دورية أكاديمية
أعرض في EDS

Development of New Antimicrobial Oleanonic Acid Polyamine Conjugates.

التفاصيل البيبلوغرافية
العنوان: Development of New Antimicrobial Oleanonic Acid Polyamine Conjugates.
المؤلفون: Khusnutdinova EF; Ufa Institute of Chemistry UFRC RAS, 71 pr. Oktyabrya, 450054 Ufa, Russia.; Aix Marseille Univ, INSERM, SSA, MCT, 13385 Marseille, France., Sinou V; Aix Marseille Univ, INSERM, SSA, MCT, 13385 Marseille, France., Babkov DA; Scientific Center for Innovative Drugs, Volgograd State Medical University, Novorossiyskaya st. 39, 400087 Volgograd, Russia., Kazakova O; Ufa Institute of Chemistry UFRC RAS, 71 pr. Oktyabrya, 450054 Ufa, Russia., Brunel JM; Aix Marseille Univ, INSERM, SSA, MCT, 13385 Marseille, France.
المصدر: Antibiotics (Basel, Switzerland) [Antibiotics (Basel)] 2022 Jan 12; Vol. 11 (1). Date of Electronic Publication: 2022 Jan 12.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: MDPI AG Country of Publication: Switzerland NLM ID: 101637404 Publication Model: Electronic Cited Medium: Print ISSN: 2079-6382 (Print) Linking ISSN: 20796382 NLM ISO Abbreviation: Antibiotics (Basel) Subsets: PubMed not MEDLINE
أسماء مطبوعة: Original Publication: Basel, Switzerland : MDPI AG, 2012-
مستخلص: A series of oleanolic acid derivatives holding oxo- or 3- N -polyamino-3-deoxy-substituents at C3 as well as carboxamide function at C17 with different long chain polyamines have been synthesized and evaluated for antimicrobial activities. Almost all series presented good to moderate activity against Gram-positive S. aureus , S. faecalis and B. cereus bacteria with minimum inhibitory concentration (MIC) values from 3.125 to 200 µg/mL. Moreover, compounds possess important antimicrobial activities against Gram-negative E. coli , P. aeruginosa , S. enterica , and EA289 bacteria with MICs ranging from 6.25 to 200 µg/mL. The testing of ability to restore antibiotic activity of doxycycline and erythromycin at a 2 µg/mL concentration in a synergistic assay showed that oleanonic acid conjugate with spermine spacered through propargylamide led to a moderate improvement in terms of antimicrobial activities of the different selected combinations against both P. aeruginosa and E. coli . The study of mechanism of action of the lead conjugate 2i presenting a N -methyl norspermidine moiety showed the effect of disruption of the outer bacterial membrane of P. aeruginosa PA01 cells. Computational ADMET profiling renders this compound as a suitable starting point for pharmacokinetic optimization. These results give confidence to the successful outcome of bioconjugation of polyamines and oleanane-type triterpenoids in the development of antimicrobial agents.
References: Bioorg Med Chem. 2013 Jan 15;21(2):425-35. (PMID: 23245801)
Molecules. 2015 Nov 19;20(11):20614-41. (PMID: 26610440)
ACS Med Chem Lett. 2018 Apr 19;9(6):522-527. (PMID: 29937976)
Front Microbiol. 2019 Aug 13;10:1771. (PMID: 31456758)
Bioorg Med Chem Lett. 2017 Dec 1;27(23):5100-5108. (PMID: 29100802)
Langmuir. 2021 Mar 2;37(8):2693-2706. (PMID: 33595317)
J Med Chem. 2019 Oct 10;62(19):8665-8681. (PMID: 31063379)
Molecules. 2016 Jan 25;21(2):139. (PMID: 26821000)
Trends Pharmacol Sci. 2016 Aug;37(8):689-701. (PMID: 27267698)
Lancet Infect Dis. 2019 Jan;19(1):56-66. (PMID: 30409683)
Molecules. 2020 Oct 20;25(20):. (PMID: 33092246)
Int J Antimicrob Agents. 2003 Apr;21(4):364-91. (PMID: 12672587)
Int J Mol Sci. 2019 Feb 15;20(4):. (PMID: 30769917)
3 Biotech. 2017 Jul;7(3):172. (PMID: 28660459)
Antimicrob Agents Chemother. 1983 Jul;24(1):107-13. (PMID: 6414364)
Antimicrob Agents Chemother. 2000 Dec;44(12):3317-21. (PMID: 11083634)
Antibiotics (Basel). 2020 Jun 13;9(6):. (PMID: 32545761)
Nat Prod Rep. 2010 Feb;27(2):238-54. (PMID: 20111803)
J Mater Chem B. 2020 Jan 22;8(3):484-491. (PMID: 31834347)
J Asian Nat Prod Res. 2021 Feb;23(2):176-188. (PMID: 31888388)
Sci Rep. 2017 Mar 03;7:42717. (PMID: 28256516)
Bioinformatics. 2019 Mar 15;35(6):1067-1069. (PMID: 30165565)
Antimicrob Agents Chemother. 2000 Nov;44(11):2969-78. (PMID: 11036008)
Crit Rev Microbiol. 2019 May;45(3):301-314. (PMID: 30985240)
Soft Matter. 2014 Mar 21;10(11):1806-15. (PMID: 24652481)
EXCLI J. 2018 May 04;17:420-451. (PMID: 29805348)
Nucleic Acids Res. 2021 Jul 2;49(W1):W5-W14. (PMID: 33893803)
ChemMedChem. 2018 May 23;13(10):1018-1027. (PMID: 29465814)
Bioorg Khim. 2006 May-Jun;32(3):291-307. (PMID: 16808172)
Phytomedicine. 2020 Jul 15;73:152933. (PMID: 31103429)
Steroids. 2015 Aug;100:27-35. (PMID: 25963549)
Curr Drug Metab. 2004 Dec;5(6):483-505. (PMID: 15578943)
Curr Med Chem. 2021;28(17):3406-3448. (PMID: 33138746)
Drug Des Devel Ther. 2014 Oct 23;8:2075-88. (PMID: 25364233)
Steroids. 2020 Feb;154:108530. (PMID: 31678136)
J Antimicrob Chemother. 2010 Apr;65(4):799-801. (PMID: 20147322)
J Cheminform. 2018 Jun 26;10(1):29. (PMID: 29943074)
Nat Prod Res. 2021 Nov;35(21):3850-3858. (PMID: 32223360)
Phytomedicine. 2012 Apr 15;19(6):515-9. (PMID: 22341643)
فهرسة مساهمة: Keywords: antibiotic enhancers; antimicrobial activities; oleanolic acid; triterpenic polyamine conjugates
تواريخ الأحداث: Date Created: 20220121 Latest Revision: 20220128
رمز التحديث: 20231215
مُعرف محوري في PubMed: PMC8772916
DOI: 10.3390/antibiotics11010094
PMID: 35052971
قاعدة البيانات: MEDLINE
الوصف
تدمد:2079-6382
DOI:10.3390/antibiotics11010094