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Synthesis of (E)-Ethyl-4-(2-(furan-2-ylmethylene)hydrazinyl)benzoate, crystal structure, and studies of its interactions with human serum albumin by spectroscopic fluorescence and molecular docking methods

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Synthesis of (E)-Ethyl-4-(2-(furan-2-ylmethylene)hydrazinyl)benzoate, crystal structure, and studies of its interactions with human serum albumin by spectroscopic fluorescence and molecular docking methods. / Morales-Toyo, Miguel; Glidewell, Christopher; Bruno-Colmenares, Julia; Cubillán, Néstor; Sánchez-Colls, Ronald; Alvarado, Ysaias; Restrepo, Jelen.

In: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, Vol. In press, 12.03.2019.

Research output: Contribution to journalArticlepeer-review

Harvard

Morales-Toyo, M, Glidewell, C, Bruno-Colmenares, J, Cubillán, N, Sánchez-Colls, R, Alvarado, Y & Restrepo, J 2019, 'Synthesis of (E)-Ethyl-4-(2-(furan-2-ylmethylene)hydrazinyl)benzoate, crystal structure, and studies of its interactions with human serum albumin by spectroscopic fluorescence and molecular docking methods', Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, vol. In press. https://doi.org/10.1016/j.saa.2019.03.028

APA

Morales-Toyo, M., Glidewell, C., Bruno-Colmenares, J., Cubillán, N., Sánchez-Colls, R., Alvarado, Y., & Restrepo, J. (2019). Synthesis of (E)-Ethyl-4-(2-(furan-2-ylmethylene)hydrazinyl)benzoate, crystal structure, and studies of its interactions with human serum albumin by spectroscopic fluorescence and molecular docking methods. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, In press. https://doi.org/10.1016/j.saa.2019.03.028

Vancouver

Morales-Toyo M, Glidewell C, Bruno-Colmenares J, Cubillán N, Sánchez-Colls R, Alvarado Y et al. Synthesis of (E)-Ethyl-4-(2-(furan-2-ylmethylene)hydrazinyl)benzoate, crystal structure, and studies of its interactions with human serum albumin by spectroscopic fluorescence and molecular docking methods. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy. 2019 Mar 12;In press. https://doi.org/10.1016/j.saa.2019.03.028

Author

Morales-Toyo, Miguel ; Glidewell, Christopher ; Bruno-Colmenares, Julia ; Cubillán, Néstor ; Sánchez-Colls, Ronald ; Alvarado, Ysaias ; Restrepo, Jelen. / Synthesis of (E)-Ethyl-4-(2-(furan-2-ylmethylene)hydrazinyl)benzoate, crystal structure, and studies of its interactions with human serum albumin by spectroscopic fluorescence and molecular docking methods. In: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy. 2019 ; Vol. In press.

Bibtex - Download

@article{26b17516e8a64d9cb90f5f8531c84d78,
title = "Synthesis of (E)-Ethyl-4-(2-(furan-2-ylmethylene)hydrazinyl)benzoate, crystal structure, and studies of its interactions with human serum albumin by spectroscopic fluorescence and molecular docking methods",
abstract = "A novel hydrazone, (E)-Ethyl-4-(2-(furan-2-ylmethylene)hydrazinyl)benzoate (EFHB), has been synthesized and characterized by FT-IR, NMR and Mass spectroscopy, and X-ray diffraction; compound crystallized as translucent light yellow thin plates. EFHB was studied for their binding to human serum albumin (HSA) using the fluorescence quench titration method. Molecular docking was also performed to get a more detailed insight into their interaction with HSA at the binding site. Addition of this hydrazone to HSA produced significant fluorescence quenching and splitting of emission spectra of HSA through static quenching mechanism with binding constants of about 104 M−1 at 292.15, 298.15, 304.15 and 310.15 K. According to the synchronous fluorescence, tryptophan and tyrosine residues of the protein are most perturbed by the binding process. Thermodynamic parameters ΔG, ΔH, and ΔS were got and the main sort of acting force between EFHB and HSA was studied. Results of molecular docking have shown that EFHB binds to subdomain IIA of HSA mainly by hydrophobic interaction, energy binding are in good agreement with those obtained by fluorescence study (ΔGthe = −7.32 ± 0.09 kcal mol−1 and ΔGexp = −6.76 ± 0.03 kcal mol−1).",
keywords = "Hydrazone derivative, Crystal structure, HSA, Molecular docking, Fluorescence spectroscopy",
author = "Miguel Morales-Toyo and Christopher Glidewell and Julia Bruno-Colmenares and N{\'e}stor Cubill{\'a}n and Ronald S{\'a}nchez-Colls and Ysaias Alvarado and Jelen Restrepo",
note = "The authors thank Fondo Nacional de Ciencia Tecnolog{\'i}a e Innovaci{\'o}n (FONACIT Proyecto de apoyo a Grupos No. G-2005000403). Proyecto 1063, Instituto Venezolano de Investigaciones Cient{\'i}ficas (IVIC).",
year = "2019",
month = mar,
day = "12",
doi = "10.1016/j.saa.2019.03.028",
language = "English",
volume = "In press",
journal = "Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy",
issn = "1386-1425",
publisher = "Elsevier",

}

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TY - JOUR

T1 - Synthesis of (E)-Ethyl-4-(2-(furan-2-ylmethylene)hydrazinyl)benzoate, crystal structure, and studies of its interactions with human serum albumin by spectroscopic fluorescence and molecular docking methods

AU - Morales-Toyo, Miguel

AU - Glidewell, Christopher

AU - Bruno-Colmenares, Julia

AU - Cubillán, Néstor

AU - Sánchez-Colls, Ronald

AU - Alvarado, Ysaias

AU - Restrepo, Jelen

N1 - The authors thank Fondo Nacional de Ciencia Tecnología e Innovación (FONACIT Proyecto de apoyo a Grupos No. G-2005000403). Proyecto 1063, Instituto Venezolano de Investigaciones Científicas (IVIC).

PY - 2019/3/12

Y1 - 2019/3/12

N2 - A novel hydrazone, (E)-Ethyl-4-(2-(furan-2-ylmethylene)hydrazinyl)benzoate (EFHB), has been synthesized and characterized by FT-IR, NMR and Mass spectroscopy, and X-ray diffraction; compound crystallized as translucent light yellow thin plates. EFHB was studied for their binding to human serum albumin (HSA) using the fluorescence quench titration method. Molecular docking was also performed to get a more detailed insight into their interaction with HSA at the binding site. Addition of this hydrazone to HSA produced significant fluorescence quenching and splitting of emission spectra of HSA through static quenching mechanism with binding constants of about 104 M−1 at 292.15, 298.15, 304.15 and 310.15 K. According to the synchronous fluorescence, tryptophan and tyrosine residues of the protein are most perturbed by the binding process. Thermodynamic parameters ΔG, ΔH, and ΔS were got and the main sort of acting force between EFHB and HSA was studied. Results of molecular docking have shown that EFHB binds to subdomain IIA of HSA mainly by hydrophobic interaction, energy binding are in good agreement with those obtained by fluorescence study (ΔGthe = −7.32 ± 0.09 kcal mol−1 and ΔGexp = −6.76 ± 0.03 kcal mol−1).

AB - A novel hydrazone, (E)-Ethyl-4-(2-(furan-2-ylmethylene)hydrazinyl)benzoate (EFHB), has been synthesized and characterized by FT-IR, NMR and Mass spectroscopy, and X-ray diffraction; compound crystallized as translucent light yellow thin plates. EFHB was studied for their binding to human serum albumin (HSA) using the fluorescence quench titration method. Molecular docking was also performed to get a more detailed insight into their interaction with HSA at the binding site. Addition of this hydrazone to HSA produced significant fluorescence quenching and splitting of emission spectra of HSA through static quenching mechanism with binding constants of about 104 M−1 at 292.15, 298.15, 304.15 and 310.15 K. According to the synchronous fluorescence, tryptophan and tyrosine residues of the protein are most perturbed by the binding process. Thermodynamic parameters ΔG, ΔH, and ΔS were got and the main sort of acting force between EFHB and HSA was studied. Results of molecular docking have shown that EFHB binds to subdomain IIA of HSA mainly by hydrophobic interaction, energy binding are in good agreement with those obtained by fluorescence study (ΔGthe = −7.32 ± 0.09 kcal mol−1 and ΔGexp = −6.76 ± 0.03 kcal mol−1).

KW - Hydrazone derivative

KW - Crystal structure

KW - HSA

KW - Molecular docking

KW - Fluorescence spectroscopy

U2 - 10.1016/j.saa.2019.03.028

DO - 10.1016/j.saa.2019.03.028

M3 - Article

VL - In press

JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

JF - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

SN - 1386-1425

ER -

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