메뉴 건너뛰기




Volumn 56, Issue 8, 2012, Pages 4483-4486

2-alkylaminoethyl-1,1-bisphosphonic acids are potent inhibitors of the enzymatic activity of Trypanosoma cruzi squalene synthase

Author keywords

[No Author keywords available]

Indexed keywords

1,1 BISPHOSPHONIC ACID DERIVATIVE; BISPHOSPHONIC ACID DERIVATIVE; GERANYLTRANSFERASE; SQUALENE SYNTHASE; SQUALENE SYNTHASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 84864386774     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.00796-12     Document Type: Article
Times cited : (17)

References (41)
  • 1
    • 0015869325 scopus 로고
    • Biology of Trypanosoma cruzi
    • Brener Z. 1973. Biology of Trypanosoma cruzi. Annu. Rev. Microbiol. 27:347-382.
    • (1973) Annu. Rev. Microbiol. , vol.27 , pp. 347-382
    • Brener, Z.1
  • 2
    • 4744357516 scopus 로고    scopus 로고
    • Inhibition of isoprene biosynthesis pathway enzymes by phosphonates, bisphosphonates, and diphosphates
    • Cheng F, Oldfield E. 2004. Inhibition of isoprene biosynthesis pathway enzymes by phosphonates, bisphosphonates, and diphosphates. J. Med. Chem. 47:5149 -5158.
    • (2004) J. Med. Chem. , vol.47 , pp. 5149-5158
    • Cheng, F.1    Oldfield, E.2
  • 3
    • 0027436434 scopus 로고
    • Lipophilic 1,1-bisphosphonates are potent squalene synthase inhibitors and orally active cholesterol lowering agents in vivo
    • Ciosek CP, Jr, et al. 1993. Lipophilic 1,1-bisphosphonates are potent squalene synthase inhibitors and orally active cholesterol lowering agents in vivo. J. Biol. Chem. 268:24832-24837.
    • (1993) J. Biol. Chem. , vol.268 , pp. 24832-24837
    • Ciosek Jr., C.P.1
  • 4
    • 33646383590 scopus 로고    scopus 로고
    • Recent advances in understanding the mechanism of action of bisphosphonates
    • DOI 10.1016/j.coph.2006.03.005, PII S1471489206000610, Respiratory/Musculoskeletal
    • Coxon FP, Thompson K, Rogers MJ. 2006. Recent advances in understanding the mechanism of action of bisphosphonates. Curr. Opin. Pharmacol. 6:307-312. (Pubitemid 43670914)
    • (2006) Current Opinion in Pharmacology , vol.6 , Issue.3 , pp. 307-312
    • Coxon, F.P.1    Thompson, K.2    Rogers, M.J.3
  • 5
    • 44349178631 scopus 로고    scopus 로고
    • The acidocalcisome as a target for chemotherapeutic agents in protozoan parasites
    • DOI 10.2174/138161208784041079
    • Docampo R, Moreno SNJ. 2008. The acidocalcisome as a target for chemotherapeutic agents in protozoan parasites. Curr. Pharm. Des. 14:882-888. (Pubitemid 351736420)
    • (2008) Current Pharmaceutical Design , vol.14 , Issue.9 , pp. 882-888
    • Docampo, R.1    Moreno, S.N.J.2
  • 7
    • 33846026392 scopus 로고    scopus 로고
    • A solanesyl-diphosphate synthase localizes in glycosomes of Trypanosoma cruzi
    • Ferella M, et al. 2006. A solanesyl-diphosphate synthase localizes in glycosomes of Trypanosoma cruzi. J. Biol. Chem. 281:39339 -39348.
    • (2006) J. Biol. Chem. , vol.281 , pp. 39339-39348
    • Ferella, M.1
  • 8
    • 0014029045 scopus 로고
    • Effect of pyrophosphate on hydroxyapatite and its implications in calcium homeostasis
    • Fleisch H, Russell RGG, Straumann F. 1966. Effect of pyrophosphate on hydroxyapatite and its implications in calcium homeostasis. Nature 212: 901-903.
    • (1966) Nature , vol.212 , pp. 901-903
    • Fleisch, H.1    Russell, R.G.G.2    Straumann, F.3
  • 9
    • 0014684354 scopus 로고
    • Diphosphonates inhibit hydroxyapatite dissolution in vitro and bone resorption in tissue culture and in vivo
    • Fleisch H, Russell RGG, Francis MD. 1969. Diphosphonates inhibit hydroxyapatite dissolution in vitro and bone resorption in tissue culture and in vivo. Science 165:1262-1264.
    • (1969) Science , vol.165 , pp. 1262-1264
    • Fleisch, H.1    Russell, R.G.G.2    Francis, M.D.3
  • 10
    • 0014684364 scopus 로고
    • Diphosphonates inhibit formation of calcium phosphate crystals in vitro and pathological calcification in vivo
    • Francis MD, Russell RGG, Fleisch H. 1969. Diphosphonates inhibit formation of calcium phosphate crystals in vitro and pathological calcification in vivo. Science 165:1264 -1266.
    • (1969) Science , vol.165 , pp. 1264-1266
    • Francis, M.D.1    Russell, R.G.G.2    Fleisch, H.3
  • 11
    • 0029917241 scopus 로고    scopus 로고
    • Risk factors for Trypanosoma cruzi infection in California blood donors
    • Galel SA, Kirchhoff LV. 1996. Risk factors for Trypanosoma cruzi infection in California blood donors. Transfusion 36:227-231. (Pubitemid 26114464)
    • (1996) Transfusion , vol.36 , Issue.3 , pp. 227-231
    • Galel, S.A.1    Kirchhoff, L.V.2
  • 13
    • 33646725498 scopus 로고    scopus 로고
    • The molecular mechanism of nitrogencontaining bisphosphonates as antiosteoporosis drugs
    • Kavanagh KL, et al. 2006. The molecular mechanism of nitrogencontaining bisphosphonates as antiosteoporosis drugs. Proc. Natl. Acad. Sci. U. S. A. 103:7829 -7834.
    • (2006) Proc. Natl. Acad. Sci. U. S. A. , vol.103 , pp. 7829-7834
    • Kavanagh, K.L.1
  • 14
    • 0027924584 scopus 로고
    • Current concepts: American trypanosomiasis (Chagas' disease) - A tropical disease now in the United States
    • DOI 10.1056/NEJM199308263290909
    • Kirchhoff LV. 1993. American trypanosomiasis (Chagas' disease) - a tropical disease now in the United States. N. Engl. J. Med. 329:639-644. (Pubitemid 23244817)
    • (1993) New England Journal of Medicine , vol.329 , Issue.9 , pp. 639-644
    • Kirchhoff, L.V.1
  • 15
    • 10544241192 scopus 로고    scopus 로고
    • Enantioselective synthesis of α-phosphono sulfonate squalene synthase inhibitors: Chiral recognition in the interactions of an α-phosphono sulfonate inhibitor with squalene synthase
    • Lawrence RM, et al. 1996. Enantioselective synthesis of α-phosphono sulfonate squalene synthase inhibitors: chiral recognition in the interactions of an α-phosphono sulfonate inhibitor with squalene synthase. J. Am. Chem. Soc. 118:11668 -11669.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11668-11669
    • Lawrence, R.M.1
  • 16
    • 33645883558 scopus 로고    scopus 로고
    • Progresses in the field of drug design to combat tropical protozoan parasitic diseases
    • Liñares GE, Ravaschino EL, Rodriguez JB. 2006. Progresses in the field of drug design to combat tropical protozoan parasitic diseases. Curr. Med. Chem. 13:335-360.
    • (2006) Curr. Med. Chem. , vol.13 , pp. 335-360
    • Liñares, G.E.1    Ravaschino, E.L.2    Rodriguez, J.B.3
  • 18
    • 0029011739 scopus 로고
    • 1,1-Bisphosphonate squalene synthase inhibitors: Interplay between the isoprenoid subunit and the diphosphate surrogate
    • Magnin DR, et al. 1995. 1,1-Bisphosphonate squalene synthase inhibitors: interplay between the isoprenoid subunit and the diphosphate surrogate. J. Med. Chem. 38:2596 -2605.
    • (1995) J. Med. Chem. , vol.38 , pp. 2596-2605
    • Magnin, D.R.1
  • 19
    • 19244368781 scopus 로고    scopus 로고
    • α-Phosphonosulfonic acids: Potent and selective inhibitors of squalene synthase
    • Magnin DR, et al. 1996. α-Phosphonosulfonic acids: potent and selective inhibitors of squalene synthase. J. Med. Chem. 39:657- 660.
    • (1996) J. Med. Chem. , vol.39 , pp. 657-660
    • Magnin, D.R.1
  • 20
    • 0035866666 scopus 로고    scopus 로고
    • Bisphosphonates inhibit the growth of Trypanosoma brucei, Trypanosoma cruzi, Leishmania donovani, Toxoplasma gondii, and Plasmodium falciparum: A potential route to chemotherapy
    • Martin MB, et al. 2001. Bisphosphonates inhibit the growth of Trypanosoma brucei, Trypanosoma cruzi, Leishmania donovani, Toxoplasma gondii, and Plasmodium falciparum: a potential route to chemotherapy. J. Med. Chem. 44:909 -916.
    • (2001) J. Med. Chem. , vol.44 , pp. 909-916
    • Martin, M.B.1
  • 21
    • 0030047147 scopus 로고    scopus 로고
    • Inhibition of squalene synthase of rat liver by novel 3= substituted quimuclidines
    • McTaggart F, et al. 1996. Inhibition of squalene synthase of rat liver by novel 3= substituted quimuclidines. Biochem. Pharmacol. 51:1477-1487.
    • (1996) Biochem. Pharmacol. , vol.51 , pp. 1477-1487
    • McTaggart, F.1
  • 22
    • 77956975241 scopus 로고    scopus 로고
    • Targeting isoprenoid biosynthesis for drug discovery: Bench to bedside
    • Oldfield E. 2010. Targeting isoprenoid biosynthesis for drug discovery: bench to bedside. Acc. Chem. Res. 43:1216 -1226.
    • (2010) Acc. Chem. Res. , vol.43 , pp. 1216-1226
    • Oldfield, E.1
  • 23
    • 0002869606 scopus 로고
    • Biosynthesis of non-head-to-tail terpenes. Formation of 1′-1 and 1′-3 linkages
    • Poulter CD. 1990. Biosynthesis of non-head-to-tail terpenes. Formation of 1′-1 and 1′-3 linkages. Acc. Chem. Res. 23:70 -77.
    • (1990) Acc. Chem. Res. , vol.23 , pp. 70-77
    • Poulter, C.D.1
  • 24
    • 4344677917 scopus 로고    scopus 로고
    • Nitrogen-containing bisphosphonate mechanism of action
    • Reszka AA, Rodan GA. 2004. Nitrogen-containing bisphosphonate mechanism of action. Mini-Rev. Med. Chem. 4:711-719. (Pubitemid 39149473)
    • (2004) Mini-Reviews in Medicinal Chemistry , vol.4 , Issue.7 , pp. 711-719
    • Reszka, A.A.1    Rodan, G.A.2
  • 27
    • 78649842994 scopus 로고    scopus 로고
    • Bisphosphonates: Molecular mechanisms of action and effects on bone cells, monocytes and macrophages
    • Roelofs AJ, Thompson K, Ebetino FH, Rogers MJ, Coxon FP. 2010. Bisphosphonates: molecular mechanisms of action and effects on bone cells, monocytes and macrophages. Curr. Pharm. Des. 16:2950-2960.
    • (2010) Curr. Pharm. Des. , vol.16 , pp. 2950-2960
    • Roelofs, A.J.1    Thompson, K.2    Ebetino, F.H.3    Rogers, M.J.4    Coxon, F.P.5
  • 29
    • 79953227657 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of New 2-alkylaminoethyl-1,1- bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase
    • Rosso VS, et al. 2011. Synthesis and biological evaluation of New 2-alkylaminoethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase. Bioorg. Med. Chem. 19:2211-2217.
    • (2011) Bioorg. Med. Chem. , vol.19 , pp. 2211-2217
    • Rosso, V.S.1
  • 30
    • 0033065233 scopus 로고    scopus 로고
    • Bisphosphonates: From the laboratory to the clinic and back again
    • DOI 10.1016/S8756-3282(99)00116-7, PII S8756328299001167
    • Russell RGG, Rogers MJ. 1999. Bisphosphonates: from the laboratory to the clinic and back again. Bone 25:97-106. (Pubitemid 29322070)
    • (1999) Bone , vol.25 , Issue.1 , pp. 97-106
    • Russell, R.G.G.1    Rogers, M.J.2
  • 32
    • 84863012657 scopus 로고    scopus 로고
    • Design, synthesis and biological evaluation of 1-(fluoroalkylidene)-1,1- bisphosphonic acids against Toxoplasma gondii targeting farnesyl diphosphate synthase
    • Szajnman SH, et al. 2012. Design, synthesis and biological evaluation of 1-(fluoroalkylidene)-1,1-bisphosphonic acids against Toxoplasma gondii targeting farnesyl diphosphate synthase. Org. Biomol. Chem. 10:1424-1433.
    • (2012) Org. Biomol. Chem. , vol.10 , pp. 1424-1433
    • Szajnman, S.H.1
  • 34
    • 25444525132 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of 1-amino-1,1-bisphosphonates derived from fatty acids against Trypanosoma cruzi targeting farnesyl pyrophosphate synthase
    • Szajnman SH, Ravaschino EL, Docampo R, Rodriguez JB. 2005. Synthesis and biological evaluation of 1-amino-1,1-bisphosphonates derived from fatty acids against Trypanosoma cruzi targeting farnesyl pyrophosphate synthase. Bioorg. Med. Chem. Lett. 15:4685- 4690.
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 4685-4690
    • Szajnman, S.H.1    Ravaschino, E.L.2    Docampo, R.3    Rodriguez, J.B.4
  • 35
    • 0041330424 scopus 로고    scopus 로고
    • Bisphosphonates derived from fatty acids are potent inhibitors of Trypanosoma cruzi farnesyl pyrophosphate synthase
    • DOI 10.1016/S0960-894X(03)00663-2
    • Szajnman SH, Montalvetti A, Wang Y, Docampo R, Rodriguez JB. 2003. Bisphosphonates derived from fatty acids are potent inhibitors of Trypanosoma cruzi farnesyl pyrophosphate synthase. Bioorg. Med. Chem. Lett. 13:3231-3235. (Pubitemid 37093834)
    • (2003) Bioorganic and Medicinal Chemistry Letters , vol.13 , Issue.19 , pp. 3231-3235
    • Szajnman, S.H.1    Montalvetti, A.2    Wang, Y.3    Docampo, R.4    Rodriguez, J.B.5
  • 36
    • 0035953026 scopus 로고    scopus 로고
    • Bisphosphonates derived from fatty acids are potent growth inhibitors of Trypanosoma cruzi
    • Szajnman SH, Bailey BN, Docampo R, Rodriguez JB. 2001. Bisphosphonates derived from fatty acids are potent growth inhibitors of Trypanosoma cruzi. Bioorg. Med. Chem. Lett. 11:789 -792.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 789-792
    • Szajnman, S.H.1    Bailey, B.N.2    Docampo, R.3    Rodriguez, J.B.4
  • 37
    • 77953082627 scopus 로고    scopus 로고
    • Specific chemotherapy of Chagas disease: Relevance, current limitations and new approaches
    • Urbina JA. 2010. Specific chemotherapy of Chagas disease: relevance, current limitations and new approaches. Acta Trop. 115:55- 68.
    • (2010) Acta Trop. , vol.115 , pp. 55-68
    • Urbina, J.A.1
  • 38
    • 77955436769 scopus 로고    scopus 로고
    • New insights in Chagas' disease treatment
    • Urbina JA. 2010. New insights in Chagas' disease treatment. Drugs Fut. 35:409-420.
    • (2010) Drugs Fut. , vol.35 , pp. 409-420
    • Urbina, J.A.1
  • 39
    • 0033585003 scopus 로고    scopus 로고
    • Trypanosoma cruzi contains major pyrophosphate stores, and its growth in vitro and in vivo is blocked by pyrophosphate analogs
    • Urbina JA, et al. 1999. Trypanosoma cruzi contains major pyrophosphate stores, and its growth in vitro and in vivo is blocked by pyrophosphate analogs. J. Biol. Chem. 274:33609 -33615.
    • (1999) J. Biol. Chem. , vol.274 , pp. 33609-33615
    • Urbina, J.A.1
  • 40
    • 0142227145 scopus 로고    scopus 로고
    • Specific chemotherapy of Chagas disease: Controversies and advances
    • DOI 10.1016/j.pt.2003.09.001
    • Urbina JA, Docampo R. 2003. Specific chemotherapy of Chagas' disease: controversies and advances. Trends Parasitol. 19:495-501. (Pubitemid 37329658)
    • (2003) Trends in Parasitology , vol.19 , Issue.11 , pp. 495-501
    • Urbina, J.A.1    Docampo, R.2
  • 41
    • 0036171419 scopus 로고    scopus 로고
    • In vivo activities of farnesyl pyrophosphate synthase inhibitors against Leishmania donovani and Toxoplasma gondii
    • Yardley V, et al. 2002. In vivo activities of farnesyl pyrophosphate synthase inhibitors against Leishmania donovani and Toxoplasma gondii. Antimicrob. Agents Chemother. 46:929 -931.
    • (2002) Antimicrob. Agents Chemother. , vol.46 , pp. 929-931
    • Yardley, V.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.