메뉴 건너뛰기




Volumn 1840, Issue 3, 2014, Pages 1051-1062

Syntheses and characterization of non-bisphosphonate quinoline derivatives as new FPPS inhibitors

Author keywords

Allosteric site; Bisphosphonate; Cancer; Farnesyl pyrophosphate synthase; Quinoline derivative

Indexed keywords

((4 CHLOROBENZO[H]QUINOLIN 2 YL)METHYL)PHOSPHONIC ACID; 2 ((2 ((2 CARBOXYPHENOXY)METHYL)QUINOLIN 4 YL)AMINO)BENZOIC ACID; 2 ((2 (CHLOROMETHYL)QUINOLIN 4 YL)AMINO)BENZOIC ACID; 2 ((2 METHYLBENZO[H]QUINOLIN 4 YL)AMINO)BENZOIC ACID; 2 ((4 CHLOROBENZO[H]QUINOLIN 2 YL)METHOXY)BENZOIC ACID; 2 ((4 CHLOROBENZO[H]QUINOLIN 2 YL)METHYL)MALONIC ACID; 2 ((4 CHLOROQUINOLIN 2 YL)METHOXY)BENZOIC ACID; 3 (4 CHLOROBENZO[H]QUINOLIN 2 YL) 2 PHOSPHONOPROPANOIC ACID; 4 CHLORO 2 ((4 ((4 METHOXYPHENYL)AMINO)BENZO[H]QUINOLIN 2 YL)METHOXY)BENZOIC ACID; 5 ((2 ((2 CARBOXYPHENOXY)METHYL)BENZO[H]QUINOLIN 4 YL)AMINO)ISOPHTHALIC ACID; ANTINEOPLASTIC AGENT; DIETHYL ((4 CHLOROBENZO[H]QUINOLIN 2 YL)METHYL)PHOSPHONATE; DIMETHYL 2 ((4 CHLOROBENZO[H]QUINOLIN 2 YL)METHYL)MALONATE; DIMETHYL 5 ((2 ((2 (ETHOXYCARBONYL)PHENOXY)METHYL)BENZO[H]QUINOLIN 4 YL)AMINO)ISOPHTHALATE; ETHYL 2 ((4 ((2 (METHOXYCARBONYL)PHENYL)AMINO)QUINOLIN 2 YL)METHOXY)BENZOATE; ETHYL 2 ((4 CHLOROBENZO[H]QUINOLIN 2 YL)METHOXY)BENZOATE; ETHYL 2 ((4 CHLOROQUINOLIN 2 YL)METHOXY)BENZOATE; ETHYL 3 (4 CHLOROBENZO[H]QUINOLIN 2 YL) 2(DIETHOXYPHOSPHORYL)PROPANOATE; GERANYLTRANSFERASE; HYDROXYAPATITE; METHYL 2 ((2 (CHLOROMETHYL)QUINOLIN 4 YL)AMINO)BENZOATE; METHYL 2 (2 METHYLBENZO[H]QUINOLIN 4 YLAMINO)BENZOATE; METHYL 4 CHLORO 2 ((4 ((4 METHOXYPHENYL)AMINO)BENZO[H]QUINOLIN 2 YL)METHOXY)BENZOATE; QUINOLINE DERIVATIVE; TRANSFERASE INHIBITOR; UNCLASSIFIED DRUG; ZOLEDRONIC ACID;

EID: 84890463727     PISSN: 03044165     EISSN: 18728006     Source Type: Journal    
DOI: 10.1016/j.bbagen.2013.11.006     Document Type: Article
Times cited : (16)

References (37)
  • 1
    • 0032942599 scopus 로고    scopus 로고
    • Bisphosphonates: Pharmacology, mechanisms of action and clinical uses
    • R. Russell, P. Croucher, and M. Rogers Bisphosphonates: pharmacology, mechanisms of action and clinical uses Osteoporos. Int. 9 1999 S66 S80
    • (1999) Osteoporos. Int. , vol.9
    • Russell, R.1    Croucher, P.2    Rogers, M.3
  • 2
    • 10644231736 scopus 로고    scopus 로고
    • The role of bisphosphonates in breast cancer
    • R.E. Coleman The role of bisphosphonates in breast cancer Breast 13 Suppl. 1 2004 S19 S28
    • (2004) Breast , vol.13 , Issue.SUPPL. 1
    • Coleman, R.E.1
  • 3
    • 80052075924 scopus 로고    scopus 로고
    • Farnesyl pyrophosphate synthase modulators: A patent review (2006-2010)
    • S. Sun, and C.E. McKenna Farnesyl pyrophosphate synthase modulators: a patent review (2006-2010) Expert. Opin. Ther. Pat. 21 2011 1433 1451
    • (2011) Expert. Opin. Ther. Pat. , vol.21 , pp. 1433-1451
    • Sun, S.1    McKenna, C.E.2
  • 4
    • 33744762777 scopus 로고    scopus 로고
    • Bisphosphonates: From bench to bedside
    • DOI 10.1196/annals.1346.041
    • R.G.G. Russell Bisphosphonates: from bench to bedside Ann. N. Y. Acad. Sci. 1068 2006 367 401 (Pubitemid 43824169)
    • (2006) Annals of the New York Academy of Sciences , vol.1068 , Issue.1 , pp. 367-401
    • Russell, R.G.G.1
  • 5
    • 79955042489 scopus 로고    scopus 로고
    • Bisphosphonates induce autophagy by depleting geranylgeranyl diphosphate
    • B.M. Wasko, A. Dudakovic, and R.J. Hohl Bisphosphonates induce autophagy by depleting geranylgeranyl diphosphate J. Pharmacol. Exp. Ther. 337 2011 540 546
    • (2011) J. Pharmacol. Exp. Ther. , vol.337 , pp. 540-546
    • Wasko, B.M.1    Dudakovic, A.2    Hohl, R.J.3
  • 6
    • 5444242637 scopus 로고    scopus 로고
    • Bisphosphonates: Preclinical review
    • J.R. Green Bisphosphonates: preclinical review Oncologist 9 2004 3 13 (Pubitemid 39363164)
    • (2004) Oncologist , vol.9 , Issue.SUPPL. 4 , pp. 3-13
    • Green, J.R.1
  • 8
    • 0034819685 scopus 로고    scopus 로고
    • Differentiation between conformational and autoproteolytic stability of the neutral protease from Bacillus stearothermophilus containing an engineered disulfide bond
    • DOI 10.1046/j.1432-1327.2001.02270.x
    • P. Dürrschmidt, J. Mansfeld, and R. Ulbrich-Hofmann Differentiation between conformational and autoproteolytic stability of the neutral protease from Bacillus stearothermophilus containing an engineered disulfide bond Eur. J. Biochem. 268 2001 3612 3618 (Pubitemid 32862955)
    • (2001) European Journal of Biochemistry , vol.268 , Issue.12 , pp. 3612-3618
    • Durrschmidt, P.1    Mansfeld, J.2    Ulbrich-Hofmann, R.3
  • 9
    • 80052663778 scopus 로고    scopus 로고
    • Identification of a lysine residue important for the catalytic activity of yeast farnesyl diphosphate synthase
    • M.J. Fischer, S. Meyer, P. Claudel, M. Bergdoll, and F. Karst Identification of a lysine residue important for the catalytic activity of yeast farnesyl diphosphate synthase Protein J. 30 2011 334 339
    • (2011) Protein J. , vol.30 , pp. 334-339
    • Fischer, M.J.1    Meyer, S.2    Claudel, P.3    Bergdoll, M.4    Karst, F.5
  • 13
    • 34648828862 scopus 로고    scopus 로고
    • Bisphosphonates in cancer therapy
    • DOI 10.1016/j.canlet.2007.07.007, PII S0304383507002972
    • V. Stresing, F. Daubiné, I. Benzaid, H. Mönkkönen, and P. Clézardin Bisphosphonates in cancer therapy Cancer Lett. 257 2007 16 35 (Pubitemid 47464698)
    • (2007) Cancer Letters , vol.257 , Issue.1 , pp. 16-35
    • Stresing, V.1    Daubine, F.2    Benzaid, I.3    Monkkonen, H.4    Clezardin, P.5
  • 14
    • 77950994646 scopus 로고    scopus 로고
    • Autophagy: Cellular and molecular mechanisms
    • D. Glick, S. Barth, and K.F. Macleod Autophagy: cellular and molecular mechanisms J. Pathol. 221 2010 3 12
    • (2010) J. Pathol. , vol.221 , pp. 3-12
    • Glick, D.1    Barth, S.2    Macleod, K.F.3
  • 16
    • 55349135188 scopus 로고    scopus 로고
    • Lowering bone mineral affinity of bisphosphonates as a therapeutic strategy to optimize skeletal tumor growth inhibition in vivo
    • P.G. Fournier, F. Daubine, M.W. Lundy, M.J. Rogers, F.H. Ebetino, and P. Clezardin Lowering bone mineral affinity of bisphosphonates as a therapeutic strategy to optimize skeletal tumor growth inhibition in vivo Cancer Res. 68 2008 8945 8953
    • (2008) Cancer Res. , vol.68 , pp. 8945-8953
    • Fournier, P.G.1    Daubine, F.2    Lundy, M.W.3    Rogers, M.J.4    Ebetino, F.H.5    Clezardin, P.6
  • 18
    • 52249106627 scopus 로고    scopus 로고
    • Structures of a potent phenylalkyl bisphosphonate inhibitor bound to farnesyl and geranylgeranyl diphosphate synthases
    • R. Cao, C.K. Chen, R.T. Guo, A.H. Wang, and E. Oldfield Structures of a potent phenylalkyl bisphosphonate inhibitor bound to farnesyl and geranylgeranyl diphosphate synthases Proteins 73 2008 431 439
    • (2008) Proteins , vol.73 , pp. 431-439
    • Cao, R.1    Chen, C.K.2    Guo, R.T.3    Wang, A.H.4    Oldfield, E.5
  • 19
    • 37849026761 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of r -halogenated bisphosphonate and phosphonocarboxylate analogues of risedronate
    • M.S. Marma, Z. Xia, C. Stewart, F. Coxon, and J.E. Dunford Synthesis and biological evaluation of r -halogenated bisphosphonate and phosphonocarboxylate analogues of risedronate J. Med. Chem. 50 2007 9
    • (2007) J. Med. Chem. , vol.50 , pp. 9
    • Marma, M.S.1    Xia, Z.2    Stewart, C.3    Coxon, F.4    Dunford, J.E.5
  • 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. (Camb.) 46 2010 5340 5342
    • (2010) Chem. Commun. (Camb.) , 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
    • 84875973434 scopus 로고    scopus 로고
    • Multi-target-directed design, syntheses, and characterization of fluorescent bisphosphonate derivatives as multifunctional enzyme inhibitors in mevalonate pathway
    • J. Gao, J. Liu, Y. Qiu, X. Chu, Y. Qiao, and D. Li Multi-target-directed design, syntheses, and characterization of fluorescent bisphosphonate derivatives as multifunctional enzyme inhibitors in mevalonate pathway Biochim. Biophys. Acta Gen. Subj. 1830 2013 3635 3642
    • (2013) Biochim. Biophys. Acta Gen. Subj. , vol.1830 , pp. 3635-3642
    • Gao, J.1    Liu, J.2    Qiu, Y.3    Chu, X.4    Qiao, Y.5    Li, D.6
  • 23
    • 84855834894 scopus 로고    scopus 로고
    • Highly efficient thermal cyclization reactions of alkylidene esters in continuous flow to give aromatic/heteroaromatic derivatives
    • L. Lengyel, T.Z. Nagy, G. Sipos, R. Jones, G. Dormán, L. Ürge, and F. Darvas Highly efficient thermal cyclization reactions of alkylidene esters in continuous flow to give aromatic/heteroaromatic derivatives Tetrahedron Lett. 53 2012 738 743
    • (2012) Tetrahedron Lett. , vol.53 , pp. 738-743
    • Lengyel, L.1    Nagy, T.Z.2    Sipos, G.3    Jones, R.4    Dormán, G.5    Ürge, L.6    Darvas, F.7
  • 24
    • 77952822942 scopus 로고    scopus 로고
    • Convenient and Efficient microwave-assisted synthesis of a methyl derivative of the fused indoloquinoline alkaloid cryptosanguinolentine
    • R.M. Gengan, P. Pandian, C. Kumarsamy, and P.S. Mohan Convenient and Efficient microwave-assisted synthesis of a methyl derivative of the fused indoloquinoline alkaloid cryptosanguinolentine Molecules 15 2010 3171 3178
    • (2010) Molecules , vol.15 , pp. 3171-3178
    • Gengan, R.M.1    Pandian, P.2    Kumarsamy, C.3    Mohan, P.S.4
  • 25
    • 36148940978 scopus 로고    scopus 로고
    • Synthesis of 6, 8-substituted 4-(hydroxyphenylamino)-and 4-(aminophenylamino)-2-methylquinolines
    • A. Avetisyan, I. Aleksanyan, and L. Ambartsumyan Synthesis of 6, 8-substituted 4-(hydroxyphenylamino)-and 4-(aminophenylamino)-2-methylquinolines Russ. J. Org. Chem. 43 2007 1048 1051
    • (2007) Russ. J. Org. Chem. , vol.43 , pp. 1048-1051
    • Avetisyan, A.1    Aleksanyan, I.2    Ambartsumyan, L.3
  • 26
    • 33748794547 scopus 로고    scopus 로고
    • Theoretical basis, experimental design, and computerized simulation of synergism and antagonism in drug combination studies
    • T.C. Chou Theoretical basis, experimental design, and computerized simulation of synergism and antagonism in drug combination studies Pharmacol. Rev. 58 2006 621 681
    • (2006) Pharmacol. Rev. , vol.58 , pp. 621-681
    • Chou, T.C.1
  • 27
    • 76549129820 scopus 로고    scopus 로고
    • Drug combination studies and their synergy quantification using the Chou-Talalay method
    • T.C. Chou Drug combination studies and their synergy quantification using the Chou-Talalay method Cancer Res. 70 2010 440 446
    • (2010) Cancer Res. , vol.70 , pp. 440-446
    • Chou, T.C.1
  • 28
    • 84877582640 scopus 로고    scopus 로고
    • Facile syntheses of disubstituted bis(vinylquinolinium)benzene derivatives as G-quadruplex DNA binders
    • Z.-Q. Liu, S.-T. Zhuo, J.-H. Tan, T.-M. Ou, D. Li, L.-Q. Gu, and Z.-S. Huang Facile syntheses of disubstituted bis(vinylquinolinium)benzene derivatives as G-quadruplex DNA binders Tetrahedron 69 2013 4922 4932
    • (2013) Tetrahedron , vol.69 , pp. 4922-4932
    • Liu, Z.-Q.1    Zhuo, S.-T.2    Tan, J.-H.3    Ou, T.-M.4    Li, D.5    Gu, L.-Q.6    Huang, Z.-S.7
  • 32
    • 2442715239 scopus 로고    scopus 로고
    • Thermal, chemical, and enzymatic stability of the cyclotide kalata B1: The importance of the cyclic cystine knot
    • DOI 10.1021/bi049711q
    • M.L. Colgrave, and D.J. Craik Thermal, chemical, and enzymatic stability of the cyclotide kalata B1: the importance of the cyclic cystine knot † Biochemistry 43 2004 5965 5975 (Pubitemid 38669464)
    • (2004) Biochemistry , vol.43 , Issue.20 , pp. 5965-5975
    • Colgrave, M.L.1    Craik, D.J.2
  • 33
    • 0031027122 scopus 로고    scopus 로고
    • Characterization of binding interactions by isothermal titration calorimetry
    • DOI 10.1016/S0958-1669(97)80154-1
    • M.L. Doyle Characterization of binding interactions by isothermal titration calorimetry Curr. Opin. Biotechnol. 8 1997 31 35 (Pubitemid 27075099)
    • (1997) Current Opinion in Biotechnology , vol.8 , Issue.1 , pp. 31-35
    • Doyle, M.L.1
  • 34
    • 34548400444 scopus 로고    scopus 로고
    • Energetics of quadruplex-drug recognition in anticancer therapy
    • DOI 10.2174/156800907781662257
    • B. Pagano, and C. Giancola Energetics of quadruplex-drug recognition in anticancer therapy Curr. Cancer Drug Targets 7 2007 520 540 (Pubitemid 47358140)
    • (2007) Current Cancer Drug Targets , vol.7 , Issue.6 , pp. 520-540
    • Pagano, B.1    Giancola, C.2
  • 35
    • 68949139305 scopus 로고    scopus 로고
    • Applications of isothermal titration calorimetry in biophysical studies of G-quadruplexes
    • B. Pagano, C.A. Mattia, and C. Giancola Applications of isothermal titration calorimetry in biophysical studies of G-quadruplexes Int. J. Mol. Sci. 10 2009 2935 2957
    • (2009) Int. J. Mol. Sci. , vol.10 , pp. 2935-2957
    • Pagano, B.1    Mattia, C.A.2    Giancola, C.3
  • 36
    • 77951685290 scopus 로고    scopus 로고
    • An inâ€...vitro assay to measure targeted drug delivery to bone mineral
    • W. Jahnke, and C. Henry An inâ€...vitro assay to measure targeted drug delivery to bone mineral ChemMedChem 5 2010 770 776
    • (2010) ChemMedChem , vol.5 , pp. 770-776
    • Jahnke, W.1    Henry, C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.