N-substituted aminomethanephosphonic and aminomethane-P-methylphosphinic acids
1945
Ashiralieva A, Kleiner
D
(2003) Polyhalogenated benzo- and
Kot M, Zaborska W, Juszkiewicz A (2000) Inhibition of jack bean
urease by thiols: Calorimetric studies. Thermochim Acta
354:63–69
naphthoquinones are potent inhibitors of plant and bacterial
urease. FEBS Lett 555:367–370
Benini S, Rypniewski WR, Wilson KS, Ciurli S, Mangani S (2001)
Structure-based rationalization of urease inhibition by phos-
phate: novel insights into the enzyme mechanism. J Biol Inorg
Chem 6:778–790
Benini S, Rypniewski WR, Wilson KS, Miletti S, Ciurli S, Mangani S
(2000) The complex of Bacillus pasteurii urease with acetohydr-
Krajewska B (2009) Ureases I functional catalytic and kinetic
properties: a review. J Mol Cat B 59:9–21
´
Kudzin ZH, Depczynski R, Andijewski G, Drabowicz J, Łuczak J
(2005) 1-(N-acylamino)alkanephosphonates Part IV. N-Acyla-
tion of 1-aminoalkanephosphonic Acids. Pol J Chem 79:499–513
Kuehler TC, Fryklund J, Bergman N, Weilitz J, Lee A, Larsson H
(1995) Structure-activity relationship of omeprazole and analogs
as Helicobacter pylori urease inhibitors. J Med Chem
38:4906–4916
Mobley HL, Hausinger RP (1989) Microbial ureases: significance
regulation and molecular characterization. Microbiol Rev
53:85–108
˚
oxamate anion from X-ray data at 1.55 A resolution. J Biol Inorg
Chem 5:110–118
Benini S, Rypniewski WR, Wilson KS, Miletti S, Ciurli S, Mangani S
(1999) A new proposal for urease mechanism based on the
crystal structures of the native and inhibited enzyme from
Bacillus pasteurii: why urea hydrolysis costs two nickels. Struct
Fold Des 7:205–216
Benini S, Gessa C, Ciurli S (1996) Bacillus pasteurii urease: a
heteropolymeric enzyme with a binuclear nickel active site. Soil
Biol Biochem 28:819–821
Burne RA, Chen YM (2000) Bacterial ureases in infectious diseases.
Microb Infect 2:533–542
Chaney AL, Marbach EP (1962) Modified reagents for determination
of urea and ammonia. Clin Chem 8:130–132
Chen XG, Correa P, Offerhaus J, Rodriguez E, Janney F, Hoffmann
E, Fox J, Hunter F, Diavolitsis S (1986) Ultrastructure of the
gastric mucosa harboring Campylobacter-like organisms. Am J
Clin Pathol 86:575–582
Dominguez MJ, Sanmartin C, Font M, Palop JA, San Francisco S,
Urrutia O, Houdusse F, Garcia-Mina JM (2008) Design synthesis
and biological evaluation of phosphoramide derivatives as urease
inhibitors. J Agric Food Chem 56:3721–3731
Mobley HLT, Island MD, Hausinger RP (1995) Molecular biology of
microbial ureases. Microbiol Rev 59:451–480
Nagata K, Satoh H, Iwahi T, Shimoyama T, Tamura T (1993) Potent
inhibitory action of the gastric proton pump inhibitor lansop-
razole against urease activity of Helicobacter pylori: unique
action selective for H. pylori cells. Antimicrob Agents Chemo-
ther 37:769–774
Odake S, Morikawa T, Tsuchiya M, Imamura L, Kobashi K (1994)
Inhibition of Heliocobacter pylori urease activity by hydroxamic
acid derivatives. Biol Pharm Bull 17:1329–1332
Odake S, Nakahashi K, Morikawa T, Takebe S, Kobashi K (1992)
Inhibition of Urease activity by dipeptidyl hydroxamic acids.
Chem Pharm Bull (Tokyo) 40:2764–2768
Pope AJ, Toseland CD, Rushant B, Richardson S, McVey M, Hills J
(1998) Effect of potent urease inhibitor, fluorofamide, on
Helicobacter sp. in vivo and in vitro. Dig Dis Sci 43:109–119
´
´
´
Faraci WS, Yang BV, O’Rourke D, Spencer RW (1995) Inhibition of
Helicobacter pylori urease by phenyl phosphorodiamidates:
mechanism of action. Bioorg Med Chem 3:605–610
Follmer C (2010) Ureases as a target for the treatment of gastric and
urinary infections. J Clin Pathol 63:424–430
Rohovec J, Luke I, Vojtıek P, Cısaova I, Hermann P (1996)
Complexing properties of phosphinic analogs of glycine.
J Chem Soc Dalton Trans 1996:2685–2691
Sahrawat KL (1980) Control of urea hydrolysis and nitrification in
soil by chemicals. Prospects and problems. Plant Soil 57:335–
352
Sivapriya K, Suguna P, Banerjee A, Saravanan V, Rao DN,
Chandrasekaran S (2007) Facile one-pot synthesis of thio and
selenourea derivatives: a new class of potent urease inhibitors.
Bioorg Med Chem Lett 17:6387–6391
Soriano F, Tauch A (2008) Microbiology and Clinical Features of
Corynebacterium urealyticum: urinary tract stones and genomics
as the rosetta stone. Clin Microbiol Infect 14:632–643
Todd MJ, Hausinger RP (1989) Competitive inhibitors of Klebsiella
aerogenes urease. Mechanisms of interaction with the nickel
active site. J Biol Chem 264:15835–15842
Gioacchini P, Nastri A, Marzadori C, Giovannini C, Vittori AL,
Gessa C (2002) Influence of urease and nitrification inhibitors on
N losses from soils fertilized with urea. Biol Fert Soil
36:129–135
Goodwin CS, Armstrong JA, Marshall BJ (1986) Campylobacter
pyloridis gastritis and peptic ulceration. J Clin Pathol 39:353–
365
Griffith DP (1979) Urease stones. Urol Res 7:215–221
Ham NC, Oh ST, Sung JY, Cha KA, Lee MH, Oh BH (2001)
Supramolecular assembly and acid resistance of Helicobacter
pylori urease. Nat Struct Biol 8:505–509
Hulme AN, Rosser EM (2002) An aldol-based approach to the
synthesis of the antibiotic anisomycin. Org Lett 4:265–267
Karp GM (1999) An expeditious route to novel 142-benzodiazapho-
sphepin-5-one 2-oxide analogues. J Org Chem 64:8156–8160
Karplus PA, Pearson MA, Hausinger RP (1997) 70 years of
crystalline urease: what have we learned? Acc Chem Res
30:330–337
Tyka R, Hagele GA (1984) convenient synthesis of N-alkylamino-
methanephosphonic and N-alkylaminomethanephosphinic acids.
Synthesis 1984:218–219
Vassiliou S, Grabowiecka A, Kosikowska P, Yiotakis A, Kafarski P,
Berlicki Ł (2008) Design synthesis and evaluation of novel
organophosphorus inhibitors of bacterial urease. J Med Chem
51:5736–5744
Kobashi K, Hase J, Uehare K (1962) Specific inhibition of urease by
hydroxamic acids. Biochim Biophys Acta 65:380–383
Kobashi K, Kumaki K, Hase J (1971) Effect of acyl residues of
hydroxamic acids on urease inhibition. Biochim Biophys Acta
227:429–441
Kobashi K, Takebe S, Terashima N, Hase J (1975) Inhibition of
urease activity by hydroxamic acid derivatives of amino acids.
J Biochem (Tokyo) 77:837–843
Vassiliou S, Grabowiecka A, Kosikowska P, Yiotakis A, Kafarski P,
Berlicki Ł (2010) Computer-aided optimization of phosphinic
inhibitors of bacterial ureases. J Med Chem 53:5597–5606
Vuye A, Pijck J (1973) Urease activity of Enterobacteriaceae: which
medium to choose. Appl Environ Microbiol 26:850–854
Worcester EM, Coe FL (2008) Nephrolithiasis. Prim Care
35:369–391
Zaborska W, Kot M, Superata K (2002) Inhibition of Jack Bean
Urease by 14-benzoquinone and 25-dimethyl-14-benzoquinone.
Evaluation of the inhibition mechanism. J Enzyme Inhib Med
Chem 17:247–253
Kosikowska P, Berlicki Ł (2011) Urease inhibitors as potential drugs
for gastric and urinary tract infections: a patent review. Expert
123