European Journal of Chemistry

Crystal structure and spectral studies of green fluorescent protein (GFP) chromophore analogue ethyl 2-[(4Z)-(6-hydroxy naphthalen-2-yl) methylene)-2-methyl-5-oxo-4,5-di hydro-1H-imidazol-1-yl] acetate

Crossmark


Main Article Content

Anisha Puthuvakkal
Kochunnoonny Manoj

Abstract

Synthetically modified green fluorescent protein chromophore derivative was prepared, its crystal structure and spectral properties were studied. Crystal data for C19H18N2O4: triclinic, space group P-1 (no. 2), a = 8.2506(17) Å, b = 11.934(2) Å, c = 17.461(4) Å, α = 102.89(3)°,   β = 94.62(3)°, γ = 96.68(3)°, V = 1654.5(6) Å3, Z = 4, T = 173(2) K, μ(MoKα) = 0.096 mm-1, Dcalc = 1.358 g/cm3, 7227 reflections measured (4.722° ≤ 2Θ ≤ 53.996°), 7227 unique (Rint = 0.0453, Rsigma = 0.0662) which were used in all calculations. The final R1 was 0.0561 (I > 2σ(I)) and wR2 was 0.1658 (all data). The single crystal structure showed, the benzylidine moiety adopts Z-conformation in solid state and the molecules were associated by various O−H···O and C−H···O non-covalent interactions. The UV absorption-emission spectral analysis indicated that a significant red shift of emission observed at alkaline pH indicating its utility for live cell imaging applications.


icon graph This Abstract was viewed 1526 times | icon graph Article PDF downloaded 586 times icon graph Article CIF FILE downloaded 0 times

How to Cite
(1)
Puthuvakkal, A.; Manoj, K. Crystal Structure and Spectral Studies of Green Fluorescent Protein (GFP) Chromophore Analogue Ethyl 2-[(4Z)-(6-Hydroxy Naphthalen-2-Yl) Methylene)-2-Methyl-5-Oxo-4,5-Di Hydro-1H-Imidazol-1-Yl] Acetate. Eur. J. Chem. 2019, 10, 175-179.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Shimomura, FEBS Lett. 1979, 104, 220-222.
https://doi.org/10.1016/0014-5793(79)80818-2

[2]. Zimmer, M. Chem. Rev. 2002, 102, 759-782.
https://doi.org/10.1021/cr010142r

[3]. Giepmans, B. N. G.; Adams, S. R.; Ellisman, M. H.; Tsien, R. Y. Science 2006, 312, 217-224.
https://doi.org/10.1126/science.1124618

[4]. Chalfie, M. Angew. Chem. Int. Ed. 2009, 48, 5603-5611.
https://doi.org/10.1002/anie.200902040

[5]. Chudakov, D. M.; Matz, M. V.; Lukyanov, S.; Lukyanov, K. A. Physiol. Rev. 2010, 90, 1103-1163.
https://doi.org/10.1152/physrev.00038.2009

[6]. Chang, J.; Chen, X.; Glass, Z.; Gao, F.; Mao, L.; Wang, M.; Xu, Q. Acc. Chem. Res. 2019, 52, 665-675.
https://doi.org/10.1021/acs.accounts.8b00493

[7]. Kneen, M.; Farinas, J.; Li, Y.; Verkman, A. S. Biophys. J. 1998, 74, 1591-1599.
https://doi.org/10.1016/S0006-3495(98)77870-1

[8]. Tamura, T.; Hamachi, I. ACS Chem. Biol. 2014, 9, 2708-2717.
https://doi.org/10.1021/cb500661v

[9]. Walker, C. L.; Konstantin A Lukyanov, K. A.; Yampolsky, I. V.; Mishin, A. S.; Bommarius, A. S.; Duraj-Thatte, A. M.; Azizi, B.; Tolbert, L. M.; Solntsev, K. M. Curr. Opin. Chem. Biol. 2015, 27, 64-74.
https://doi.org/10.1016/j.cbpa.2015.06.002

[10]. Wang, Z.; Luo, Y.; Xie, X.; Hu, X.; Song, H.; Zhao, Y.; Shi, J.; Wang, L.; Glinsky, G.; Chen, N.; Lal, R.; Fan, C. Angew. Chem. Int. Ed. 2018, 57, 972-976.
https://doi.org/10.1002/anie.201707795

[11]. Meech, S. R. Chem. Soc. Rev. 2009, 39, 2922-2934.
https://doi.org/10.1039/b820168b

[12]. Tolbert, L. M.; Baldridge, A.; Kowalik, J.; Solntsev, K. M. Acc. Chem. Res. 2010, 45, 171-181.
https://doi.org/10.1021/ar2000925

[13]. Chatterjee, T.; Lacombat, F.; Yadav, D.; Mandal, M.; Plaza, P.; Espagne, A.; Mandal, P. K. J. Phys. Chem. B. 2016, 120, 9716-9722.
https://doi.org/10.1021/acs.jpcb.6b05795

[14]. Dong, J.; Abulwerdi, F.; Baldridge, A.; Kowalik, J.; Solntsev, K. M.; Tolbert, L. M. J. Am. Chem. Soc. 2008, 130, 14096-14098.
https://doi.org/10.1021/ja803416h

[15]. Wang, D.; Merz, T.; Van Gunsteren, W. F. Phys. Chem. Chem. Phys. 2010, 12, 11051-11061.
https://doi.org/10.1039/c0cp00181c

[16]. Baldridge, A.; Solntsev, K. M.; Song, C.; Tanioka, T.; Kowalik, J.; Hardcastle, K.; Tolbert, L. M. Chem. Commun. 2010, 46, 5686-5688.
https://doi.org/10.1039/b927313a

[17]. Wu, L.; Burgess, K. J. Am. Chem. Soc. 2008, 130, 4089-4096.
https://doi.org/10.1021/ja710388h

[18]. Chen, K.; Cheng, Y.; Lai, C.; Hsu, C.; Ho, M.; Lee, G.; Chou, P. J. Am. Chem. Soc. 2007, 129, 4534-4535.
https://doi.org/10.1021/ja070880i

[19]. Dong, J.; Solntsev, K. M.; Tolbert, L. M. J. Am. Chem. Soc. 2009, 131, 662-670.
https://doi.org/10.1021/ja806962e

[20]. Hsu, Y.; Chen, Y.; Tseng, H.; Zhang, Z.; Shen, J.; Chuang, W.; Lin, T.; Lee, C.; Hung, W.; Hong, B.; Liu, S.; Chou, P. J. Am. Chem. Soc. 2014, 136, 11805-11812.
https://doi.org/10.1021/ja5062856

[21]. Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA, 2011.

[22]. Sheldrick, G. M. Acta Cryst. A 2015, 71, 3-8.
https://doi.org/10.1107/S2053229614024218

[23]. Sheldrick, G. M. Acta Cryst. C 2015, 71, 3-8.
https://doi.org/10.1107/S2053229614024218

[24]. Manoj, K.; Gonnade, R. G.; Bhadbhade, M. M.; Shashidhar, M. S. Cryst. Growth Des. 2006, 6, 1485-1492.

[25]. Manoj, K.; Gonnade, R. G.; Bhadbhade, M. M.; Shashidhar, M. S. Acta Crystallogr. C 2009, 65, o335-o338.
https://doi.org/10.1107/S0108270109017211

[26]. Manoj, K.; Gonnade, R. G.; Bhadbhade, M. M.; Shashidhar, M. S. CrystEngComm 2012, 14, 1716-1722.
https://doi.org/10.1039/C2CE06287A

Supporting Agencies

Kerala State Council for Science, Technology and Environment (KSCSTE), Thiruvananthapuram, India.
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).