Memantine derived compounds as potent in vitro inhibitors of urease: Repurposing of memantine, sonication assisted derivatization and in vitro enzyme inhibition, kinetics and molecular docking studies

Huang R, Southall N, Wang Y, Yasgar A, Shinn P, Jadhav A, et al. The NCGC pharmaceutical collection: A comprehensive resource of clinically approved drugs enabling repurposing and chemical genomics. Sci Transl Med. 2011;3:80ps16–80ps16.

Article  Google Scholar 

Sardana D, Zhu C, Zhang M, Gudivada RC, Yang L, Jegga AG. Drug repositioning for orphan diseases. Brief Bioinform. 2011;12:346–56.

Article  CAS  Google Scholar 

Ün İ, İbişoğlu H, Kılıç A, Ün ŞŞ, Yuksel F. Nucleophilic substitution reactions of adamantane derivatives with cyclophosphazenes. Inorg Chim Acta. 2012;387:226–33.

Article  Google Scholar 

Arshad N, Saeed A, Perveen F, Ujan R, Farooqi SI, Channar PA, et al. Synthesis, X-ray, Hirshfeld surface analysis, exploration of DNA binding, urease enzyme inhibition and anticancer activities of novel adamantane-naphthyl thiourea conjugate. Bioorg Chem. 2021;109:104707.

Article  CAS  Google Scholar 

Spilovska K, Zemek F, Korabecny J, Nepovimova E, Soukup O, Windisch M, et al. Adamantane–a lead structure for drugs in clinical practice. Curr Med Chem 2016;23:3245–66.

Article  CAS  Google Scholar 

de Roin S, Winters S. Amantadine hydrochloride: current and new uses. Can J Neurosci Nurs. 1990;22:322–5.

Article  Google Scholar 

Witt A, Macdonald N, Kirkpatrick P. Memantine hydrochloride. Nat Rev Drug Discov. 2004;3:109–10.

Article  CAS  Google Scholar 

Scholtissek C, Webster RG. Long-term stability of the anti-influenza A compounds—amantadine and rimantadine. Antivir Res. 1998;38:213–5.

Article  CAS  Google Scholar 

Stamataros G, Schneider SH. Vildagliptin in the treatment of type 2 diabetes mellitus. Expert Opin Pharmacother. 2011;12:1967–73.

Article  CAS  Google Scholar 

Shakeel A, Altaf AA, Qureshi AM, Badshah A. Thiourea derivatives in drug design and medicinal chemistry: A short review. J Drug Des Med Chem. 2016;2:10.

Google Scholar 

Sun YL, Wei Y, Shi M. Applications of chiral thiourea‐amine/phosphine organocatalysts in catalytic asymmetric reactions. ChemCatChem. 2017;9:718–27.

Article  CAS  Google Scholar 

Burmistrov V, Morisseau C, Pitushkin D, Karlov D, Fayzullin RR, Butov GM, et al. Adamantyl thioureas as soluble epoxide hydrolase inhibitors. Bioorg Med Chem Lett. 2018;28:2302–13.

Article  CAS  Google Scholar 

Al-Mutairi AA, Alagappan K, Blacque O, Al-Alshaikh MA, El-Emam AA, Percino MJ, et al. Crystallographic and theoretical exploration of weak hydrogen bonds in Arylmethyl N′-(adamantan-1-yl) piperidine-1-carbothioimidates and molecular docking analysis. ACS omega. 2021;6:27026–37.

Article  CAS  Google Scholar 

Liu J, Obando D, Liao V, Lifa T, Codd R. The many faces of the adamantyl group in drug design. Eur J Med Chem. 2011;46:1949–63.

Article  CAS  Google Scholar 

Mazzei L, Cianci M, Vara AG, Ciurli S. The structure of urease inactivated by Ag (I): A new paradigm for enzyme inhibition by heavy metals. Dalton Trans. 2018;47:8240–7.

Article  CAS  Google Scholar 

Vasiljev A, Simha P, Demisse N, Karlsson C, Randall DG, Vinnerås B. Drying fresh human urine in magnesium-doped alkaline substrates: Capture of free ammonia, inhibition of enzymatic urea hydrolysis & minimisation of chemical urea hydrolysis. J Chem Eng. 2022;428:131026.

Article  CAS  Google Scholar 

Hassan ST, Šudomová M. The development of urease inhibitors: What opportunities exist for better treatment of Helicobacter pylori infection in children? Children 2017;4:2.

Article  Google Scholar 

Rizvi F, Khan M, Jabeen A, Siddiqui H, Choudhary MI. Studies on isoniazid derivatives through a medicinal chemistry approach for the identification of new inhibitors of urease and inflammatory markers. Sci Rep. 2019;9:1–14.

Article  CAS  Google Scholar 

Bailie N, Osborne C, Leininger J, Fletcher T, Johnston S, Ogburn P, et al. Teratogenic effect of acetohydroxamic acid in clinically normal beagles. Am J Vet Res. 1986;47:2604–11.

CAS  Google Scholar 

Griffith DP, Gleeson MJ, Lee H, Longuet R, Deman E, Earle N. Randomized, double-blind trial of Lithostat™(Acetohydroxamic Acid) in the palliative treatment of infection-induced urinary calculi. Eur Urol. 1991;20:243–7.

Article  CAS  Google Scholar 

Milo S, Heylen RA, Glancy J, Williams GT, Patenall BL, Hathaway HJ, et al. A small-molecular inhibitor against Proteus mirabilis urease to treat catheter-associated urinary tract infections. Sci Rep. 2021;11:1–15.

Article  Google Scholar 

Raza M, Siddiqui H, Khan M, Ullah S, Rizvi F, Ahmad R, et al. Ultrasonic-assisted synthesis of amantadine derivatives-in vitro urease and α-glucosidase inhibitory activities, mechanistic, and computational studies. J Mol Struct. 2022;1266:133544.

Article  CAS  Google Scholar 

Liu Y, Myers EJ, Rydahl SA, Wang X. Ultrasonic-assisted synthesis, characterization, and application of a metal–organic framework: A green general chemistry laboratory project. J Chem Educ. 2019;96:2286–91.

Article  CAS  Google Scholar 

Anastas PT, Warner JC. Green Chemistry. Front. 1998;640:1998.

Google Scholar 

Naseem S, Ashraf M, Khan S, Rafiq M, Kashif M, Rahman J, et al. Exploring biologically active hybrid pharmacophore N-substituted hydrazine-carbothioamides for urease inhibition: In vitro and in silico approach. Int J Biol Macromol. 2021;182:534–44.

Article  CAS  Google Scholar 

Ahmed A, Saeed A, Ali OM, El-Bahy ZM, Channar PA, Khurshid A, et al. Exploring amantadine derivatives as urease inhibitors: Molecular docking and Structure–Activity Relationship (SAR) studies. Molecules 2021;26:7150.

Article  CAS  Google Scholar 

Rizvi F, Khan M, Jabeen A, Siddiqui H, Choudhary MI. Studies on isoniazid derivatives through a medicinal chemistry approach for the identification of new inhibitors of urease and inflammatory markers. Sci Rep. 2019;9:6738.

Article  Google Scholar 

Todd MJ, Hausinger RP. Fluoride inhibition of Klebsiella aerogenes urease: Mechanistic implications of a pseudo-uncompetitive, slow-binding inhibitor. Biochemistry 2000;39:5389–96.

Article  CAS  Google Scholar 

Siddiqui H, Bashir MA, Javaid K, Nizamani A, Bano H, Yousuf S, et al. Ultrasonic synthesis of tyramine derivatives as novel inhibitors of α-glucosidase in vitro. J Enzym Inhib Med Chem. 2016;31:1392–403.

Article  CAS  Google Scholar 

Pitushkin D, Burmistrov V, Butov G. Synthesis and Properties of N-(R-Adamantan-1-ylalkyl)-N′-[3 (4)-fluorophenyl] thioureas—Target-Oriented Human Soluble Epoxide Hydrolase (hsEH) Inhibitors. Russ J Org Chem. 2018;54:1469–74.

Article  CAS  Google Scholar 

Burmistrov V, Morisseau C, D’yachenko V, Rybakov VB, Butov GM, Hammock BD. Fluoroaromatic fragments on 1, 3-disubstituted ureas enhance soluble epoxide hydrolase inhibition. J Fluor Chem. 2019;220:48–53.

Article  CAS  Google Scholar 

Weatherburn M. Phenol-hypochlorite reaction for determination of ammonia. Anal Chem. 1967;39:971–4.

Article  CAS  Google Scholar 

Price P, McMillan TJ. Use of the tetrazolium assay in measuring the response of human tumor cells to ionizing radiation. Cancer Res. 1990;50:1392–6.

CAS  Google Scholar 

Mosmann T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J Immunol Methods. 1983;65:55–63.

Article  CAS  Google Scholar 

Leatherbarrow RJ. GraFit Version 7. Horley UK: Erithacus Software Ltd; 2009.

Google Scholar 

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