Item request has been placed! ×
Item request cannot be made. ×
loading  Processing Request

Synthesis, Bioactivity and Molecular Docking of Nereistoxin Derivatives Containing Phosphonate.

Item request has been placed! ×
Item request cannot be made. ×
loading   Processing Request
اقرأ على الانترنت اقرأ أكثر حفظ في قائمتي
  • معلومة اضافية
    • المصدر:
      Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE
    • بيانات النشر:
      Original Publication: Basel, Switzerland : MDPI, c1995-
    • الموضوع:
      Organophosphonates*/pharmacology ; Insecticides*/chemistry ; Aphids*/metabolism; Animals ; Humans ; Molecular Docking Simulation ; Molecular Structure ; Acetylcholinesterase/metabolism ; Structure-Activity Relationship
    • نبذة مختصرة :
      Novel nereistoxin derivatives containing phosphonate were synthesized and characterized via 31 P, 1 H and 13 C NMR and HRMS. The anticholinesterase activity of the synthesized compounds was evaluated on human acetylcholinesterase (AChE) using the in vitro Ellman method. Most of the compounds exhibited good inhibition of acetylcholinesterase. All of these compounds were selected to assess their insecticidal activity (in vivo) against Mythimna separata Walker, Myzus persicae Sulzer and Rhopalosiphum padi . Most of the tested compounds displayed potent insecticidal activity against these three species. Compound 7f displayed good activity against all three insect species, showing LC 50 values of 136.86 μg/mL for M. separata , 138.37 μg/mL for M. persicae and 131.64 μg/mL for R. padi . Compound 7b had the highest activity against M. persicae and R. padi , with LC 50 values of 42.93 μg/mL and 58.19 μg/mL, respectively. Docking studies were performed to speculate the possible binding sites of the compounds and explain the reasons for the activity of the compounds. The results showed that the compounds had lower binding energies with AChE than with the acetylcholine receptor (AchR), suggesting that compounds are more easily bound with AChE.
    • References:
      Toxicology. 2018 Dec 1;410:125-131. (PMID: 30266654)
      Biochem Pharmacol. 2004 Dec 1;68(11):2237-48. (PMID: 15498514)
      J Org Chem. 2011 May 20;76(10):4189-93. (PMID: 21466241)
      Pest Manag Sci. 2019 Sep;75(9):2301-2309. (PMID: 30672097)
      Org Process Res Dev. 2021 Nov 19;25(11):2453-2460. (PMID: 34840493)
      Bull Entomol Res. 2014 Feb;104(1):88-96. (PMID: 24229507)
      Annu Rev Pharmacol Toxicol. 1996;36:107-29. (PMID: 8725384)
      Pestic Biochem Physiol. 2019 Jun;157:122-137. (PMID: 31153459)
      Nanoscale. 2019 Oct 7;11(37):17230-17234. (PMID: 31531482)
      Expert Opin Ther Pat. 2017 Apr;27(4):455-476. (PMID: 27967267)
      Science. 2021 Sep 10;373(6560):1265-1270. (PMID: 34516793)
      J Agric Food Chem. 2021 Oct 6;69(39):11572-11581. (PMID: 34554742)
      Sci Rep. 2017 Jan 18;7:40634. (PMID: 28098188)
      Biochem Pharmacol. 1961 Jul;7:88-95. (PMID: 13726518)
      J Agric Food Chem. 2013 Aug 28;61(34):8148-55. (PMID: 23915199)
      Sci Total Environ. 2020 Aug 20;731:139071. (PMID: 32438088)
    • Contributed Indexing:
      Keywords: acetylcholinesterase inhibition; docking; insecticidal activity; nereistoxin; phosphonate
    • الرقم المعرف:
      EC 3.1.1.7 (Acetylcholinesterase)
      1631-58-9 (nereistoxin)
      0 (Organophosphonates)
      0 (Insecticides)
    • الموضوع:
      Date Created: 20230628 Date Completed: 20230629 Latest Revision: 20230701
    • الموضوع:
      20250114
    • الرقم المعرف:
      PMC10305189
    • الرقم المعرف:
      10.3390/molecules28124846
    • الرقم المعرف:
      37375402