of Chemistry and Food Chemistry, Technical University Dresden, 01062 Dresden, Germany., Bleisch A; Organic Chemistry I, Faculty of Chemistry and Food Chemistry, Technical University Dresden, 01062 Dresden, Germany., Peslalz P; Organic Chemistry I, Faculty of Chemistry and Food Chemistry, Technical University Dresden, 01062 Dresden, Germany., Mohammad M; Department of Rheumatology and Inflammation Research, Institute of Medicine, Sahlgrenska Academy, University of Gothenburg, 40530 Gothenburg, Sweden., Deshmukh M; Department of Rheumatology and Inflammation Research, Institute of Medicine, Sahlgrenska Academy, University of Gothenburg, 40530 Gothenburg, Sweden., Grießhammer A; Interfakultäres Institut für Mikrobiologie und Infektionsmedizin (IMIT), University of Tübingen, 72076 Tübingen, Germany.; Excellence Cluster 2124 'Controlling Microbes to Fight Infections' (CMFI), University of Tübingen, 72076 Tübingen, Germany., Purkayastha M; Microbial Genetics, Interfaculty Institute of Microbiology and Infection Medicine Tübingen (IMIT), University of Tübingen, 72076 Tübingen, Germany., Vorbach A; Microbial Bioactive Compounds, Interfaculty Institute of Microbiology and Infection Medicine Tübingen (IMIT), University of Tübingen, 72076 Tübingen, Germany., Macek B; Excellence Cluster 2124 'Controlling Microbes to Fight Infections' (CMFI), University of Tübingen, 72076 Tübingen, Germany.; Quantitative Proteomics, Proteome Center Tübingen, Interfaculty Institute for Cell Biology, University of Tübingen, 72076 Tübingen, Germany., Brötz-Oesterhelt H; Excellence Cluster 2124 'Controlling Microbes to Fight Infections' (CMFI), University of Tübingen, 72076 Tübingen, Germany.; Microbial Bioactive Compounds, Interfaculty Institute of Microbiology and Infection Medicine Tübingen (IMIT), University of Tübingen, 72076 Tübingen, Germany., Maier L; Interfakultäres Institut für Mikrobiologie und Infektionsmedizin (IMIT), University of Tübingen, 72076 Tübingen, Germany.; Excellence Cluster 2124 'Controlling Microbes to Fight Infections' (CMFI), University of Tübingen, 72076 Tübingen, Germany., Kretschmer D; Interfakultäres Institut für Mikrobiologie und Infektionsmedizin (IMIT), University of Tübingen, 72076 Tübingen, Germany.; Excellence Cluster 2124 'Controlling Microbes to Fight Infections' (CMFI), University of Tübingen, 72076 Tübingen, Germany., Peschel A; Interfakultäres Institut für Mikrobiologie und Infektionsmedizin (IMIT), University of Tübingen, 72076 Tübingen, Germany.; Excellence Cluster 2124 'Controlling Microbes to Fight Infections' (CMFI), University of Tübingen, 72076 Tübingen, Germany., Jin T; Department of Rheumatology and Inflammation Research, Institute of Medicine, Sahlgrenska Academy, University of Gothenburg, 40530 Gothenburg, Sweden., Plietker B; Organic Chemistry I, Faculty of Chemistry and Food Chemistry, Technical University Dresden, 01062 Dresden, Germany., Götz F; Microbial Genetics, Interfaculty Institute of Microbiology and Infection Medicine Tübingen (IMIT), University of Tübingen, 72076 Tübingen, Germany.; Excellence Cluster 2124 'Controlling Microbes to Fight Infections' (CMFI), University of Tübingen, 72076 Tübingen, Germany. |
المصدر: | International journal of molecular sciences [Int J Mol Sci] 2024 Jul 23; Vol. 25 (15). Date of Electronic Publication: 2024 Jul 23. |
نوع المنشور: | Journal Article |
اللغة: | English |
بيانات الدورية: | Publisher: MDPI Country of Publication: Switzerland NLM ID: 101092791 Publication Model: Electronic Cited Medium: Internet ISSN: 1422-0067 (Electronic) Linking ISSN: 14220067 NLM ISO Abbreviation: Int J Mol Sci Subsets: MEDLINE |
أسماء مطبوعة: | Original Publication: Basel, Switzerland : MDPI, [2000- |
مواضيع طبية MeSH: | Ketones*/chemistry , Ketones*/pharmacology , Methicillin-Resistant Staphylococcus aureus*/drug effects , Spiro Compounds*/chemistry , Spiro Compounds*/pharmacology, Animals ; Humans ; Mice ; Anti-Bacterial Agents/pharmacology ; Anti-Bacterial Agents/chemistry ; Enterococcus faecium/drug effects ; Larva/drug effects ; Microbial Sensitivity Tests ; Molecular Docking Simulation ; Moths/drug effects ; Staphylococcal Infections/drug therapy |
مستخلص: | Polycyclic polyprenylated acylphloroglucinols (PPAPs) comprise a large group of compounds of mostly plant origin. The best-known compound is hyperforin from St. John's wort with its antidepressant, antitumor and antimicrobial properties. The chemical synthesis of PPAP variants allows the generation of compounds with improved activity and compatibility. Here, we studied the antimicrobial activity of two synthetic PPAP-derivatives, the water-insoluble PPAP23 and the water-soluble sodium salt PPAP53. In vitro, both compounds exhibited good activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium . Both compounds had no adverse effects on Galleria mellonella wax moth larvae. However, they were unable to protect the larvae from infection with S. aureus because components of the larval coelom neutralized the antimicrobial activity; a similar effect was also seen with serum albumin. In silico docking studies with PPAP53 revealed that it binds to the F1 pocket of human serum albumin with a binding energy of -7.5 kcal/mol. In an infection model of septic arthritis, PPAP23 decreased the formation of abscesses and S. aureus load in kidneys; in a mouse skin abscess model, topical treatment with PPAP53 reduced S. aureus counts. Both PPAPs were active against anaerobic Gram-positive gut bacteria such as neurotransmitter-producing Clostridium , Enterococcus or Ruminococcus species. Based on these results, we foresee possible applications in the decolonization of pathogens. |
References: | Nat Protoc. 2008;3(2):163-75. (PMID: 18274517) J Am Chem Soc. 2014 Mar 12;136(10):4026-30. (PMID: 24579977) Proc Natl Acad Sci U S A. 2019 Jun 25;116(26):12672-12677. (PMID: 31182571) Chem Rev. 2006 Sep;106(9):3963-86. (PMID: 16967926) J Antimicrob Chemother. 2006 Apr;57(4):589-608. (PMID: 16507559) Science. 2019 Jun 14;364(6445):. (PMID: 31196984) Antimicrob Agents Chemother. 2016 Mar 25;60(4):2391-401. (PMID: 26856834) J Clin Microbiol. 2012 Apr;50(4):1153-7. (PMID: 22238439) J Microbiol Methods. 2001 Mar 1;44(2):121-9. (PMID: 11165341) Scand J Clin Lab Invest. 1995 Feb;55(1):35-45. (PMID: 7624735) Dermatol Reports. 2021 Aug 05;14(2):9289. (PMID: 35795839) Chem Rev. 2018 Apr 11;118(7):3508-3558. (PMID: 29461053) Gut Microbes. 2021 Jan-Dec;13(1):1922241. (PMID: 34196581) Nat Microbiol. 2017 Jan 23;2:16257. (PMID: 28112716) J Antimicrob Chemother. 2023 Aug 2;78(8):2061-2065. (PMID: 37358399) Cell. 2019 May 16;177(5):1217-1231.e18. (PMID: 31006530) PLoS One. 2017 Mar 6;12(3):e0173492. (PMID: 28264025) Lancet Neurol. 2020 Feb;19(2):179-194. (PMID: 31753762) Cell Rep. 2018 Jan 9;22(2):535-545. (PMID: 29320746) J Med Chem. 2023 Nov 23;66(22):15073-15083. (PMID: 37822271) Phytochemistry. 2006 Oct;67(20):2201-7. (PMID: 16973193) Bioinformatics. 2011 Jul 1;27(13):1806-13. (PMID: 21593135) Nat Prod Bioprospect. 2021 Dec;11(6):629-641. (PMID: 34586597) J Drugs Dermatol. 2021 Feb 1;20(2):134-142. (PMID: 33538559) Front Microbiol. 2019 Jan 22;10:14. (PMID: 30728811) Ann Clin Biochem. 1990 May;27 ( Pt 3):208-12. (PMID: 2200332) J Biol Chem. 2000 Dec 8;275(49):38731-8. (PMID: 10940303) Nat Rev Microbiol. 2016 Oct;14(10):609-20. (PMID: 27573580) J Pharm Pharmacol. 2001 May;53(5):583-600. (PMID: 11370698) Angew Chem Int Ed Engl. 2012 May 7;51(19):4536-61. (PMID: 22461155) J Mol Biol. 2005 Oct 14;353(1):38-52. (PMID: 16169013) J Infect Dis. 2015 Oct 15;212(8):1308-16. (PMID: 25838268) J Nat Prod. 2013 Sep 27;76(9):1819-23. (PMID: 23981190) Angew Chem Int Ed Engl. 2017 Dec 11;56(50):15852-15856. (PMID: 28985019) Nat Chem. 2011 Oct 16;3(12):938-42. (PMID: 22109273) Chemistry. 2024 Jun 11;:e202401955. (PMID: 38860572) Cell Host Microbe. 2014 Oct 8;16(4):495-503. (PMID: 25263219) Chemistry. 2015 Feb 9;21(7):3053-61. (PMID: 25537962) Mol Pharm. 2020 Mar 2;17(3):810-816. (PMID: 31967843) J Pharm Biomed Anal. 2022 Mar 20;211:114593. (PMID: 35086032) Life Sci. 1998;63(6):499-510. (PMID: 9718074) J Infect Dis. 2017 Dec 27;217(1):147-157. (PMID: 28968861) Access Microbiol. 2020 Jun 15;2(8):acmi000137. (PMID: 32974599) Cell Physiol Biochem. 2020 Sep 16;54(5):888-898. (PMID: 32930525) J Comput Chem. 2010 Jan 30;31(2):455-61. (PMID: 19499576) Virulence. 2016 Apr 2;7(3):214-29. (PMID: 26730990) Biomolecules. 2021 Jul 23;11(8):. (PMID: 34439760) J Med Chem. 2023 Nov 23;66(22):15061-15072. (PMID: 37922400) Asian Pac J Trop Biomed. 2012 Jun;2(6):496-502. (PMID: 23569958) Dokl Akad Nauk SSSR. 1976 Jan 1;226(1):88-90. (PMID: 1248360) Eur J Pharm Biopharm. 2018 May;126:115-122. (PMID: 28870756) BMC Struct Biol. 2003 Jul 7;3:6. (PMID: 12846933) Sci Rep. 2019 Nov 13;9(1):16663. (PMID: 31723175) Medicine (Baltimore). 2019 May;98(19):e15664. (PMID: 31083269) J Nat Prod. 2002 Apr;65(4):433-8. (PMID: 11975475) Expert Opin Drug Saf. 2021 Jun;20(6):677-683. (PMID: 33726585) Nat Protoc. 2024 Mar;19(3):668-699. (PMID: 38092943) Antimicrob Agents Chemother. 1985 Apr;27(4):495-8. (PMID: 3923922) |
معلومات مُعتمدة: | GO 371/18-1 Deutsche Forschungsgemeinschaft; AntibioPPAP Ministry for Science, Research and the Arts of Baden-Wuerttemberg (MWK) |
فهرسة مساهمة: | Keywords: PPAP; albumin; antimicrobial activity; gastrointestinal anaerobes; larvae; mouse septic arthroses |
المشرفين على المادة: | 0 (Anti-Bacterial Agents) 0 (Ketones) 0 (PPAP53) 0 (Spiro Compounds) |
تواريخ الأحداث: | Date Created: 20240810 Date Completed: 20240810 Latest Revision: 20240812 |
رمز التحديث: | 20240813 |
مُعرف محوري في PubMed: | PMC11312133 |
DOI: | 10.3390/ijms25158023 |
PMID: | 39125595 |
قاعدة البيانات: | MEDLINE |
تدمد: | 1422-0067 |
---|---|
DOI: | 10.3390/ijms25158023 |