메뉴 건너뛰기




Volumn 1830, Issue 6, 2013, Pages 3635-3642

Multi-target-directed design, syntheses, and characterization of fluorescent bisphosphonate derivatives as multifunctional enzyme inhibitors in mevalonate pathway

Author keywords

Bisphosphonate; Farnesyl pyrophosphate synthase; Mevalonate 5 diphosphate decarboxylase; Mevalonate kinase; Multifunctional inhibitor; Phosphomevalonate kinase

Indexed keywords

2 (15 CARBOXY 15 FLUORO 14 HYDROXY 2,6,14 TRIMETHYL 9,9 DIPHOSPHONOPENTADECA 2,6 DIENYLAMINO)BENZOIC ACID; 2 (15 CARBOXY 15,15 DIFLUORO 14 HYDROXY 2,6,14 TRIMETHYL 9,9 DIPHOSPHONOPENTADECA 2,6 DIENYLAMINO)BENZOIC ACID; BISPHOSPHONIC ACID DERIVATIVE; CARBOXYLYASE; DIPHOSPHOMEVALONATE DECARBOXYLASE; ENZYME INHIBITOR; GERANYLTRANSFERASE; MEVALONATE KINASE; PHOSPHOMEVALONATE KINASE; UNCLASSIFIED DRUG;

EID: 84875973434     PISSN: 03044165     EISSN: 18728006     Source Type: Journal    
DOI: 10.1016/j.bbagen.2013.02.011     Document Type: Article
Times cited : (15)

References (34)
  • 1
    • 34249685010 scopus 로고    scopus 로고
    • Mevalonate pathway: A review of clinical and therapeutical implications
    • I. Buhaescu, and H. Izzedine Mevalonate pathway: a review of clinical and therapeutical implications Clin. Biochem. 40 2007 575 584
    • (2007) Clin. Biochem. , vol.40 , pp. 575-584
    • Buhaescu, I.1    Izzedine, H.2
  • 3
    • 33644858461 scopus 로고    scopus 로고
    • Anti-cancer therapy: Targeting the mevalonate pathway
    • K.M. Swanson, and R.J. Hohl Anti-cancer therapy: targeting the mevalonate pathway Curr. Cancer Drug Targets 6 2006 15 37
    • (2006) Curr. Cancer Drug Targets , vol.6 , pp. 15-37
    • Swanson, K.M.1    Hohl, R.J.2
  • 4
    • 77956975241 scopus 로고    scopus 로고
    • Targeting isoprenoid biosynthesis for drug discovery: Bench to bedside
    • E. Oldfield Targeting isoprenoid biosynthesis for drug discovery: bench to bedside Acc. Chem. Res. 43 2010 1216 1226
    • (2010) Acc. Chem. Res. , vol.43 , pp. 1216-1226
    • Oldfield, E.1
  • 5
    • 0025120211 scopus 로고
    • Regulation of the mevalonate pathway
    • J.L. Goldstein, and M.S. Brown Regulation of the mevalonate pathway Nature 343 1990 425
    • (1990) Nature , vol.343 , pp. 425
    • Goldstein, J.L.1    Brown, M.S.2
  • 8
    • 84859804837 scopus 로고    scopus 로고
    • Design and synthesis of active site inhibitors of the human farnesyl pyrophosphate synthase: Apoptosis and inhibition of ERK phosphorylation in multiple myeloma cells
    • Y.S. Lin, J. Park, J.W. De Schutter, X.F. Huang, A.M. Berghuis, M. Sebag, and Y.S. Tsantrizos Design and synthesis of active site inhibitors of the human farnesyl pyrophosphate synthase: apoptosis and inhibition of ERK phosphorylation in multiple myeloma cells J. Med. Chem. 55 2012 3201 3215
    • (2012) J. Med. Chem. , vol.55 , pp. 3201-3215
    • Lin, Y.S.1    Park, J.2    De Schutter, J.W.3    Huang, X.F.4    Berghuis, A.M.5    Sebag, M.6    Tsantrizos, Y.S.7
  • 9
    • 79955628599 scopus 로고    scopus 로고
    • Design, synthesis, and characterization of piperazinedione-based dual protein inhibitors for both farnesyltransferase and geranylgeranyltransferase-I
    • Y. Qiao, J. Gao, Y. Qiu, L. Wu, F. Guo, K.K. Lo, and D. Li Design, synthesis, and characterization of piperazinedione-based dual protein inhibitors for both farnesyltransferase and geranylgeranyltransferase-I Eur. J. Med. Chem. 46 2011 2264 2273
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 2264-2273
    • Qiao, Y.1    Gao, J.2    Qiu, Y.3    Wu, L.4    Guo, F.5    Lo, K.K.6    Li, D.7
  • 11
    • 35748962429 scopus 로고    scopus 로고
    • The safety of statins in clinical practice
    • J. Armitage The safety of statins in clinical practice Lancet 370 2007 1781 1790
    • (2007) Lancet , vol.370 , pp. 1781-1790
    • Armitage, J.1
  • 13
    • 59749088584 scopus 로고    scopus 로고
    • Clinical review: Bisphosphonate use in childhood osteoporosis
    • L.K. Bachrach, and L.M. Ward Clinical review: bisphosphonate use in childhood osteoporosis J. Clin. Endocrinol. Metab. 94 2009 400 409
    • (2009) J. Clin. Endocrinol. Metab. , vol.94 , pp. 400-409
    • Bachrach, L.K.1    Ward, L.M.2
  • 14
    • 61849099801 scopus 로고    scopus 로고
    • Safety and efficacy of intravenous zoledronic acid in paediatric osteoporosis
    • J. Brown, and M. Zacharin Safety and efficacy of intravenous zoledronic acid in paediatric osteoporosis J. Pediatr. Endocrinol. Metab. 22 2009 55 64
    • (2009) J. Pediatr. Endocrinol. Metab. , vol.22 , pp. 55-64
    • Brown, J.1    Zacharin, M.2
  • 16
    • 0031803315 scopus 로고    scopus 로고
    • Treatment of osteoporosis with bisphosphonates
    • N.B. Watts Treatment of osteoporosis with bisphosphonates Endocrinol. Metab. Clin. 27 1998 419 439
    • (1998) Endocrinol. Metab. Clin. , vol.27 , pp. 419-439
    • Watts, N.B.1
  • 17
    • 0032406920 scopus 로고    scopus 로고
    • The role of bisphosphonates in the treatment of painful metastatic bone disease: A review of phase III trials
    • F. Fulfaro, A. Casuccio, C. Ticozzi, and C. Ripamonti The role of bisphosphonates in the treatment of painful metastatic bone disease: a review of phase III trials Pain 78 1998 157 169
    • (1998) Pain , vol.78 , pp. 157-169
    • Fulfaro, F.1    Casuccio, A.2    Ticozzi, C.3    Ripamonti, C.4
  • 18
    • 33846615517 scopus 로고    scopus 로고
    • Synthesis of fluorescently tagged isoprenoid bisphosphonates that inhibit protein geranylgeranylation
    • M.A. Maalouf, A.J. Wiemer, C.H. Kuder, R.J. Hohl, and D.F. Wiemer Synthesis of fluorescently tagged isoprenoid bisphosphonates that inhibit protein geranylgeranylation Bioorg. Med. Chem. 15 2007 1959 1966
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 1959-1966
    • Maalouf, M.A.1    Wiemer, A.J.2    Kuder, C.H.3    Hohl, R.J.4    Wiemer, D.F.5
  • 19
    • 0347298751 scopus 로고    scopus 로고
    • Synthesis and application of a fluorescent substrate analogue to study ligand interactions for undecaprenyl pyrophosphate synthase
    • A.P.C. Chen, Y.H. Chen, H.P. Liu, Y.C. Li, C.T. Chen, and P.H. Liang Synthesis and application of a fluorescent substrate analogue to study ligand interactions for undecaprenyl pyrophosphate synthase J. Am. Chem. Soc. 124 2002 15217 15224
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 15217-15224
    • Chen, A.P.C.1    Chen, Y.H.2    Liu, H.P.3    Li, Y.C.4    Chen, C.T.5    Liang, P.H.6
  • 20
    • 77954755647 scopus 로고    scopus 로고
    • Discovery of potent inhibitor for farnesyl pyrophosphate synthase in the mevalonate pathway
    • J. Gao, X. Chu, Y. Qiu, L. Wu, Y. Qiao, J. Wu, and D. Li Discovery of potent inhibitor for farnesyl pyrophosphate synthase in the mevalonate pathway Chem. Commun. 46 2010 5340 5342
    • (2010) Chem. Commun. , vol.46 , pp. 5340-5342
    • Gao, J.1    Chu, X.2    Qiu, Y.3    Wu, L.4    Qiao, Y.5    Wu, J.6    Li, D.7
  • 21
    • 33744972306 scopus 로고    scopus 로고
    • Inhibition of mevalonate 5-diphosphate decarboxylase by fluorinated substrate analogs
    • Y. Qiu, and D. Li Inhibition of mevalonate 5-diphosphate decarboxylase by fluorinated substrate analogs Biochim. Biophys. Acta 1760 2006 1080 1087
    • (2006) Biochim. Biophys. Acta , vol.1760 , pp. 1080-1087
    • Qiu, Y.1    Li, D.2
  • 22
    • 0043142179 scopus 로고    scopus 로고
    • Cloning, expression, and purification of His-tagged rat mevalonate kinase
    • X. Chu, and D. Li Cloning, expression, and purification of His-tagged rat mevalonate kinase Protein Expression Purif. 27 2003 165 170
    • (2003) Protein Expression Purif. , vol.27 , pp. 165-170
    • Chu, X.1    Li, D.2
  • 23
    • 0345211538 scopus 로고    scopus 로고
    • Microplate enzyme-coupled assays of mevalonate and phosphomevalonate kinase from Catharanthus roseus suspension cultured cells
    • A.E. Schulte, R. van der Heijden, and R. Verpoorte Microplate enzyme-coupled assays of mevalonate and phosphomevalonate kinase from Catharanthus roseus suspension cultured cells Anal. Biochem. 269 1999 245 254
    • (1999) Anal. Biochem. , vol.269 , pp. 245-254
    • Schulte, A.E.1    Van Der Heijden, R.2    Verpoorte, R.3
  • 24
    • 20444483335 scopus 로고    scopus 로고
    • A dendritic tetra(bisphosphonic acid) for improved targeting of proteins to bone
    • G. Bansal, J.E.I. Wright, C. Kucharski, and H. Uludag A dendritic tetra(bisphosphonic acid) for improved targeting of proteins to bone Angew. Chem. Int. Ed. 44 2005 3710 3714
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 3710-3714
    • Bansal, G.1    Wright, J.E.I.2    Kucharski, C.3    Uludag, H.4
  • 27
    • 0037314783 scopus 로고    scopus 로고
    • An intuitive look at the relationship of Ki and IC50: A more general use for the Dixon plot
    • B.T. Burlingham, and T.S. Widlanski An intuitive look at the relationship of Ki and IC50: a more general use for the Dixon plot J. Chem. Educ. 80 2003 214
    • (2003) J. Chem. Educ. , vol.80 , pp. 214
    • Burlingham, B.T.1    Widlanski, T.S.2
  • 28
  • 31
    • 20044389681 scopus 로고    scopus 로고
    • Bisphosphonates in breast cancer
    • R. Coleman Bisphosphonates in breast cancer Ann. Oncol. 16 2005 687 695
    • (2005) Ann. Oncol. , vol.16 , pp. 687-695
    • Coleman, R.1
  • 32
    • 0037304115 scopus 로고    scopus 로고
    • Antitumor effects of bisphosphonates
    • J.R. Green Antitumor effects of bisphosphonates Cancer 97 2003 840 847
    • (2003) Cancer , vol.97 , pp. 840-847
    • Green, J.R.1
  • 34
    • 58149104159 scopus 로고    scopus 로고
    • Bisphosphonate inhibition of a plasmodium farnesyl diphosphate synthase and a general method for predicting cell-based activity from enzyme data
    • D. Mukkamala, J.H. No, L.M. Cass, T.K. Chang, and E. Oldfield Bisphosphonate inhibition of a plasmodium farnesyl diphosphate synthase and a general method for predicting cell-based activity from enzyme data J. Med. Chem. 51 2008 7827 7833
    • (2008) J. Med. Chem. , vol.51 , pp. 7827-7833
    • Mukkamala, D.1    No, J.H.2    Cass, L.M.3    Chang, T.K.4    Oldfield, E.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.