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. 2019 Apr 9;5(4):e01405.
doi: 10.1016/j.heliyon.2019.e01405. eCollection 2019 Apr.

Detailed chemical characterization and molecular modeling of serotonin inclusion complex with unmodified β-cyclodextrin

F Fateminasab  1 , A K Bordbar  1 , S Shityakov  2
Affiliations

Detailed chemical characterization and molecular modeling of serotonin inclusion complex with unmodified β-cyclodextrin

F Fateminasab et al. Heliyon. .

Abstract

In this study, we analyzed the capability of unmodified β-cyclodextrin (β-CD) to form the stable complex with serotonin hydrochloride (SER), as an important neurotransmitter in the brain. The stable β-CD: SER formulation was prepared and characterized using spectroscopic, thermal, molecular docking, and molecular dynamics techniques, revealing the phenomenon of H-bond formations and the domination of hydrophobic forces between the host molecule and its guest via the amine group of SER and the narrow side of β-CD. The complexation mechanism was mainly enthalpy-driven, representing the improvement in SER photo-stability. Overall, the results highlighted the possibility to use this formulation with improved stability in clinical practice for treatment and prevention of various depressive conditions, such as anxiety disorders.

Keywords: Pharmaceutical chemistry; Physical chemistry; Theoretical chemistry.

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Figures

Fig. 1
Fig. 1
The phase solubility diagram in PBS (10 mM pH 7.4) and at various temperatures. b) The van't Hoff plot for the formation of β-CD: SER IC (R2 = 0.996).
Fig. 2
Fig. 2
FTIR for a) β-CD, b) SER, c) physical mixture (β-CD: SER) and d) β-CD: SER IC.
Fig. 3
Fig. 3
1H-NMR belonging a) β-CD, b) SER and c) β-CD: SER IC in D2O.
Fig. 4
Fig. 4
FE-SEM micrograms for a) β-CD, b) SER and c) β-CD: SER IC.
Fig. 5
Fig. 5
XRD for a) β-CD, b) SER, c) physical mixture (β-CD: SER) and d) β-CD: SER IC.
Fig. 6
Fig. 6
The TGA (a) and DTG (b) curves for β-CD (dash line, - - -), SER (dot line, …..) and β-CD: SER IC (line, —).
Fig. 7
Fig. 7
The ICD spectra of β-CD (dash line, - - -), SER (dot line, …..) and β-CD: SER IC (line, —) at 250–350 nm in PBS (10 mM, pH 7.4).
Fig. 8
Fig. 8
Molecular docking for β-CD: SER IC.
Fig. 9
Fig. 9
a) Snapshots of in the free β-CD and β-CD: SER IC in 0, 10, 25, 40 and 50 ns. b) RMSD of free β-CD and β-CD: SER IC during 50 ns simulation time.
Fig. 10
Fig. 10
a) A D-glucose unit in of β-CD (n = 7), b) SER molecule.
Fig. 11
Fig. 11
a) RDF of waters around the oxygen atoms (O2, O3, O4, O5 and O6) for a) free β-CD and b) β-CD: SER IC.
Fig. 12
Fig. 12
The Distance between O4 of β-CD and SER in water solvent during 50 ns simulation time.
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