European Journal of Chemistry 2019, 10(2), 175-179 | doi: https://doi.org/10.5155/eurjchem.10.2.175-179.1869 | Get rights and content

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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 | Revised: 19 May 2019 | Accepted: 20 May 2019 | Published: 30 Jun 2019 | Issue Date: June 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.


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Keywords


Fluorescent Protein Crystal structure Intermolecular Interactions UV absorption Emission Red shift

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DOI: 10.5155/eurjchem.10.2.175-179.1869

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Funding information


Kerala State Council for Science, Technology and Environment (KSCSTE), Thiruvananthapuram, India.

Citations

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[1]. Bhupendra P. Mali, Soumya Ranjan Dash, Shrikant B. Nikam, Anisha Puthuvakkal, Kumar Vanka, Kochunnoonny Manoj, Rajesh G. Gonnade
Five concomitant polymorphs of a green fluorescent protein chromophore (GFPc) analogue: understanding variations in photoluminescence with π-stacking interactions
Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials  76(5), 850, 2020
DOI: 10.1107/S2052520620010343
/

[2]. Bhupendra P. Mali, Soumya Ranjan Dash, Anupam Biswas, Kumar Vanka, Kochunnoonny Manoj, Rajesh G. Gonnade
Polymorphs of Green Fluorescence Protein Chromophore Analogue: Fluorescence Switching with Thermal Stimuli
Crystal Growth & Design  22(3), 1892, 2022
DOI: 10.1021/acs.cgd.1c01459
/

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The Supplementary Material for this article can be found online at: Supplementary files

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. 29 May. 2023
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)

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European Journal of Chemistry 2019, 10(2), 175-179 | doi: https://doi.org/10.5155/eurjchem.10.2.175-179.1869 | Get rights and content

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