A study of supramolecular host–guest interaction of dothiepin and doxepin drugs with cyclodextrin macrocycles

Rajendiran, N.; Sankaranarayanan, R.; Saravanan, J.

doi:10.1016/j.molstruc.2014.03.051

Cited by 21 publications

(15 citation statements)

References 31 publications

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“…S1. Without BSA and adenine, the absorption maxima of DOT was seen at 300, 260, 218 nm, and for DOX was seen at 292, 245 s , and 210 nm, respectively (19,20).…”

Section: Resultsmentioning

confidence: 98%

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Spectroscopic, electrochemical and molecular docking studies of dothiepin and doxepin with bovine serum albumin and DNA base

Rajendiran

Thulasidhasan

2016

Luminescence

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The interaction of dothiepin (DOT) and doxepin (DOX) with bovine serum albumin (BSA) and a DNA base (adenine) was studied using UV-visible, fluorescence, attenuated total reflection-infra-red (ATR-IR), cyclic voltammetry and molecular docking methods. Strong fluorescence quenching was observed upon interaction of DOT and DOX with BSA/adenine and the mechanism suggested static quenching. Hydrophobic and hydrogen bonding interactions were the predominant intermolecular forces needed to stabilize the copolymer. Upon addition of the drugs: (i) the tautomeric equilibrium structure of the adenine was changed; and (ii) the oxidation and the reduction peaks of the adenine/BSA interaction shifted towards high and low potentials, respectively. In ATR-IR, the band shift of amides I and II indicated a change in secondary structure of BSA upon binding to DOT and DOX drugs. The reduction in voltammetric current in the presence of BSA/adenine was attributed to slow diffusion of BSA/adenine binding with DOX/DOT. The docking method indicated that the drug moiety interacted with the BSA molecule. Copyright © 2016 John Wiley & Sons, Ltd.

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“…S1. Without BSA and adenine, the absorption maxima of DOT was seen at 300, 260, 218 nm, and for DOX was seen at 292, 245 s , and 210 nm, respectively (19,20).…”

Section: Resultsmentioning

confidence: 98%

“…It is well known that adenine forms a number of tautomer compounds ( Fig. S2) that can be quickly inter-changed and are usually considered equivalent [20]. The normal Stokes shifted emission (F 1 ) is thought to originate from the excitation of the normal adenine molecule.…”

Section: Fluorescence Measurementsmentioning

confidence: 99%

Spectroscopic, electrochemical and molecular docking studies of dothiepin and doxepin with bovine serum albumin and DNA base

Rajendiran

Thulasidhasan

2016

Luminescence

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“…Semiempirical PM3 calculations show that the equimolar β-CD–IPM and β-CD–DXP inclusion complexes are thermodynamically stable; the aromatic moiety is partly included in the CD cavity [ 21 ], Table S1 . Moreover, in solution, DXP forms 1:2 inclusion complexes with α- and β-CDs such that the two aromatic A- and B-rings are embedded in the CD cavities with binding constants of 14.7–16.5 × 10 3 and 16.2–19.6 × 10 3 M −1 , as deduced from UV-vis and fluorescence data, respectively [ 22 ]. By contrast, in the gas phase, PM3 calculations suggest the energetically favorable 1:1 α-CD–DXP inclusion complex with the side chain enclosed in the cavity and maintained in position by van der Waals forces and hydrophobic interactions [ 22 ].…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, in solution, DXP forms 1:2 inclusion complexes with α- and β-CDs such that the two aromatic A- and B-rings are embedded in the CD cavities with binding constants of 14.7–16.5 × 10 3 and 16.2–19.6 × 10 3 M −1 , as deduced from UV-vis and fluorescence data, respectively [ 22 ]. By contrast, in the gas phase, PM3 calculations suggest the energetically favorable 1:1 α-CD–DXP inclusion complex with the side chain enclosed in the cavity and maintained in position by van der Waals forces and hydrophobic interactions [ 22 ]. The weak host–guest interactions are confirmed in solution for the 3:1 β-CD–DXP inclusion complex based on UV-vis and fluorescence data [ 23 ].…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Complexes of β-Cyclodextrin with Clomipramine and Doxepin: Effect of the Ring Substituent and Component of Drugs on Their Inclusion Topologies and Structural Flexibilities

Aree

2020

Pharmaceuticals

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Depression is a global threat. Tricyclic antidepressants (TCAs) are still efficacious in treating depression, albeit with more side effects. Cyclodextrins (CDs) with a suitable nanocavity are potential drug carriers and can enhance the drug bioavailability. Aiming for an atomistic understanding of the CD encapsulation facilitating the improvement of drug stability and the reduction of side effects, a comprehensive study series of the β-CD–TCA inclusion complexes through single crystal X-ray diffraction and density functional theory (DFT) calculation was undertaken. This work reports the supramolecular complexes of β-CD with two pivotal TCAs, clomipramine (CPM; 1) and doxepin (DXP; 2). The different inclusion topologies of the β-CD–TCA complexes were notable. X-ray analysis revealed that, in 1, the CPM B-ring (without chloro group) was entrapped in the β-CD cavity, whereas, in 2, the E-DXP A-ring and the Z-DXP B-ring were disordered in the cavity, yielding energetically favorable complexes primarily maintained by intermolecular C–H⋯π interactions, as indicated by DFT calculation. Because both wings of TCAs were similar, an alternative inclusion scenario of the A-ring was evidenced crystallographically in four other TCA complexes. The enhanced TCA thermodynamic stabilities via CD inclusion complexation helped to reduce the side effects and to increase the bioavailability. Moreover, the scrutinization of six TCAs in different lattice circumstances revealed the greater TCA structural flexibilities for their optimum pharmacological activity while binding with proteins.

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“…CD drug delivery systems, allow for encapsulation of small drug molecules as well as large biomolecules (Challa, Ahuja, Ali, & Khar, ; Davis & Brewster, ; Del Valle, ; Rajewski & Stella, ; Stella & Rajewski, ). The antidepressants, dothiepin and doxepin formed 1:2 inclusion nanostructures with α‐and β‐CDs and assemble into sphere and agglomerated structures (Rajendiran, Sankaranarayanan, & Saravanan, ). More complicated systems, involving the ternary complex “Guest 2/(Guest 1/γ‐CD)” permitted to load two different drugs at the same time; the first guest is located in the CD cavity, and the second guest is incorporated into the intermolecular spaces between CD channels (N. Liu, Higashi, Ueda, & Moribe, ).…”

Section: Oligosaccharidesmentioning

confidence: 99%

Carbohydrate‐based nanomaterials for biomedical applications

Gim

Zhu

Seeberger

et al. 2019

WIREs Nanomed Nanobiotechnol

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Carbohydrates are abundant biomolecules, with a strong tendency to form supramolecular networks. A host of carbohydrate-based nanomaterials have been exploited for biomedical applications. These structures are based on simple monoor disaccharides, as well as on complex, polymeric systems. Chemical modifications serve to tune the shapes and properties of these materials. In particular, carbohydrate-based nanoparticles and nanogels were used for drug delivery, imaging, and tissue engineering applications. Due to the reversible nature of the assembly, often based on a combination of hydrogen bonding and hydrophobic interactions, carbohydrate-based materials are valuable substrates for the creations of responsive systems. Herein, we review the current research on carbohydratebased nanomaterials, with a particular focus on carbohydrate assembly. We will discuss how these systems are formed and how their properties are tuned. Particular emphasis will be placed on the use of carbohydrates for biomedical applications.

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A study of supramolecular host–guest interaction of dothiepin and doxepin drugs with cyclodextrin macrocycles

Cited by 21 publications

References 31 publications

Spectroscopic, electrochemical and molecular docking studies of dothiepin and doxepin with bovine serum albumin and DNA base

Spectroscopic, electrochemical and molecular docking studies of dothiepin and doxepin with bovine serum albumin and DNA base

Supramolecular Complexes of β-Cyclodextrin with Clomipramine and Doxepin: Effect of the Ring Substituent and Component of Drugs on Their Inclusion Topologies and Structural Flexibilities

Carbohydrate‐based nanomaterials for biomedical applications

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