Academic Journal
Exploring Substituted Dihydroxybenzenes as Urease Inhibitors through Structure-Activity Relationship Studies in Soil Incubations.
| Τίτλος: | Exploring Substituted Dihydroxybenzenes as Urease Inhibitors through Structure-Activity Relationship Studies in Soil Incubations. |
|---|---|
| Συγγραφείς: | Nathanael JG; School of Chemistry, ARC Research Hub for Smart Fertilisers, The University of Melbourne, Parkville, Victoria, 3010, Australia., Kang H; School of Chemistry, ARC Research Hub for Smart Fertilisers, The University of Melbourne, Parkville, Victoria, 3010, Australia., Wille U; School of Chemistry, ARC Research Hub for Smart Fertilisers, The University of Melbourne, Parkville, Victoria, 3010, Australia. |
| Πηγή: | ChemPlusChem [Chempluschem] 2025 Aug; Vol. 90 (8), pp. e202500068. Date of Electronic Publication: 2025 Jun 20. |
| Τύπος έκδοσης: | Journal Article |
| Γλώσσα: | English |
| Στοιχεία περιοδικού: | Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 101580948 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 2192-6506 (Electronic) Linking ISSN: 21926506 NLM ISO Abbreviation: Chempluschem Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: Weinheim, Germany : Wiley-VCH, [c2012]- |
| Ιατρικοί όροι (MeSH): | Urease*/antagonists & inhibitors , Urease*/metabolism , Soil*/chemistry , Enzyme Inhibitors*/chemistry , Enzyme Inhibitors*/pharmacology , Enzyme Inhibitors*/metabolism , Enzyme Inhibitors*/chemical synthesis, Urea/metabolism ; Urea/chemistry ; Structure-Activity Relationship ; Kinetics ; Density Functional Theory ; Molecular Structure ; Organophosphorus Compounds |
| Περίληψη: | Urea fertilization as nitrogen (N) source is essential for increasing crop productivity. However, it results in significant N loss through ammonia volatilization, nitrate leaching, and nitrous oxide emissions, causing environmental harm and economic loss. Urease, an enzyme in soil, rapidly catalyzes urea hydrolysis to ammonia/ammonium. To reduce ammonia volatilization, urease inhibitors delay hydrolysis until urea is dissolved in the soil body. The commercial product N-(n-butyl)thiophosphoric triamide (NBPT) is effective only in certain soils, yet it dominates the current global urease inhibitor market. This study examines the performance of un- and substituted dihydroxybenzenes (DHBs) as alternatives to NBPT in two Australian soils. Among them, 4-fluorocatechol (DHB 6) and 4-bromocatechol (DHB 8) are more effective in delaying urea hydrolysis than NBPT in acidic sandy loam soil. Michaelis-Menten kinetics reveals that NBPT acts as a competitive inhibitor, while DHB 8 acts as a noncompetitive inhibitor. Density functional theory calculations suggest that DHB 8 binds to the cysteine residue in the urease mobile flap, reducing its flexibility and preventing it from assisting urea hydrolysis. This study demonstrates the potential of DHBs as efficient urease inhibitors in certain soils, offering an environmentally viable alternative to NBPT. (© 2025 The Author(s). ChemPlusChem published by Wiley‐VCH GmbH.) |
| References: | Microbiol Rev. 1989 Mar;53(1):85-108. (PMID: 2651866) Angew Chem Int Ed Engl. 2021 Mar 8;60(11):6029-6035. (PMID: 33245574) J Org Chem. 2022 Apr 1;87(7):4580-4589. (PMID: 35266705) J Chem Phys. 2010 Apr 21;132(15):154104. (PMID: 20423165) Annu Rev Phytopathol. 1974;12:139-65. (PMID: 23249125) Sci Total Environ. 2019 May 1;663:889-900. (PMID: 30738268) Nature. 2015 Dec 3;528(7580):51-9. (PMID: 26595273) J Agric Food Chem. 2008 May 28;56(10):3721-31. (PMID: 18452297) J Agric Food Chem. 2019 Feb 27;67(8):2127-2138. (PMID: 30735374) Environ Res. 2023 Apr 15;223:115311. (PMID: 36731597) Science. 2021 Nov 05;374(6568):758-762. (PMID: 34735244) J Inorg Biochem. 2017 Jan;166:182-189. (PMID: 27888701) Physiol Plant. 2018 Feb;162(2):251-260. (PMID: 29095491) J Adv Res. 2018 May 24;13:19-27. (PMID: 30094079) IUBMB Life. 2002 Feb;53(2):85-98. (PMID: 12049200) Chemistry. 2004 Feb 20;10(4):933-9. (PMID: 14978819) Sci Total Environ. 2018 Dec 10;644:1531-1535. (PMID: 30743866) J Sci Food Agric. 2011 Jul;91(9):1569-75. (PMID: 21656770) Sci Rep. 2015 Oct 30;5:15842. (PMID: 26514559) J Chem Theory Comput. 2005 Jan;1(1):70-7. (PMID: 26641117) J Med Chem. 2019 May 9;62(9):4350-4369. (PMID: 30951312) J Hazard Mater. 2006 Jun 30;134(1-3):161-8. (PMID: 16343761) Philos Trans R Soc Lond B Biol Sci. 2013 May 27;368(1621):20130116. (PMID: 23713116) Eur J Biochem. 1967 Oct;2(3):327-31. (PMID: 4865316) Sci Total Environ. 2020 Mar 1;706:135124. (PMID: 31855649) |
| Grant Information: | IH200100023 the Australian Research Council through the ARC Research Hub for Smart Fertilizers; DP200101162 the Australian Research Council through the ARC Research Hub for Smart Fertilizers; LP160101417 the Australian Research Council through the ARC Research Hub for Smart Fertilizers |
| Contributed Indexing: | Keywords: N‐(n‐butyl)thiophosphoric triamide; density functional calculations; inhibition mechanism; inhibitors; soil incubation; urease |
| Substance Nomenclature: | EC 3.5.1.5 (Urease) 0 (Soil) 0 (Enzyme Inhibitors) 8W8T17847W (Urea) 0 (N-(n-butyl) thiophosphoric triamide) 0 (Organophosphorus Compounds) |
| Entry Date(s): | Date Created: 20250531 Date Completed: 20250826 Latest Revision: 20260127 |
| Update Code: | 20260130 |
| PubMed Central ID: | PMC12352726 |
| DOI: | 10.1002/cplu.202500068 |
| PMID: | 40448662 |
| Βάση Δεδομένων: | MEDLINE |
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