메뉴 건너뛰기




Volumn 55, Issue 3, 2012, Pages 1242-1251

Structure-activity relationships of cyanoquinolines with corrector-potentiator activity in Δf508 cystic fibrosis transmembrane conductance regulator protein

Author keywords

[No Author keywords available]

Indexed keywords

2 [4 (2 METHOXYBENZOYL)PIPERAZIN 1 YL] 5,7 DIMETHYLQUINOLINE 3 CARBONITRILE; 2 [4 (3 METHOXYBENZOYL)PIPERAZIN 1 YL] 5,7 DIMETHYLQUINOLINE 3 CARBONITRILE; 2 [4 (4 METHOXYBENZOYL)PIPERAZIN 1 YL] 5,7 DIMETHYLQUINOLINE 3 CARBONITRILE; 5,7 DIMETHYL 2 (4 PICOLINOYLPIPERAZIN 1 YL)QUINOLINE 3 CARBONITRILE; AROMATIC AMIDE; N [2 [(3 CYANO 5,7 DIMETHYLQUINOLIN 2 YL)AMINO]ETHYL] 2 METHOXYBENZAMIDE; N [2 [(3 CYANO 5,7 DIMETHYLQUINOLIN 2 YL)AMINO]ETHYL] 2,4 DIMETHOXYBENZAMIDE; N [2 [(3 CYANO 5,7 DIMETHYLQUINOLIN 2 YL)AMINO]ETHYL] 2,6 DIMETHOXYBENZAMIDE; N [2 [(3 CYANO 5,7 DIMETHYLQUINOLIN 2 YL)AMINO]ETHYL] 3,4 DIMETHOXYBENZAMIDE; N [2 [(3 CYANO 5,7 DIMETHYLQUINOLIN 2 YL)AMINO]ETHYL] 4 METHOXYBENZAMIDE; N [2 [(3 CYANO 5,7 DIMETHYLQUINOLIN 2 YL)AMINO]ETHYL] 5 METHOXYPICOLINAMIDE; N [2 [(3 CYANO 5,7 DIMETHYLQUINOLIN 2 YL)AMINO]ETHYL]BENZAMIDE; N [2 [(3 CYANO 5,7 DIMETHYLQUINOLIN 2 YL)AMINO]ETHYL]ISONICOTINAMIDE; N [2 [(3 CYANO 5,7 DIMETHYLQUINOLIN 2 YL)AMINO]ETHYL]NICOTINAMIDE; N [2 [(3 CYANO 5,7 DIMETHYLQUINOLIN 2 YL)AMINO]ETHYL]PICOLINAMIDE; N [3 (3 CYANO 5,7 DIMETHYLQUINOLIN 2 YLAMINO)PROPYL] 2 METHOXYBENZAMIDE; N [3 (3 CYANO 5,7 DIMETHYLQUINOLIN 2 YLAMINO)PROPYL] 3 METHOXYBENZAMIDE; N [3 (3 CYANO 5,7 DIMETHYLQUINOLIN 2 YLAMINO)PROPYL] 4 METHOXYBENZAMIDE; N [3 (3 CYANO 5,7 DIMETHYLQUINOLIN 2 YLAMINO)PROPYL]ISONICOTINAMIDE; N [3 (3 CYANO 5,7 DIMETHYLQUINOLIN 2 YLAMINO)PROPYL]NICOTINAMIDE; N [3 (3 CYANO 5,7 DIMETHYLQUINOLIN 2 YLAMINO)PROPYL]PICOLINAMIDE; QUINOLINE DERIVATIVE; TRANSMEMBRANE CONDUCTANCE REGULATOR; UNCLASSIFIED DRUG;

EID: 84856850146     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201372q     Document Type: Article
Times cited : (24)

References (46)
  • 3
    • 34249662628 scopus 로고    scopus 로고
    • Cystic fibrosis: A disease of vulnerability to airway surface dehydration
    • DOI 10.1016/j.molmed.2007.05.001, PII S1471491407000858
    • Boucher, R. C. Cystic fibrosis: a disease of vulnerability to airway surface dehydration Trends Mol. Med. 2007, 13, 231-240 (Pubitemid 46836874)
    • (2007) Trends in Molecular Medicine , vol.13 , Issue.6 , pp. 231-240
    • Boucher, R.C.1
  • 5
  • 6
    • 0032912589 scopus 로고    scopus 로고
    • Structure and function of the CFTR chloride channel
    • Sheppard, D. N.; Welsh, M. J. Structure and function of the CFTR chloride channel Physiol. Rev. 1999, 79, S23-S45
    • (1999) Physiol. Rev. , vol.79
    • Sheppard, D.N.1    Welsh, M.J.2
  • 8
    • 0036258208 scopus 로고    scopus 로고
    • Cystic fibrosis: A worldwide analysis of CFTR mutations - Correlation with incidence data and application to screening
    • DOI 10.1002/humu.10041
    • Bobadilla, J. L.; Macek, M; Fine, J. P.; Farrell, P. M. Cystic fibrosis: a worldwide analysis of CFTR mutations-correlation with incidence data and application to screening Hum. Mutat. 2002, 19, 575-606 (Pubitemid 34556480)
    • (2002) Human Mutation , vol.19 , Issue.6 , pp. 575-606
    • Bobadilla, J.L.1    Macek Jr., M.2    Fine, J.P.3    Farrell, P.M.4
  • 9
    • 0035937847 scopus 로고    scopus 로고
    • Conformational and temperature-sensitive stability defects of the Δf508 cystic fibrosis transmembrane conductance regulator in post-endoplasmic reticulum compartments
    • Sharma, M.; Benharouga, M.; Hu, W.; Lukacs, G. L. Conformational and temperature-sensitive stability defects of the ΔF508 cystic fibrosis transmembrane conductance regulator in post-endoplasmic reticulum compartments J. Biol. Chem. 2001, 276, 8942-8950
    • (2001) J. Biol. Chem. , vol.276 , pp. 8942-8950
    • Sharma, M.1    Benharouga, M.2    Hu, W.3    Lukacs, G.L.4
  • 11
    • 0033917142 scopus 로고    scopus 로고
    • Defects in processing and trafficking of the cystic fibrosis transmembrane conductance regulator
    • DOI 10.1046/j.1523-1755.2000.00921.x
    • Skach, W. R. Defects in processing and trafficking of the cystic fibrosis transmembrane conductance regulator Kidney Int. 2000, 57, 825-831 (Pubitemid 30434772)
    • (2000) Kidney International , vol.57 , Issue.3 , pp. 825-831
    • Skach, W.R.1
  • 12
    • 0026781952 scopus 로고
    • Processing of mutant cystic fibrosis transmembrane conductance regulator is temperature-sensitive
    • Denning, G. M.; Anderson, M. P.; Amara, J. F.; Marshall, J.; Smith, A. E.; Welsh, M. J. Processing of mutant cystic fibrosis transmembrane conductance regulator is temperature-sensitive Nature 1992, 358, 761-764
    • (1992) Nature , vol.358 , pp. 761-764
    • Denning, G.M.1    Anderson, M.P.2    Amara, J.F.3    Marshall, J.4    Smith, A.E.5    Welsh, M.J.6
  • 13
    • 0028559511 scopus 로고
    • Conformational maturation of CFTR but not its mutant counterpart (ΔF508) occurs in the endoplasmic reticulum and requires ATP
    • Lukacs, G. L.; Mohamed, A.; Kartner, N.; Chang, X.-B.; Riordan, J. R.; Grinstein, S. Conformational maturation of CFTR but not its mutant counterpart (ΔF508) occurs in the endoplasmic reticulum and requires ATP EMBO J. 1994, 13, 6076-6086
    • (1994) EMBO J. , vol.13 , pp. 6076-6086
    • Lukacs, G.L.1    Mohamed, A.2    Kartner, N.3    Chang, X.-B.4    Riordan, J.R.5    Grinstein, S.6
  • 14
    • 0032957204 scopus 로고    scopus 로고
    • Biosynthesis and degradation of CFTR
    • Kopito, R. R. Biosynthesis and degradation of CFTR Physiol. Rev. 1999, 79, S167-S173
    • (1999) Physiol. Rev. , vol.79
    • Kopito, R.R.1
  • 15
    • 11444266284 scopus 로고    scopus 로고
    • The ΔF508 cystic fibrosis mutation impairs domain-domain interactions and arrests post-translational folding of CFTR
    • DOI 10.1038/nsmb882
    • Du, K.; Sharma, M.; Lukacs, G. L. The ΔF508 cystic fibrosis mutation impairs domain-domain interactions and arrests post-translational folding of CFTR Nat. Struct. Mol. Biol. 2005, 12, 17-25 (Pubitemid 40082912)
    • (2005) Nature Structural and Molecular Biology , vol.12 , Issue.1 , pp. 17-25
    • Du, K.1    Sharma, M.2    Lukacs, G.L.3
  • 16
    • 50649123290 scopus 로고    scopus 로고
    • CFTR function and prospects for therapy
    • Riordan, J. R. CFTR function and prospects for therapy Annu. Rev. Biochem. 2008, 77, 701-726
    • (2008) Annu. Rev. Biochem. , vol.77 , pp. 701-726
    • Riordan, J.R.1
  • 18
    • 41849133213 scopus 로고    scopus 로고
    • 4′-Methyl-4,5′-bithiazole-based correctors of defective ΔF508-CFTR cellular processing
    • DOI 10.1016/j.bmcl.2008.03.037, PII S0960894X08003089
    • Yoo, C. L.; Yu, G. J.; Yang, B.; Robins, L. I.; Verkman, A. S.; Kurth, M. J. 4′-Methyl-4,5′-bithiazole-based correctors of defective ΔF508-CFTR cellular processing Bioorg. Med. Chem. Lett. 2008, 18, 2610-2614 (Pubitemid 351503887)
    • (2008) Bioorganic and Medicinal Chemistry Letters , vol.18 , Issue.8 , pp. 2610-2614
    • Yoo, C.L.1    Yu, G.J.2    Yang, B.3    Robins, L.I.4    Verkman, A.S.5    Kurth, M.J.6
  • 19
    • 53549097399 scopus 로고    scopus 로고
    • Potent s-cis-Locked Bithiazole Correctors of Δf508 Cystic Fibrosis Transmembrane Conductance Regulator Cellular Processing for Cystic Fibrosis Therapy
    • Yu, G. J.; Yoo, C. L.; Yang, B.; Lodewyk, M. W.; Meng, L.; El-Idreesy, T. T.; Fettinger, J. C.; Tantillo, D. J.; Verkman, A. S.; Kurth, M. J. Potent s-cis-Locked Bithiazole Correctors of ΔF508 Cystic Fibrosis Transmembrane Conductance Regulator Cellular Processing for Cystic Fibrosis Therapy J. Med. Chem. 2008, 51, 6044-6054
    • (2008) J. Med. Chem. , vol.51 , pp. 6044-6054
    • Yu, G.J.1    Yoo, C.L.2    Yang, B.3    Lodewyk, M.W.4    Meng, L.5    El-Idreesy, T.T.6    Fettinger, J.C.7    Tantillo, D.J.8    Verkman, A.S.9    Kurth, M.J.10
  • 20
    • 77952018949 scopus 로고    scopus 로고
    • Pyrazolylthiazole as Δf508-Cystic Fibrosis Transmembrane Conductance Regulator Correctors with Improved Hydrophilicity Compared to Bithiazoles
    • Ye, L.; Knapp, J. M.; Sangwung, P.; Fettinger, J. C.; Verkman, A. S.; Kurth, M. J. Pyrazolylthiazole as ΔF508-Cystic Fibrosis Transmembrane Conductance Regulator Correctors with Improved Hydrophilicity Compared to Bithiazoles J. Med. Chem. 2010, 53, 3772-3781
    • (2010) J. Med. Chem. , vol.53 , pp. 3772-3781
    • Ye, L.1    Knapp, J.M.2    Sangwung, P.3    Fettinger, J.C.4    Verkman, A.S.5    Kurth, M.J.6
  • 22
    • 44249097535 scopus 로고    scopus 로고
    • Parallel improvement of sodium and chloride transport defects by miglustat (n-butyldeoxynojyrimicin) in cystic fibrosis epithelial cells
    • DOI 10.1124/jpet.107.135582
    • Noel, S.; Wilke, M.; Bot, A. G.; De Jonge, H. R.; Becq, F. Parallel improvement of sodium and chloride transport defects by miglustat (n -butyldeoxynojyrimicin) in cystic fibrosis epithelial cells J. Pharmacol. Exp. Ther. 2008, 325, 1016-1023 (Pubitemid 351724326)
    • (2008) Journal of Pharmacology and Experimental Therapeutics , vol.325 , Issue.3 , pp. 1016-1023
    • Noel, S.1    Wilke, M.2    Bot, A.G.M.3    De Jonge, H.R.4    Becq, F.5
  • 24
    • 79955368563 scopus 로고    scopus 로고
    • Dual activity of aminoarylthiazoles on the trafficking and gating defects of the cystic fibrosis transmembrane conductance regulator chloride channel caused by cystic fibrosis mutations
    • Pedemonte, N.; Tomati, V.; Sondo, E.; Caci, E.; Millo, E.; Armirotti, A.; Damonte, G.; Zegarra-Moran, O.; Galietta, L. J. Dual activity of aminoarylthiazoles on the trafficking and gating defects of the cystic fibrosis transmembrane conductance regulator chloride channel caused by cystic fibrosis mutations J. Biol. Chem. 2011, 286, 15215-15226
    • (2011) J. Biol. Chem. , vol.286 , pp. 15215-15226
    • Pedemonte, N.1    Tomati, V.2    Sondo, E.3    Caci, E.4    Millo, E.5    Armirotti, A.6    Damonte, G.7    Zegarra-Moran, O.8    Galietta, L.J.9
  • 25
    • 33847122608 scopus 로고    scopus 로고
    • Modulating the folding of P-glycoprotein and cystic fibrosis transmembrane conductance regulator truncation mutants with pharmacological chaperones
    • DOI 10.1124/mol.106.029926
    • Wang, Y.; Loo, T. W.; Bartlett, M. C.; Clarke, D. M. Modulating the folding of P-glycoprotein and cystic fibrosis transmembrane conductance regulator truncation mutants with pharmacological chaperones Mol. Pharmacol. 2007, 71, 751-758 (Pubitemid 46294086)
    • (2007) Molecular Pharmacology , vol.71 , Issue.3 , pp. 751-758
    • Wang, Y.1    Loo, T.W.2    Bartlett, M.C.3    Clarke, D.M.4
  • 26
    • 34347242438 scopus 로고    scopus 로고
    • Structure-activity relationship of 1,4-dihydropyridines as potentiators of the cystic fibrosis transmembrane conductance regulator chloride channel
    • DOI 10.1124/mol.107.034702
    • Pedemonte, N.; Boido, D.; Moran, O.; Giampieri, M.; Mazzei, M.; Ravazzolo, R.; Galietta, L. J. Structure-activity relationship of 1,4-dihydropyridines as potentiators of the cystic fibrosis transmembrane conductance regulator chloride channel Mol. Pharmacol. 2007, 72, 197-207 (Pubitemid 46998539)
    • (2007) Molecular Pharmacology , vol.72 , Issue.1 , pp. 197-207
    • Pedemonte, N.1    Boido, D.2    Moran, O.3    Giampieri, M.4    Mazzei, M.5    Ravazzolo, R.6    Galietta, L.J.V.7
  • 32
    • 72049120101 scopus 로고    scopus 로고
    • Design and synthesis of a hybrid potentiator-corrector agonist of the cystic fibrosis mutant protein DeltaF508-CFTR
    • Mills, A. D.; Yoo, C.; Butler, J. D.; Yang, B.; Verkman, A. S.; Kurth, M. J. Design and synthesis of a hybrid potentiator-corrector agonist of the cystic fibrosis mutant protein DeltaF508-CFTR Bioorg. Med. Chem. Lett. 2010, 20, 87-91
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 87-91
    • Mills, A.D.1    Yoo, C.2    Butler, J.D.3    Yang, B.4    Verkman, A.S.5    Kurth, M.J.6
  • 33
    • 70349096824 scopus 로고    scopus 로고
    • Emerging treatments in cystic fibrosis
    • Jones, A. M.; Helm, J. M. Emerging treatments in cystic fibrosis Drugs 2009, 69, 1903-1910
    • (2009) Drugs , vol.69 , pp. 1903-1910
    • Jones, A.M.1    Helm, J.M.2
  • 34
    • 80053179441 scopus 로고    scopus 로고
    • Cyanoquinolines with independent corrector and potentiator activities restore Δf508-CFTR chloride channel function in cystic fibrosis
    • Phuan, P.-W.; Yang, B.; Knapp, J. M.; Wood, A. B.; Lukacs, G. L.; Kurth, M. J.; Verkman, A. S. Cyanoquinolines with independent corrector and potentiator activities restore ΔF508-CFTR chloride channel function in cystic fibrosis Mol. Pharmacol. 2011, 80, 683-693
    • (2011) Mol. Pharmacol. , vol.80 , pp. 683-693
    • Phuan, P.-W.1    Yang, B.2    Knapp, J.M.3    Wood, A.B.4    Lukacs, G.L.5    Kurth, M.J.6    Verkman, A.S.7
  • 35
    • 79955004745 scopus 로고    scopus 로고
    • Quinoline as a privileged scaffold in cancer drug discovery
    • Solomon, V. R.; Lee, H. Quinoline as a privileged scaffold in cancer drug discovery Curr. Med. Chem. 2011, 18, 1488-508
    • (2011) Curr. Med. Chem. , vol.18 , pp. 1488-508
    • Solomon, V.R.1    Lee, H.2
  • 36
    • 0014785802 scopus 로고
    • 8-Hydroxyquinoline derivatives. Synthesis and biological evaluation of arylglyoxal N -7-amino-5-substituted 8-hydroxyquinoline hemiacetals and 5-phenylglyoxylidenamino-8-hydroxyquinolines
    • Massarani, E.; Nardi, D.; Pozzi, R.; Degen, L.; Magistretti, M. J. 8-Hydroxyquinoline derivatives. Synthesis and biological evaluation of arylglyoxal N -7-amino-5-substituted 8-hydroxyquinoline hemiacetals and 5-phenylglyoxylidenamino-8-hydroxyquinolines J. Med. Chem. 1970, 13, 380-383
    • (1970) J. Med. Chem. , vol.13 , pp. 380-383
    • Massarani, E.1    Nardi, D.2    Pozzi, R.3    Degen, L.4    Magistretti, M.J.5
  • 37
    • 78650241371 scopus 로고    scopus 로고
    • Second-generation substituted quinolines as anticancer drugs for breast cancer
    • Heiniger, B.; Gakhar, G.; Prasain, K.; Hua, D. H.; Nguyen, T. A. Second-generation substituted quinolines as anticancer drugs for breast cancer Anticancer Res. 2010, 30, 3927-3932
    • (2010) Anticancer Res. , vol.30 , pp. 3927-3932
    • Heiniger, B.1    Gakhar, G.2    Prasain, K.3    Hua, D.H.4    Nguyen, T.A.5
  • 38
    • 1542707126 scopus 로고
    • Action of phosphorus oxychloride upon methyl- and ethylacetanilide. Synthesis of γ-chloroisoquinocyanines
    • Fischer, O.; Muller, A.; Vilsmeier, A. Action of phosphorus oxychloride upon methyl- and ethylacetanilide. Synthesis of γ-chloroisoquinocyanines J. Prakt. Chem. 1925, 109, 69-87
    • (1925) J. Prakt. Chem. , vol.109 , pp. 69-87
    • Fischer, O.1    Muller, A.2    Vilsmeier, A.3
  • 39
    • 84975874144 scopus 로고
    • Action of phosphorus halides on alkylformanilides. A new method for the preparation of secondary and tertiary p -alkylaminonobenzaldehydes
    • Vilsmeier, A.; Haack, A. Action of phosphorus halides on alkylformanilides. A new method for the preparation of secondary and tertiary p -alkylaminonobenzaldehydes Ber. 1927, 60B, 119-122
    • (1927) Ber. , vol.60 , pp. 119-122
    • Vilsmeier, A.1    Haack, A.2
  • 40
    • 25444475650 scopus 로고    scopus 로고
    • Synthesis and characterization of some new aryl quinolyl α,β-unsaturated ketones
    • Moussaoui, F.; Belfaitah, A.; Debache, A.; Rhouati, S. Synthesis and characterization of some new aryl quinolyl α,β-unsaturated ketones J. Soc. Alger. Chim. 2002, 12, 71-78
    • (2002) J. Soc. Alger. Chim. , vol.12 , pp. 71-78
    • Moussaoui, F.1    Belfaitah, A.2    Debache, A.3    Rhouati, S.4
  • 41
    • 84856936023 scopus 로고    scopus 로고
    • Wavefunction, Inc. Irvine, CA.
    • Spartan '10; Wavefunction, Inc.: Irvine, CA.
    • Spartan '10
  • 42
    • 0037571112 scopus 로고    scopus 로고
    • Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94
    • Halgren, T. A. Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94 J. Comput. Chem. 1996, 17, 490-519 (Pubitemid 126567067)
    • (1996) Journal of Computational Chemistry , vol.17 , Issue.5-6 , pp. 490-519
    • Halgren, T.A.1
  • 43
    • 43049141516 scopus 로고    scopus 로고
    • The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: Two new functionals and systematic testing of four M06-class functionals and 12 other functionals
    • Zhao, Y.; Truhlar, D. G. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals Theor. Chem. Acc. 2008, 120, 215-241
    • (2008) Theor. Chem. Acc. , vol.120 , pp. 215-241
    • Zhao, Y.1    Truhlar, D.G.2
  • 45
    • 66349120487 scopus 로고    scopus 로고
    • Universal solvation model based on solute electron density and a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions
    • Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. Universal solvation model based on solute electron density and a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions J. Phys. Chem. B 2009, 113, 6378-6396
    • (2009) J. Phys. Chem. B , vol.113 , pp. 6378-6396
    • Marenich, A.V.1    Cramer, C.J.2    Truhlar, D.G.3
  • 46
    • 0031207660 scopus 로고    scopus 로고
    • Intramolecular hydrogen bonding, Gauche interactions, and thermodynamic functions of 1,2-ethanediamine, 1,2-ethanediol, and 2-aminoethanol: A global conformational analysis
    • Chang, Y.-P.; Su, T.-M.; Li, T.-W.; Chao, I. Intramolecular hydrogen bonding, gauche interactions, and thermodynamic functions of 1,2-ethanediamine, 1,2-ethanediol, and 2-aminoethanol: a global conformational analysis J. Phys. Chem. A 1997, 101, 6107-6117 (Pubitemid 127585031)
    • (1997) Journal of Physical Chemistry A , vol.101 , Issue.34 , pp. 6107-6117
    • Chang, Y.-P.1    Su, T.-M.2    Li, T.-W.3    Chao, I.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.