Design and synthesis of a novel anthracene-based fluorescent probe through the application of the Suzuki–Miyaura cross-coupling reaction

JM Beechem L Brand (1985) ArticleTitleTime-resolved fluorescence of proteins Annu Rev Biochem 54 43–71 Occurrence Handle3896124 Occurrence Handle10.1146/annurev.bi.54.070185.000355 Occurrence Handle1:STN:280:DyaL2M3nsl2qtw%3D%3D M-P Brun L Bischoff C Garbay (2004) ArticleTitleA very short route to enantiomerically pure coumarin-bearing fluorescent amino acids Angew Chem Int Ed 43 3432–3436 Occurrence Handle10.1002/anie.200454116 Occurrence Handle1:CAS:528:DC%2BD2cXlvVSns7k%3D TR Cech BL Bass (1986) ArticleTitleBiological catalysis by RNA Annu Rev Biochem 55 599–629 Occurrence Handle2427016 Occurrence Handle10.1146/annurev.bi.55.070186.003123 Occurrence Handle1:CAS:528:DyaL28XlsVymsbs%3D TR Cech D Herschlag JA Piccirilli AM Pyle (1992) ArticleTitleRNA catalysis by a group I ribozyme. Developing a model for transition state stabilization J Biol Chem 267 17479–17482 Occurrence Handle1381347 Occurrence Handle1:CAS:528:DyaK38XltVKrtro%3D H Du RA Fuh J Li A Corkan JS Lindsey (1998) ArticleTitlePhotochem CAD: a computer-aided design and research tool in photochemistry Photochem Photobiol 68 141–142 Occurrence Handle1:CAS:528:DyaK1cXlsFCqsL8%3D MR Eftink CA Ghiron (1977) ArticleTitleExposure of tryptophanyl residues and protein dynamics Biochemistry 16 5546–5551 Occurrence Handle921949 Occurrence Handle10.1021/bi00644a024 Occurrence Handle1:CAS:528:DyaE1cXhvFGg GA Elove AF Chaffotte H Roder ME Goldberg (1992) ArticleTitleEarly steps in cytochrome c folding probed by time-resolved circular dichroism and fluorescence spectroscopy Biochemistry 31 6876–6883 Occurrence Handle1322172 Occurrence Handle10.1021/bi00145a003 Occurrence Handle1:CAS:528:DyaK38Xks1GjtLc%3D C Guerrier-Takada K Gardiner T Marsh N Pace S Altman (1983) ArticleTitleThe RNA moiety of ribonuclease P is the catalytic subunit of the enzyme Cell 35 849–857 Occurrence Handle6197186 Occurrence Handle10.1016/0092-8674(83)90117-4 Occurrence Handle1:CAS:528:DyaL2cXpvFShsA%3D%3D K Guzow M Szabelski J Malicka W Wiczk (2001) ArticleTitleSynthesis of a new, highly fluorescent amino acid derivative: N-[(tert-butoxy)carbonyl]-3-[2-(1H-indol-3-yl)benzoxazol-5-yl]-L-alanine methyl ester Helv Chim Acta 84 1086–1092 Occurrence Handle10.1002/1522-2675(20010516)84:5<1086::AID-HLCA1086>3.0.CO;2-D Occurrence Handle1:CAS:528:DC%2BD3MXktFyitLw%3D K Hamada N Kameshima A Szymańska A Wegner L Łankiewicz H Shinohara M Takia M Sisido (2005) ArticleTitlePosition-specific incorporation of a highly photodurable and blue-laser excitable fluorescent amino acid into proteins for fluorescence sensing Bioorg Med Chem 13 3379–3384 Occurrence Handle15848750 Occurrence Handle10.1016/j.bmc.2005.03.014 Occurrence Handle1:CAS:528:DC%2BD2MXjsFCitLk%3D RR Hudgins F Huang G Gramlich WM Nau (2002) ArticleTitleA fluorescence-based method for direct measurement of submicrosecond intramolecular contact formation in biopolymers: an exploratory study with polypeptides J Am Chem Soc 124 556–564 Occurrence Handle11804484 Occurrence Handle10.1021/ja010493n Occurrence Handle1:CAS:528:DC%2BD38XhsVWqsw%3D%3D G Kóczán G Csík A Csámpai E Balog S Bősze P Sohár F Hudecz (2001) ArticleTitleSynthesis and characterization of 4-ethoxymethylene-2-[1]-naphthyl-5(4H)-oxazolone and its fluorescent amino acid derivatives Tetrahedron 57 4589–4598 Occurrence Handle10.1016/S0040-4020(01)00332-5 Kotha S, Ghosh AK, Deodhar KD (2004) Synthesis of symmetrical and unsymmetrical 9,10-diarylanthracene derivatives via bis-Suzuki–Miyaura cross-coupling reaction. Synthesis 549–557 S Kotha K Lahiri D Kashinath (2002) ArticleTitleRecent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis Tetrahedron 58 9633–9695 Occurrence Handle10.1016/S0040-4020(02)01188-2 Occurrence Handle1:CAS:528:DC%2BD38XovVSmtbg%3D S Kotha VR Shah S Halder V Ramnathan K Lahiri (2007) ArticleTitleSynthesis of bis-armed amino acid derivatives via the alkylation of ethyl isocyanoacetate and the Suzuki–Miyaura cross-coupling reaction Amino Acids 32 387–394 Occurrence Handle17031480 Occurrence Handle10.1007/s00726-006-0402-2 Occurrence Handle1:CAS:528:DC%2BD2sXjvFams7w%3D T Kouyama K Mihashi (1981) ArticleTitleFluorimetry study of N-(1-pyrenyl)iodoacetamide-labelled F-actin. Local structural change of actin protomer both on polymerization and on binding of heavy meromyosin Eur J Biochem 114 33–38 Occurrence Handle7011802 Occurrence Handle1:CAS:528:DyaL3MXhtFKhu7w%3D Occurrence Handle10.1111/j.1432-1033.1981.tb06167.x JR Lakowicz (1983) Principles of fluorescence spectroscopy Plenum Press New York JR Lakowicz G Weber (1973) ArticleTitleQuenching of protein fluorescence by oxygen. Detection of structural fluctuations in proteins on the nanosecond time scale Biochemistry 12 4171–4179 Occurrence Handle4200894 Occurrence Handle10.1021/bi00745a021 Occurrence Handle1:CAS:528:DyaE3sXlsVelt7o%3D Malakhov AD, Skorobogatyi MV, Prokhorenko IA, Gontarev SV, Kozhich DT, Stetsenko DA, Stepanova IA, Shenkarev ZO, Berlin YA, Korshun VA (2004) 1-(Phenylethynyl)pyrene and 9,10-bis(phenylethynyl)anthracene, useful fluorescent dyes for DNA labeling: excimer formation and energy transfer. Eur J Org Chem 1298–1307 N Miyaura A Suzuki (1995) ArticleTitlePalladium-catalyzed cross-coupling reactions of organoboron compounds Chem Rev 95 2457–2483 Occurrence Handle10.1021/cr00039a007 Occurrence Handle1:CAS:528:DyaK2MXoslGiurg%3D JW Petrich NC Change DB McDonald GR Fleming (1983) ArticleTitleOn the origin of nonexponential fluorescence decay in tryptophan and its derivatives J Am Chem Soc 105 3824–3832 Occurrence Handle10.1021/ja00350a014 Occurrence Handle1:CAS:528:DyaL3sXit1Cmu7Y%3D JW Petrich JW Longworth GR Fleming (1987) ArticleTitleInternal motion and electron transfer in proteins: a picosecond fluorescence study of three homologous azurins Biochemistry 26 2711–2722 Occurrence Handle3111523 Occurrence Handle10.1021/bi00384a010 Occurrence Handle1:CAS:528:DyaL2sXhvFWnsL4%3D A Rzeska J Malicka K Guzow M Szabelski W Wiczk (2001) ArticleTitleNew highly fluorescent amino-acid derivatives: substituted 3-[2-(phenyl)benzoxazol-5-yl]-alanines: synthesis and photophysical properties J Photochem Photobiol A 146 9–18 Occurrence Handle10.1016/S1010-6030(01)00591-3 Occurrence Handle1:CAS:528:DC%2BD3MXosF2nu7c%3D DE Stack AL Hill CB Diffendaffer NM Burns (2002) ArticleTitleSynthesis of a new fluorescent probe specific for catechols Org Lett 4 4487–4490 Occurrence Handle12465919 Occurrence Handle10.1021/ol027000j Occurrence Handle1:CAS:528:DC%2BD38XovFSkur0%3D KG Steinhauser P Woolley B Epe J Dijk (1982) ArticleTitleStructure of ribosomal protein L6 from Escherichia coli. A fluorescence study Eur J Biochem 127 587–595 Occurrence Handle6756916 Occurrence Handle1:STN:280:DyaL3s%2FnvFaktQ%3D%3D Occurrence Handle10.1111/j.1432-1033.1982.tb06913.x N Sugimoto M Tomka R Kierzek PC Bevilaqua DH Turner (1989) ArticleTitleEffects of substrate structure on the kinetics of circle opening reactions of the self-splicing intervening sequence from Tetrahymena thermophila: evidence for substrate and Mg2+ binding interactions Nucleic Acids Res 17 355–371 Occurrence Handle2643083 Occurrence Handle10.1093/nar/17.1.355 Occurrence Handle1:CAS:528:DyaL1MXitVynsr8%3D KMK Swamy YJ Jang MS Park HS Koh SK Lee YJ Yoona J Yoona (2005) ArticleTitleA sorbitol-selective fluorescence sensor Tetrahedon Lett 46 3453–3456 Occurrence Handle10.1016/j.tetlet.2005.03.121 Occurrence Handle1:CAS:528:DC%2BD2MXjs1SktL0%3D ME Vázquez DE Rothman B Imperiali (2004) ArticleTitleA new environment-sensitive fluorescent amino acid for Fmoc-based solid phase peptide synthesis Org Biomol Chem 2 1965–1966 Occurrence Handle10.1039/b408001g Occurrence Handle1:CAS:528:DC%2BD2cXls1ertb8%3D