메뉴 건너뛰기




Volumn 56, Issue 11, 2013, Pages 4509-4520

Synthesis, 18F-radiolabeling, and in vivo biodistribution studies of N-fluorohydroxybutyl isatin sulfonamides using positron emission tomography

Author keywords

[No Author keywords available]

Indexed keywords

CASPASE 3 INHIBITOR; CASPASE 7; FLUORIDE; FLUORINE 18; ISATIN DERIVATIVE; N [(3 (F 18 ) FLUORO 4 HYDROXYBUTYL) 5 (1 2 (METHOXYMETHYL)PYRROLIDINYL)SULFONYL] ISATIN; N [4 (F 18) FLUORO 3 HYDROXYBUTYL] ISATIN; SULFONAMIDE; UNCLASSIFIED DRUG; CASPASE 3; CASPASE INHIBITOR; DRUG DERIVATIVE; FLUORINE; ISATIN; N (3 FLUORO 4 HYDROXYBUTYL) 5 (1 (2 (METHOXYMETHYL)PYRROLIDINYL)SULFONYL)ISATIN; N (4 FLUORO 3 HYDROXYBUTYL) 5 (1 (2 (METHOXYMETHYL)PYRROLIDINYL)SULFONYL)ISATIN; N-(3-FLUORO-4-HYDROXYBUTYL)-5-(1-(2-(METHOXYMETHYL)PYRROLIDINYL)SULFONYL)ISATIN; N-(4-FLUORO-3-HYDROXYBUTYL)-5-(1-(2-(METHOXYMETHYL)PYRROLIDINYL)SULFONYL)ISATIN; RADIOPHARMACEUTICAL AGENT;

EID: 84879044088     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400257a     Document Type: Article
Times cited : (12)

References (38)
  • 1
    • 0034641918 scopus 로고    scopus 로고
    • The biochemistry of apoptosis
    • Hengartner, M. O. The biochemistry of apoptosis Nature 2000, 407, 770-776
    • (2000) Nature , vol.407 , pp. 770-776
    • Hengartner, M.O.1
  • 2
    • 0029956641 scopus 로고    scopus 로고
    • Decreased apoptosis in the brain and premature lethality in CPP32- deficient mice
    • DOI 10.1038/384368a0
    • Kuida, K.; Zheng, T. S.; Na, S. Q.; Kuan, C. Y.; Yang, D.; Karasuyama, H.; Rakic, P.; Flavell, R. A. Decreased apoptosis in the brain and premature lethality in CPP32-deficient mice Nature 1996, 384, 368-372 (Pubitemid 26408520)
    • (1996) Nature , vol.384 , Issue.6607 , pp. 368-372
    • Kulda, K.1    Zheng, T.S.2    Na, S.3    Kuan, C.-Y.4    Yang, D.5    Karasuyama, H.6    Rakic, P.7    Flavell, R.A.8
  • 4
    • 0032493910 scopus 로고    scopus 로고
    • Reduced apoptosis and cytochrome C-mediated caspase activation in mice lacking Caspase 9
    • DOI 10.1016/S0092-8674(00)81476-2
    • Kuida, K.; Haydar, T. F.; Kuan, C. Y.; Gu, Y.; Taya, C.; Karasuyama, H.; Su, M. S. S.; Rakic, P.; Flavell, R. A. Reduced apoptosis and cytochrome c-mediated caspase activation in mice lacking caspase 9 Cell 1998, 94, 325-337 (Pubitemid 28376077)
    • (1998) Cell , vol.94 , Issue.3 , pp. 325-337
    • Kuida, K.1    Haydar, T.F.2    Kuan, C.-Y.3    Gu, Y.4    Taya, C.5    Karasuyama, H.6    Su, M.S.-S.7    Rakic, P.8    Flavell, R.A.9
  • 7
    • 0036644078 scopus 로고    scopus 로고
    • Death to flies: Drosophila as a model system to study programmed cell death
    • Richardson, H.; Kumar, S. Death to flies: Drosophila as a model system to study programmed cell death J. Immunol. Methods 2002, 265, 21-38
    • (2002) J. Immunol. Methods , vol.265 , pp. 21-38
    • Richardson, H.1    Kumar, S.2
  • 8
    • 0032885388 scopus 로고    scopus 로고
    • Mammalian caspases: Structure, activation, substrates, and functions during apoptosis
    • DOI 10.1146/annurev.biochem.68.1.383
    • Earnshaw, W. C.; Martins, L. M.; Kaufmann, S. H. Mammalian caspases: Structure, activation, substrates, and functions during apoptosis Annu. Rev. Biochem. 1999, 68, 383-424 (Pubitemid 29449198)
    • (1999) Annual Review of Biochemistry , vol.68 , pp. 383-424
    • Earnshaw, W.C.1    Martins, L.M.2    Kaufmann, S.H.3
  • 9
    • 0036931366 scopus 로고    scopus 로고
    • Caspases: Keys in the ignition of cell death
    • Denault, J. B.; Salvesen, G. S. Caspases: Keys in the ignition of cell death Chem. Rev. 2002, 102, 4489-4499
    • (2002) Chem. Rev. , vol.102 , pp. 4489-4499
    • Denault, J.B.1    Salvesen, G.S.2
  • 10
    • 0032575750 scopus 로고    scopus 로고
    • Caspases: Enemies within
    • Thornberry, N. A.; Lazebnik, Y. Caspases: Enemies within Science 1998, 281, 1312-1316 (Pubitemid 28406817)
    • (1998) Science , vol.281 , Issue.5381 , pp. 1312-1316
    • Thornberry, N.A.1    Lazebnik, Y.2
  • 11
    • 0030814675 scopus 로고    scopus 로고
    • Caspases: Killer proteases
    • DOI 10.1016/S0968-0004(97)01085-2, PII S0968000497010852
    • Nicholson, D. W.; Thornberry, N. A. Caspases: Killer proteases Trends Biochem. Sci. 1997, 22, 299-306 (Pubitemid 27327087)
    • (1997) Trends in Biochemical Sciences , vol.22 , Issue.8 , pp. 299-306
    • Nicholson, D.W.1    Thornberry, N.A.2
  • 14
    • 84877826940 scopus 로고    scopus 로고
    • Influence of 4- or 5-substituents on the pyrrolidine ring of 5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin derivatives on their inhibitory activities towards caspases-3 and -7
    • Limpachayaporn, P.; Riemann, B.; Kopka, K.; Schober, O.; Schäfers, M.; Haufe, G. Influence of 4- or 5-substituents on the pyrrolidine ring of 5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin derivatives on their inhibitory activities towards caspases-3 and -7 Eur. J. Med. Chem. 2013, 64, 562-578
    • (2013) Eur. J. Med. Chem. , vol.64 , pp. 562-578
    • Limpachayaporn, P.1    Riemann, B.2    Kopka, K.3    Schober, O.4    Schäfers, M.5    Haufe, G.6
  • 15
    • 84882927518 scopus 로고    scopus 로고
    • Fluorine-18 chemistry for molecular imaging with positron emission tomography: Molecular imaging, biomedical materials and pharmaceuticals
    • In, 1 st ed. Tressaud, A. Haufe, G. Elsevier Science: Amsterdam
    • Dollé, F.; Roeda, D.; Kuhnast, B.; Lasne, M.-C. Fluorine-18 chemistry for molecular imaging with positron emission tomography: Molecular imaging, biomedical materials and pharmaceuticals. In Fluorine and Health, 1 st ed.; Tressaud, A.; Haufe, G., Eds.; Elsevier Science: Amsterdam, 2008; pp 3-65.
    • (2008) Fluorine and Health , pp. 3-65
    • Dollé, F.1    Roeda, D.2    Kuhnast, B.3    Lasne, M.-C.4
  • 17
    • 28144443339 scopus 로고    scopus 로고
    • N-benzylisatin sulfonamide analogues as potent caspase-3 inhibitors: Synthesis, in vitro activity, and molecular modeling studies
    • DOI 10.1021/jm0506625
    • Chu, W. H.; Zhang, J.; Zeng, C. B.; Rothfuss, J.; Tu, Z. D.; Chu, Y. X.; Reichert, D. E.; Welch, M. J.; Mach, R. H. N -Benzylisatin sulfonamide analogues as potent caspase-3 inhibitors: Synthesis, in vitro activity, and molecular modeling studies J. Med. Chem. 2005, 48, 7637-7647 (Pubitemid 41698804)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.24 , pp. 7637-7647
    • Chu, W.1    Zhang, J.2    Zeng, C.3    Rothfuss, J.4    Tu, Z.5    Chu, Y.6    Reichert, D.E.7    Welch, M.J.8    Mach, R.H.9
  • 18
    • 79953281429 scopus 로고    scopus 로고
    • Synthesis and evaluation of isatin analogs as caspase-3 inhibitors: Introduction of a hydrophilic group increases potency in a whole cell assay
    • Chu, W.; Rothfuss, J.; Zhou, D.; Mach, R. H. Synthesis and evaluation of isatin analogs as caspase-3 inhibitors: Introduction of a hydrophilic group increases potency in a whole cell assay Bioorg. Med. Chem. Lett. 2011, 21, 2192-2197
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 2192-2197
    • Chu, W.1    Rothfuss, J.2    Zhou, D.3    Mach, R.H.4
  • 20
    • 66749129069 scopus 로고    scopus 로고
    • Fluorinated isatin derivatives. Part 2. New N-substituted 5-pyrrolidinylsulfonyl isatins as potential tools for molecular imaging of caspases in apoptosis
    • Podichetty, A. K.; Wagner, S.; Schröer, S.; Faust, A.; Schäfers, M.; Schober, O.; Kopka, K.; Haufe, G. Fluorinated isatin derivatives. Part 2. New N-substituted 5-pyrrolidinylsulfonyl isatins as potential tools for molecular imaging of caspases in apoptosis J. Med. Chem. 2009, 52, 3484-95
    • (2009) J. Med. Chem. , vol.52 , pp. 3484-3495
    • Podichetty, A.K.1    Wagner, S.2    Schröer, S.3    Faust, A.4    Schäfers, M.5    Schober, O.6    Kopka, K.7    Haufe, G.8
  • 22
    • 62949137154 scopus 로고    scopus 로고
    • Fluorinated isatin derivatives. Part 1: Synthesis of new N-substituted (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatins as potent caspase-3 and -7 inhibitors
    • Podichetty, A. K.; Faust, A.; Kopka, K.; Wagner, S.; Schober, O.; Schäfers, M.; Haufe, G. Fluorinated isatin derivatives. Part 1: Synthesis of new N-substituted (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatins as potent caspase-3 and -7 inhibitors Bioorg. Med. Chem. 2009, 17, 2680-2688
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 2680-2688
    • Podichetty, A.K.1    Faust, A.2    Kopka, K.3    Wagner, S.4    Schober, O.5    Schäfers, M.6    Haufe, G.7
  • 23
    • 77953402965 scopus 로고    scopus 로고
    • Fluorinated isatin derivatives. Part 3. New side-chain fluoro-functionalized pyrrolidinyl sulfonyl isatins as potent caspase-3 and-7 inhibitors
    • Podichetty, A. K.; Wagner, S.; Faust, A.; Schäfers, M.; Schober, O.; Kopka, K.; Haufe, G. Fluorinated isatin derivatives. Part 3. New side-chain fluoro-functionalized pyrrolidinyl sulfonyl isatins as potent caspase-3 and-7 inhibitors Future Med. Chem. 2009, 1, 969-989
    • (2009) Future Med. Chem. , vol.1 , pp. 969-989
    • Podichetty, A.K.1    Wagner, S.2    Faust, A.3    Schäfers, M.4    Schober, O.5    Kopka, K.6    Haufe, G.7
  • 24
    • 84875215747 scopus 로고    scopus 로고
    • Synthesis of new fluorinated, 2-substituted 5-pyrrolidinylsulfonyl isatin derivatives as caspase-3 and caspase-7 inhibitors: Nonradioactive counterparts of putative PET-compatible apoptosis imaging agents
    • Limpachayaporn, P.; Schäfers, M.; Schober, O.; Kopka, K.; Haufe, G. Synthesis of new fluorinated, 2-substituted 5-pyrrolidinylsulfonyl isatin derivatives as caspase-3 and caspase-7 inhibitors: Nonradioactive counterparts of putative PET-compatible apoptosis imaging agents Bioorg. Med. Chem. 2013, 21, 2025-2036
    • (2013) Bioorg. Med. Chem. , vol.21 , pp. 2025-2036
    • Limpachayaporn, P.1    Schäfers, M.2    Schober, O.3    Kopka, K.4    Haufe, G.5
  • 29
    • 79959965397 scopus 로고    scopus 로고
    • Metabolite identification of a radiotracer by electrochemistry coupled to liquid chromatography with mass spectrometric and radioactivity detection
    • Baumann, A.; Faust, A.; Law, M. P.; Kuhlmann, M. T.; Kopka, K.; Schäfers, M.; Karst, U. Metabolite identification of a radiotracer by electrochemistry coupled to liquid chromatography with mass spectrometric and radioactivity detection Anal. Chem. 2011, 83, 5415-5421
    • (2011) Anal. Chem. , vol.83 , pp. 5415-5421
    • Baumann, A.1    Faust, A.2    Law, M.P.3    Kuhlmann, M.T.4    Kopka, K.5    Schäfers, M.6    Karst, U.7
  • 33
    • 0030272778 scopus 로고    scopus 로고
    • The use of 3-methoxymethyl-16β,17β-epiestriol-O-cyclic sulfone as the precursor in the synthesis of F-18 16α-fluoroestradiol
    • DOI 10.1016/S0969-8051(96)00126-6, PII S0969805196001266
    • 18F-16α-fluoroestradiol Nucl. Med. Biol. 1996, 23, 911-915 (Pubitemid 26392233)
    • (1996) Nuclear Medicine and Biology , vol.23 , Issue.7 , pp. 911-915
    • Lim, J.L.1    Zheng, L.2    Berridge, M.S.3    Tewson, T.J.4
  • 34
    • 0029055872 scopus 로고
    • Synthesis and conformational analysis of 2,9-disubstituted 1-oxaquinolizidines
    • Börjesson, L.; Csoregh, I.; Welch, C. J. Synthesis and conformational analysis of 2,9-disubstituted 1-oxaquinolizidines J. Org. Chem. 1995, 60, 2989-2999
    • (1995) J. Org. Chem. , vol.60 , pp. 2989-2999
    • Börjesson, L.1    Csoregh, I.2    Welch, C.J.3
  • 35
    • 76249133932 scopus 로고    scopus 로고
    • (-)-Complanine, an inflammatory substance of marine fireworm: A synthetic study
    • No. 12.
    • Nakamura, K.; Tachikawa, Y.; Uemura, D. (-)-Complanine, an inflammatory substance of marine fireworm: a synthetic study. Beilstein J. Org. Chem. 2009, 5, No. 12.
    • (2009) Beilstein J. Org. Chem. , vol.5
    • Nakamura, K.1    Tachikawa, Y.2    Uemura, D.3
  • 36
    • 33845470265 scopus 로고
    • Anhydrous" tetrabutylammonium fluoride: A mild but highly efficient source of nucleophilic fluoride ion
    • Cox, D. P.; Terpinski, J.; Lawrynowicz, W. "Anhydrous" tetrabutylammonium fluoride: A mild but highly efficient source of nucleophilic fluoride ion J. Org. Chem. 1984, 49, 3216-3219
    • (1984) J. Org. Chem. , vol.49 , pp. 3216-3219
    • Cox, D.P.1    Terpinski, J.2    Lawrynowicz, W.3
  • 37
    • 33845550463 scopus 로고
    • Instability of anhydrous tetra- n -alkylammonium fluorides
    • Sharma, R. K.; Fry, J. L. Instability of anhydrous tetra- n -alkylammonium fluorides J. Org. Chem. 1983, 48 (12) 2112-2114
    • (1983) J. Org. Chem. , vol.48 , Issue.12 , pp. 2112-2114
    • Sharma, R.K.1    Fry, J.L.2
  • 38
    • 38849134893 scopus 로고    scopus 로고
    • Facile nucleophilic fluorination reactions using tert -alcohols as a reaction medium: Significantly enhanced reactivity of alkali metal fluorides and improved selectivity
    • Kim, D. W.; Jeong, H. J.; Litn, S. T.; Sohn, M. H.; Katzenellenbogen, J. A.; Chi, D. Y. Facile nucleophilic fluorination reactions using tert -alcohols as a reaction medium: Significantly enhanced reactivity of alkali metal fluorides and improved selectivity J. Org. Chem. 2008, 73, 957-962
    • (2008) J. Org. Chem. , vol.73 , pp. 957
    • Kim, D.W.1    Jeong, H.J.2    Litn, S.T.3    Sohn, M.H.4    Katzenellenbogen, J.A.5    Chi, D.Y.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.