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Research Article

Design, synthesis and anticholinesterase activity of some new α-aminobisphosphonates

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Pages 827-835 | Received 06 Sep 2009, Accepted 10 Feb 2010, Published online: 30 Mar 2010

References

  • Rodan GA, Martin TJ. Therapeutic approaches to bone diseases. Science 2000; 289:1508–1514.
  • Hirabayashi H, Sawamoto T, Fujisaki J, Tokunaga Y, Kimura S, Hata T. Dose-dependent pharmacokinetics and disposition of bisphosphonic prodrug of diclofenac based on osteotropic drug delivery system (ODDS). Biopharm Drug Dispos 2002; 23:307–315.
  • Vieillard MH, Maes JM, Penel G, Facon T, Magro L, Bonneterre J, Cortet B. Thirteen cases of jaw osteonecrosis in patients on bisphosphonate therapy. Joint Bone Spine 2008; 75:34–40.
  • Dannemann C, Grätz KW, Riener MO, Zwahlen RA. Jaw osteonecrosis related to bisphosphonate therapy: A severe secondary disorder. Bone 2007; 40:828–834.
  • Widler L, Jaeggi KA, Glatt M, Muller K, Bachmann R, Bisping M, Born A-R Cortesi, R, Guiglia G, Jeker H, Klein R, Ramseier U, Schmid J, Schreiber G, Seltenmeyer Y, Green JR.Highly Potent Geminal Bisphosphonates. From Pamidronate Disodium (Aredia) to Zoledronic Acid (Zometa). J Med Chem 2002; 45:3721–3738.
  • Houghton TJ, Tanaka KSE, Kang T, Dietrich E, Lafontaine Y, Delorme D, Ferreira SS, Viens F, Arhin FF, Sarmiento I, Lehoux D, Fadhil I, Laquerre K, Liu J, Ostiguy V, Poirier H, Moeck G, Parr Jr TR, Far AR. Linking bisphosphonates to the free amino groups in fluoroquinolones: preparation of osteotropic prodrugs for the prevention of osteomyelitis. J Med Chem 2008; 51:6955–6969.
  • Coleman RE. Optimising treatment of bone metastases by aredia and zometa. Breast Cancer 2000; 7:361–369.
  • Simoni D, Gebbia N, Invidiata FP, Eleopra M, Marchetti P, Rondanin R, Baruchello R, Provera S, Marchioro C, Tolomeo M, Marinelli L, Limongelli V, Novellino E, Kwaasi A, Dunford J, Buccheri S, Caccamo N, Dieli F. Design, synthesis, and biological evaluation of novel aminobisphosphonates possessing an in vivo antitumor activity through a γδ-T lymphocytes-mediated activation mechanism. J Med Chem 2008; 51:6800–6807.
  • Das H, Wang L, Kamath A, Bukowski JF. V{gamma}2V{delta}2 T-cell receptor-mediated recognition of aminobisphosphonates. Blood 2001; 98:1616–1618.
  • Kiran YB, Reddy CD, Gunasekar D, Reddy CS, Leon A, Barbosa LCA. Synthesis and anticancer activity of new class of bisphosphonates/phosphanamidates. European J Med Chem 2008; 43:885–892.
  • Makhaeva GF, Aksinenko AY, Sokolov VB, Serebryakova OG, Richardson RJ. Synthesis of organophosphates with fluorine-containing leaving groups as serine esterase inhibitors with potential for Alzheimer disease therapeutics. Bioorganic & Medicinal Chemistry Letters 2009; 19:5528–5530.
  • Grutzendler J, Morris JC. Cholinesterase Inhibitors for Alzheimer’s Disease. Drugs 2001; 61:41–52.
  • McKenna CE, Kashemirov BA, Rozé CN. Carbonylbisphosphonate and (diazomethylene)bisphosphonate analogues of AZT 5′-diphosphate. Bioorg Chem 2002; 30:383–395.
  • Kafarski P, Lejczak B, Forlani G, Gancarz R, Torreilles C, Grembecka J, Ryczek A, Wieczorek PJ.Herbicidal derivatives of sminomethylenebisphosphonic acid. Part III. Structure-Activity Relationship. Plant Growth Regul 1997; 16:153–158.
  • Martin MB, Sanders JM, Kendrick H, de Luca-Fradley K, Lewis JC, Grimley JS, Van Brussel EM, Olsen JR, Meints GA, Burzynska A, Kafarski P, Croft SL, Oldfield E.Activity of bisphosphonates against Trypanosoma brucei rhodesiense. J Med Chem 2002; 45:2904–2914.
  • Obojska A, Berlicki L, Kafarski P, Lejczak B, Chicca M, Forlani G.Herbicidal pyridyl derivatives of aminomethylene-bisphosphonic acid inhibit plant glutamine synthetase. J Agric Food Chem 2004; 52:3337–3344.
  • Kishore GM, Shah DM. Amino acid biosynthesis inhibitors as herbicides. Annu Rev Biochem 1988; 57:627–663.
  • Mori I, Iwasaki G, Hayakawa KJ. Rational design of a new herbicide by inhibition of histidine biosynthesis Design and synthesis of inhibitors of imidazole glycerol phosphate dehydratase (IGPD). Yuki Gosei Kagaku Kyokaishi/ J Synth Org Chem Jpn 1996; 54:62–72.
  • Kafarski PLB, Forlani G. Biodegradation of pesticides containing carbon-to-phosphorus bond. In: Hall JC, Hoagland RE, Zablotowicz RM., Eds. Pesticide Biotransformation in Plants and Microorganisms, American Chemical Society: ACS Symposium Series 777; Washington DC, 2001: 145–163.
  • Chen M-H, Chen Z, Song B-A, Bhadury PS, Yang S, Cai X-J, Hu D-Y, Xue W, Zeng S. Synthesis and Antiviral Activities of Chiral Thiourea Derivatives Containing an α-Aminophosphonate Moiety. J Agric Food Chem 2009; 57: 1383–1388.
  • Cibičková L, Palička V, Cibiček N, Čermáková E, Mičuda S, Bartošová L, Jun D. Differential effects of statins and alendronate on cholinesterases in serum and brain of rats. Physiol Res 2007; 56:765–770.
  • Cibičková Ľ, Hyšpler R, Cibiček N, Čermáková E, Palička V. Alendronate lowers cholesterol synthesis in the central nervous system of rats–a preliminary study. Physiol Res 2009; 58:455–458.
  • Golivand K, Abdollahi M, Mojahed F, Madani Alizadegan A, Dehghan G. Acetylcholinesterase/butyrylcholinesterase inhibition activity of some new carbacylamidophosphate deriviatives. J Enzyme Inhib Med Chem 2009; 24:566–576.
  • Golivand K, Mojahed F, Salehi M, Naderimanesh H, Khajeh K. Synthesis, characterization and inhibitory potency of two oxono and thiono analogues of phosphoramidate compounds on acetylcholinesterase. J Enzyme Inhib Med Chem 2006; 21:521–525.
  • Golivand K, Madani Alizadegan A, Anraki F, Khajeh K, Naderimanesh H, Bijanzadeh H. Anticholinesterase activity of some major intermediates in carbacylamidophosphate synthesis: Preparation, spectral characterization and inhibitory potency determination. J Enzyme Inhib Med Chem 2006; 21:105–111.
  • Golivand K, Shariatinia Z, Khajeh K, Naderimanesh H. Syntheses and spectroscopic characterization of some phosphoramidates as reversible inhibitors of human acetylcholinesterase and determination of their potency. J Enzyme Inhib Med Chem 2006; 21:31–35.
  • Moedritzer K, Irani RR. The Direct synthesis of α-aminomethylphosphonic acids. Mannich-type reactions with orthophosphorous acid. J Org Chem 1966; 31:1603–1607.
  • Ellman GL, Courtney KD, Andres V, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961; 7:88–90.
  • Kitz R, Wilson IB. Esters of methanesulfuric acid as irreversible inhibitors of acetylcholinesterase. J Biol Chem 1962; 237:3245–3249.
  • Copeland RA. Enzymes, a Practical Introduction to Structure, Mechanism, and Data Analysis. 2nd ed. New York: John Wiley & Sons, 2000 ; p109–145.
  • Ariёns EJ. Drug Design. New York: Academic press, 1971: Vol II, p 129–149.
  • Thompson CM, Suarez AI, Rodriguez OP. Synthesis and 31P chemical shift identification of tripeptide active side models that represent human serum acetylcholinesterase covalently modified at serine by certain organophosphates. Chem Res Toxicol 1996; 9:1325–1332.
  • Waterhouse RN. Determination of lipophilicity and its use as a predictor of blood–brain barrier penetration of molecular imaging agents. Mol Imaging and Biol 2003; 5:376–389.
  • Ghadimi S, Ebrahimi ASV, Pourayoubi M, Samani KA. Structure-activity study of phosphoramido acid esters as acetylcholinesterase inhibitors. J Enzyme Inhib Med Chem 2008; 23:556–561.
  • Ashani Y, Segev O, Balan A. The effect of fluoride on the scavenging of organophosphates by human butyrylcholinesterase in buffer solutions and human plasma. Toxicol Appl Pharmacol 2004; 194:90–99.
  • Fukuto TR. Mechanism of action of organophosphorus and carbamate insecticides. Environ health persp 1990; 87:245–254.
  • Bożena Bukowska Katarzyna, Hutnik. 2,4-D and MCPA and their derivatives: Effect on the activity of membrane erythrocytes acetylcholinesterase (in vitro). Pestic Biochem Phys 2006; 5:174–180.

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