European Journal of Chemistry 2019, 10(2), 175-179. doi:10.5155/eurjchem.10.2.175-179.1869

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


Anisha Puthuvakkal (1) orcid , Kochunnoonny Manoj (2,*) orcid

(1) Photosciences and Photonics, Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Thiruvananthapuram 695019, India
(2) Photosciences and Photonics, Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Thiruvananthapuram 695019, India
(*) Corresponding Author

Received: 10 Apr 2019, Accepted: 20 May 2019, Published: 30 Jun 2019

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.


Keywords


Fluorescent Protein Crystal structure Intermolecular Interactions UV absorption Emission Red shift

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.10.2.175-179.1869

Article Metrics


This Abstract was viewed 68 times | PDF Article downloaded 51 times

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


How to cite


Puthuvakkal, A.; Manoj, K. Eur. J. Chem. 2019, 10(2), 175-179. doi:10.5155/eurjchem.10.2.175-179.1869
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(2), 175-179. doi:10.5155/eurjchem.10.2.175-179.1869
Puthuvakkal, A., & Manoj, K. (2019). 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. European Journal of Chemistry, 10(2), 175-179. doi:10.5155/eurjchem.10.2.175-179.1869
Puthuvakkal, Anisha, & Kochunnoonny Manoj. "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." European Journal of Chemistry [Online], 10.2 (2019): 175-179. Web. 20 Aug. 2019
Puthuvakkal, Anisha, AND Manoj, Kochunnoonny. "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" European Journal of Chemistry [Online], Volume 10 Number 2 (30 June 2019)

DOI Link: https://doi.org/10.5155/eurjchem.10.2.175-179.1869

Refbacks

  • There are currently no refbacks.




Copyright (c) 2019 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/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 (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).


© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.