“Reduced” Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy
Large Stokes-shift coumarin dyes with an O-phosphorylated 4-(hydroxymethyl)-2,2-dimethyl-1,2,3,4-tetrahydroquinoline fragment emitting in the blue, green, and red regions of the visible spectrum were synthesized. For this purpose, N-substituted and O-protected 1,2-dihydro-7-hydroxy-2,2,4-trimethylqu...
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Wiley-VCH Verlag
2016
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| LEADER | 12567caa a22015977a 4500 | ||
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| 001 | PAPER-16468 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518204729.0 | ||
| 008 | 190411s2016 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-84978288262 | |
| 024 | 7 | |2 cas |a Coumarins; Fluorescent Dyes; Quinolines | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a CEUJE | ||
| 100 | 1 | |a Nizamov, S. | |
| 245 | 1 | 0 | |a “Reduced” Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy |
| 260 | |b Wiley-VCH Verlag |c 2016 | ||
| 270 | 1 | 0 | |m Belov, V.N.; Department of NanoBiophotonics, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, Germany; email: vbelov@gwdg.de |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Fernández-Suárez, M., Ting, A.Y., (2008) Nat. Rev. Mol. Cell Biol., 9, pp. 929-943 | ||
| 504 | |a Gonçalves, M.S.T., (2009) Chem. Rev., 109, pp. 190-212 | ||
| 504 | |a Lavis, L.D., Raines, R.T., (2014) ACS Chem. Biol., 9, pp. 855-866 | ||
| 504 | |a Umezawa, K., Citterio, D., Suzuki, K., (2014) Anal. Sci., 30, pp. 327-349 | ||
| 504 | |a van de Linde, S., Sauer, M., (2014) Chem. Soc. Rev., 43, pp. 1076-1087 | ||
| 504 | |a Chozinski, T.J., Gagnon, L.A., Vaughan, J.C., (2014) FEBS Lett., 588, pp. 3603-3612 | ||
| 504 | |a Godin, A.G., Lounis, B., Cognet, L., (2014) Biophys. J., 107, pp. 1777-1784 | ||
| 504 | |a Grimm, J.B., English, B.P., Chen, J., Slaughter, J.P., Zhang, Z., Revyakin, A., Patel, R., Lavis, L.D., (2015) Nat. Methods, 12, pp. 244-250 | ||
| 504 | |a Do, M., Isaacson, S.A., McDermott, G., Le Gros, M.A., Larabell, C.A., (2015) Arch. Biochem. Biophys., 581, pp. 111-121 | ||
| 504 | |a Carzaniga, R., Domart, M.-C., Collinson, L.M., Duke, E., (2014) Protoplasma, 251, pp. 449-458 | ||
| 504 | |a Rigort, A., Plitzko, J.M., (2015) Arch. Biochem. Biophys., 581, pp. 122-130 | ||
| 504 | |a Lučić, V., Rigort, A., Baumeister, W., (2013) J. Cell Biol., 202, pp. 407-419 | ||
| 504 | |a Möckl, L., Lamb, D.C., Bräuchle, C., (2014) Angew. Chem. Int. Ed., 53, pp. 13972-13977 | ||
| 504 | |a (2014) Angew. Chem., 126, pp. 14 192-14 197 | ||
| 504 | |a Willig, K.I., Barrantes, F.J., (2014) Curr. Opin. Chem. Biol., 20, pp. 16-21 | ||
| 504 | |a Hensel, M., Klingauf, J., Piehler, J., (2013) Biol. Chem., 394, pp. 1097-1113 | ||
| 504 | |a Hell, S.W., Sahl, S.J., Bates, M., Zhuang, X., Heintzmann, R., Booth, M.J., Bewersdorf, J., Cordes, T., (2015) J. Phys. D: Appl. Phys., 48, p. 443001 | ||
| 504 | |a Eggeling, C., Hell, S.W., (2015) Far-Field Optical Nanoscopy, pp. 3-25. , in, (Eds., P. Tinnefeld, C. Eggeling, S. W. Hell, Springer, Berlin | ||
| 504 | |a Gould, T.J., Pellett, P.A., Bewersdorf, J., (2013) Fluorescence Microscopy: From Principles to Biological Applications, pp. 375-392. , in, (Ed., U. Kubitscheck, Wiley-VCH, Weinheim | ||
| 504 | |a Sednev, M.V., Belov, V.N., Hell, S.W., (2015) Methods Appl. Fluoresc., 3, p. 042004 | ||
| 504 | |a Fu, M., Xiao, Y., Qian, X., Zhao, D., Xu, Y., (2008) Chem. Commun., pp. 1780-1782 | ||
| 504 | |a Koide, Y., Urano, Y., Hanaoka, K., Terai, T., Nagano, T., (2011) ACS Chem. Biol., 6, pp. 600-608 | ||
| 504 | |a Koide, Y., Urano, Y., Hanaoka, K., Piao, W., Kusakabe, M., Saito, N., Terai, T., Nagano, T., (2012) J. Am. Chem. Soc., 134, pp. 5029-5031 | ||
| 504 | |a Lukinavicius, G., Umezawa, K., Olivier, N., Honigmann, A., Yang, G., Plass, T., Mueller, V., Johnsson, K., (2013) Nat. Chem., 5, pp. 132-139 | ||
| 504 | |a Lukinavicius, G., Reymond, L., D'Este, E., Masharina, A., Gottfert, F., Ta, H., Guther, A., Johnsson, K., (2014) Nat. Methods, 11, pp. 731-733 | ||
| 504 | |a Kolmakov, K., Hebisch, E., Wolfram, T., Nordwig, L.A., Wurm, C.A., Ta, H., Westphal, V., Hell, S.W., (2015) Chem. Eur. J., 21, pp. 13344-13356 | ||
| 504 | |a Langhals, H., Becherer, T., Lindner, J., Obermeier, A., (2007) Eur. J. Org. Chem., pp. 4328-4336 | ||
| 504 | |a Langhals, H., Zgela, D., Lüling, R., (2015) J. Org. Chem., 80, pp. 12146-12150 | ||
| 504 | |a Niko, Y., Didier, P., Mely, Y., Konishi, G.-I., Klymchenko, A.S., (2016) Sci. Rep., 6, p. 18870 | ||
| 504 | |a Wu, L., Burgess, K., (2008) Org. Lett., 10, pp. 1779-1782 | ||
| 504 | |a Horváth, P., Šebej, P., Šolomek, T., Klán, P., (2015) J. Org. Chem., 80, pp. 1299-1311 | ||
| 504 | |a Smith, J.A., West, R.M., (2004), Eur. Pat., EP1392776A2; Chevalier, A., Renard, P.-Y., Romieu, A., (2014) Chem. Eur. J., 20, pp. 8330-8337 | ||
| 504 | |a Wang, C., Fukazawa, A., Taki, M., Sato, Y., Higashiyama, T., Yamaguchi, S., (2015) Angew. Chem. Int. Ed., 54, pp. 15213-15217 | ||
| 504 | |a (2015) Angew. Chem., 127, pp. 15 428-15 432 | ||
| 504 | |a Nizamov, S., Willig, K.I., Sednev, M.V., Belov, V.N., Hell, S.W., (2012) Chem. Eur. J., 18, pp. 16339-16348 | ||
| 504 | |a Schill, H., Nizamov, S., Bottanelli, F., Bierwagen, J., Belov, V.N., Hell, S.W., (2013) Chem. Eur. J., 19, pp. 16556-16565 | ||
| 504 | |a Eggeling, C., Widengren, J., Rigler, R., in, C.A.M.S., (1999) Applied Fluorescence in Chemistry, Biology and Medicine, pp. 193-240. , (Eds., W. Rettig, B. Strehmel, S. Schrader, H. Seifert, Springer, Berlin Heidelberg | ||
| 504 | |a Kunjappu, J.T., Rao, K.N., (1987) J. Photochem., 39, pp. 135-143 | ||
| 504 | |a Winters, B.H., Mandelberg, H.I., Mohr, W.B., (1974) Appl. Phys. Lett., 25, pp. 723-725 | ||
| 504 | |a von Trebra, R.J., Koch, T.H., (1986) J. Photochem., 35, pp. 33-46 | ||
| 504 | |a Schimitschek, E.J., Trias, J.A., Hammond, P.R., Henry, R.A., Atkins, R.L., (1976) Opt. Commun., 16, pp. 313-316 | ||
| 504 | |a Fletcher, A.N., Bliss, D.E., (1978) Appl. Phys., 16, pp. 289-295 | ||
| 504 | |a Reynolds, G.A., Drexhage, K.H., (1975) Opt. Commun., 13, pp. 222-225 | ||
| 504 | |a Nekipelova, T.D., Kurkovskaya, L.N., Levina, I.I., Shishkov, V.S., Kuzmin, V.A., (2001) Russ. Chem. Bull., 50, pp. 673-677 | ||
| 504 | |a Nekipelova, T.D., (2002) Photochem. Photobiol. Sci., 1, pp. 204-210 | ||
| 504 | |a Nekipelova, T.D., Kuzmin, V.A., (2005) High Energy Chem., 39, pp. 392-396 | ||
| 504 | |a Luche, J.L., (1978) J. Am. Chem. Soc., 100, pp. 2226-2227 | ||
| 504 | |a Jones, T.K., Zhi, L., Edwards, J.P., Tegley, C.M., West, S.J., (1997), US Pat., US5696127A; Herrmann, R., Josel, H.-P., Drexhage, K.-H., Arden-Jacob, J., (1998), US Pat., US5750409A; Wang, Q., Zimmerman, E.I., Toutchkine, A., Martin, T.D., Graves, L.M., Lawrence, D.S., (2010) ACS Chem. Biol., 5, pp. 887-895 | ||
| 504 | |a Cheng, M., Yang, X., Li, J., Chen, C., Zhao, J., Wang, Y., Sun, L., (2012) Chem. Eur. J., 18, pp. 16196-16202 | ||
| 504 | |a Anzalone, A.V., Wang, T.Y., Chen, Z., Cornish, V.W., (2013) Angew. Chem. Int. Ed., 52, pp. 650-654 | ||
| 504 | |a (2013) Angew. Chem., 125, pp. 678-682 | ||
| 504 | |a Towl, A.D.C., (2007) Inorganic Reactions and Methods, pp. 204-205. , in, Wiley, New York | ||
| 504 | |a Nishiyama, Y., Yoshida, M., Ohkawa, S., Hamanaka, S., (1991) J. Org. Chem., 56, pp. 6720-6722 | ||
| 504 | |a Nagao, Y., Fujita, E., Kohno, T., Yagi, M., (1981) Chem. Pharm. Bull., 29, pp. 3202-3207 | ||
| 504 | |a Boyarskiy, V.P., Belov, V.N., Medda, R., Hein, B., Bossi, M., Hell, S.W., (2008) Chem. Eur. J., 14, pp. 1784-1792 | ||
| 504 | |a Rechthaler, K., Köhler, G., (1994) Chem. Phys., 189, pp. 99-116 | ||
| 504 | |a Nad, S., Pal, H., (2001) J. Phys. Chem. A, 105, pp. 1097-1106 | ||
| 504 | |a Jones, G., Jackson, W.R., Choi, C., Bergmark, W.R., (1985) J. Phys. Chem., 89, pp. 294-300 | ||
| 504 | |a http://www.abberior.com/fileadmin/user-upload/documents/Down-loads/Application-Notes/20120316-Labeling-Protocol.pdf; Eggeling, C., Widengren, J., Rigler, R., Seidel, C.A.M., (1998) Anal. Chem., 70, pp. 2651-2659 | ||
| 504 | |a Schmidt, R., Wurm, C.A., Jakobs, S., Engelhardt, J., Egner, A., Hell, S.W., (2008) Nat. Methods, 5, pp. 539-544 | ||
| 504 | |a Kolmakov, K., Wurm, C.A., Hennig, R., Rapp, E., Jakobs, S., Belov, V.N., Hell, S.W., (2012) Chem. Eur. J., 18, pp. 12986-12998 | ||
| 504 | |a Oddoux, S., Zaal, K.J., Tate, V., Kenea, A., Nandkeolyar, S.A., Reid, E., Liu, W., Ralston, E., (2013) J. Cell Biol., 203, pp. 205-213 | ||
| 504 | |a Head, B.P., Patel, H.H., Roth, D.M., Murray, F., Swaney, J.S., Niesman, I.R., Farquhar, M.G., Insel, P.A., (2006) J. Biol. Chem., 281, pp. 26391-26399 | ||
| 504 | |a Butkevich, A.N., Mitronova, G.Y., Sidenstein, S.C., Klocke, J.L., Kamin, D., Meineke, D.N.H., D'Este, E., Hell, S.W., (2016) Angew. Chem. Int. Ed., 55, pp. 3290-3294 | ||
| 504 | |a (2016) Angew. Chem., 128, pp. 3350-3355 | ||
| 520 | 3 | |a Large Stokes-shift coumarin dyes with an O-phosphorylated 4-(hydroxymethyl)-2,2-dimethyl-1,2,3,4-tetrahydroquinoline fragment emitting in the blue, green, and red regions of the visible spectrum were synthesized. For this purpose, N-substituted and O-protected 1,2-dihydro-7-hydroxy-2,2,4-trimethylquinoline was oxidized with SeO2to the corresponding α,β-unsaturated aldehyde and then reduced with NaBH4in a “one-pot” fashion to yield N-substituted and 7-O-protected 4-(hydroxymethyl)-7-hydroxy-2,2-dimethyl-1,2,3,4-tetrahydroquinoline as a common precursor to all the coumarin dyes reported here. The photophysical properties of the new dyes (“reduced coumarins”) and 1,2-dihydroquinoline analogues (formal precursors) with a trisubstituted C=C bond were compared. The “reduced coumarins” were found to be more photoresistant and brighter than their 1,2-dihydroquinoline counterparts. Free carboxylate analogues, as well as their antibody conjugates (obtained from N-hydroxysuccinimidyl esters) were also prepared. All studied conjugates with secondary antibodies afforded high specificity and were suitable for fluorescence microscopy. The red-emitting coumarin dye bearing a betaine fragment at the C-3-position showed excellent performance in stimulation emission depletion (STED) microscopy. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |l eng | |
| 593 | |a Department of NanoBiophotonics, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, Göttingen, 37077, Germany | ||
| 593 | |a Laboratorio de Nanoscopias Fotonicas, INQUIMAE-DQIAyQF (FCEyN), Universidad de Buenos Aires & Conicet, Buenos Aires, Argentina | ||
| 593 | |a Institute for Organic and Biomolecular Chemistry, Georg-August University, Tammannstrasse 2, Göttingen, 37077, Germany | ||
| 593 | |a Heart Research Center Göttingen, Department of Cardiology & Pulmonology, University Medical Center Göttingen, Göttingen, 37077, Germany | ||
| 690 | 1 | 0 | |a BIOCONJUGATION |
| 690 | 1 | 0 | |a COUMARINS |
| 690 | 1 | 0 | |a DYES/PIGMENTS |
| 690 | 1 | 0 | |a FLUORESCENCE |
| 690 | 1 | 0 | |a STED MICROSCOPY |
| 690 | 1 | 0 | |a ANTIBODIES |
| 690 | 1 | 0 | |a CARBOXYLATION |
| 690 | 1 | 0 | |a FLUORESCENCE |
| 690 | 1 | 0 | |a FLUORESCENCE MICROSCOPY |
| 690 | 1 | 0 | |a PHOSPHORYLATION |
| 690 | 1 | 0 | |a STIMULATED EMISSION |
| 690 | 1 | 0 | |a SUBSTITUTION REACTIONS |
| 690 | 1 | 0 | |a ANTIBODY CONJUGATE |
| 690 | 1 | 0 | |a BIO-CONJUGATION |
| 690 | 1 | 0 | |a COUMARINS |
| 690 | 1 | 0 | |a DYES/PIGMENTS |
| 690 | 1 | 0 | |a PHOTOPHYSICAL PROPERTIES |
| 690 | 1 | 0 | |a SECONDARY ANTIBODIES |
| 690 | 1 | 0 | |a STED MICROSCOPIES |
| 690 | 1 | 0 | |a UNSATURATED ALDEHYDES |
| 690 | 1 | 0 | |a METHANOL |
| 690 | 1 | 0 | |a COUMARIN DERIVATIVE |
| 690 | 1 | 0 | |a FLUORESCENT DYE |
| 690 | 1 | 0 | |a QUINOLINE DERIVATIVE |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a FLUORESCENCE MICROSCOPY |
| 690 | 1 | 0 | |a PHOSPHORYLATION |
| 690 | 1 | 0 | |a SYNTHESIS |
| 690 | 1 | 0 | |a COUMARINS |
| 690 | 1 | 0 | |a FLUORESCENT DYES |
| 690 | 1 | 0 | |a MICROSCOPY, FLUORESCENCE |
| 690 | 1 | 0 | |a PHOSPHORYLATION |
| 690 | 1 | 0 | |a QUINOLINES |
| 700 | 1 | |a Sednev, M.V. | |
| 700 | 1 | |a Bossi, M.L. | |
| 700 | 1 | |a Hebisch, E. | |
| 700 | 1 | |a Frauendorf, H. | |
| 700 | 1 | |a Lehnart, S.E. | |
| 700 | 1 | |a Belov, V.N. | |
| 700 | 1 | |a Hell, S.W. | |
| 773 | 0 | |d Wiley-VCH Verlag, 2016 |g v. 22 |h pp. 11631-11642 |k n. 33 |p Chem. Eur. J. |x 09476539 |w (AR-BaUEN)CENRE-83 |t Chemistry - A European Journal | |
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| 856 | 4 | 0 | |u https://doi.org/10.1002/chem.201601252 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_09476539_v22_n33_p11631_Nizamov |y Handle |
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