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The influence of N-alkyl chains in benzoyl-thiourea derivatives on urease inhibition: Soil studies and biophysical and theoretical investigations on the mechanism of interaction.

التفاصيل البيبلوغرافية
العنوان: The influence of N-alkyl chains in benzoyl-thiourea derivatives on urease inhibition: Soil studies and biophysical and theoretical investigations on the mechanism of interaction.
المؤلفون: Tavares MC; Instituto de Química e Biotecnologia, Universidade Federal de Alagoas, Maceió, AL, Brazil; Instituto Federal de Educação, Ciência e Tecnologia de Alagoas, Campus Batalha, AL, Brazil., Dos Santos Nascimento IJ; Instituto de Química e Biotecnologia, Universidade Federal de Alagoas, Maceió, AL, Brazil., de Aquino TM; Instituto de Química e Biotecnologia, Universidade Federal de Alagoas, Maceió, AL, Brazil., de Oliveira Brito T; Departamento de Química, Centro de Ciências Exatas, Universidade Estadual de Londrina, Londrina, PR, Brazil., Macedo F Jr; Departamento de Química, Centro de Ciências Exatas, Universidade Estadual de Londrina, Londrina, PR, Brazil., Modolo LV; Departamento de Botânica, Instituto de Ciências Biológicas, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil., de Fátima Â; Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil. Electronic address: adefatima@qui.ufmg.br., Santos JCC; Instituto de Química e Biotecnologia, Universidade Federal de Alagoas, Maceió, AL, Brazil. Electronic address: josue@iqb.ufal.br.
المصدر: Biophysical chemistry [Biophys Chem] 2023 Aug; Vol. 299, pp. 107042. Date of Electronic Publication: 2023 May 24.
نوع المنشور: Journal Article; Research Support, Non-U.S. Gov't
اللغة: English
بيانات الدورية: Publisher: Elsevier Science B.V Country of Publication: Netherlands NLM ID: 0403171 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1873-4200 (Electronic) Linking ISSN: 03014622 NLM ISO Abbreviation: Biophys Chem Subsets: MEDLINE
أسماء مطبوعة: Publication: Amsterdam : Elsevier Science B.V
Original Publication: Amsterdam, North-Holland Pub. Co.
مواضيع طبية MeSH: Soil* , Helicobacter pylori*/metabolism, Humans ; Urease/chemistry ; Urease/metabolism ; Fertilizers/analysis ; Urea/chemistry ; Enzyme Inhibitors/pharmacology ; Thiourea ; Biophysics
مستخلص: Ureases are enzymes produced by fungi, plants, and bacteria associated with agricultural and clinical problems. The urea hydrolysis in NH 3 and CO 2 leads to the loss of N-urea fertilizers in soils and changes the human stomach microenvironment, favoring the colonization of H. pylori. In this sense, it is necessary to evaluate potential enzyme inhibitors to mitigate the effects of their activities and respond to scientific and market demands to produce fertilizers with enhanced efficiency. Thus, biophysical and theoretical studies were carried out to evaluate the influence of the N-alkyl chain in benzoyl-thiourea derivatives on urease enzyme inhibition. A screening based on IC 50 , binding constants, and theoretical studies demonstrated that BTU1 without the N-alkyl chain (R = H) was more active than other compounds, so the magnitude of the interaction was determined as BTU1 > BTU2 > BTU3 > BTU4 > BTU5, corresponding to progressively increased chain length. Thus, BTU1 was selected for interaction and soil application essays. The binding constants (K b ) for the supramolecular urease-BTU1 complex ranged from 7.95 to 5.71 × 10 3  M -1 at different temperatures (22, 30, and 38 °C), indicating that the preferential forces responsible for the stabilization of the complex are hydrogen bonds and van der Waals forces (ΔH = -15.84 kJ mol -1 and ΔS = -36.61 J mol -1  K -1 ). Theoretical and experimental results (thermodynamics, synchronous fluorescence, and competition assay) agree and indicate that BTU1 is a mixed inhibitor. Finally, urease inhibition was evaluated in the four soil samples, where BTU1 was as efficient as NBPT (based on ANOVA two-way and Tukey test with 95% confidence), with an average inhibition of 20% of urease activity. Thus, the biophysics and theoretical studies are strategies for evaluating potential inhibitors and showed that increasing the N-alkyl chain in benzoyl-thiourea derivatives did not favor urease inhibition.
Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have influenced the work reported in this paper.
(Copyright © 2023. Published by Elsevier B.V.)
فهرسة مساهمة: Keywords: Enzymatic inhibition; Soil; Spectroscopic studies; Thioureas derivatives
المشرفين على المادة: 0 (Soil)
EC 3.5.1.5 (Urease)
0 (Fertilizers)
8W8T17847W (Urea)
0 (Enzyme Inhibitors)
GYV9AM2QAG (Thiourea)
تواريخ الأحداث: Date Created: 20230601 Date Completed: 20230614 Latest Revision: 20230614
رمز التحديث: 20240628
DOI: 10.1016/j.bpc.2023.107042
PMID: 37263179
قاعدة البيانات: MEDLINE
الوصف
تدمد:1873-4200
DOI:10.1016/j.bpc.2023.107042