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Peer-reviewedCC BYThe journal of physical chemistry. B

Thermodynamic and Structural Evidence for Higher-Order Selegiline with Carboxymethyl-β-Cyclodextrin Supramolecular Assemblies in Aqueous Solution.

  • Diego Caproni de Morais1
  • Rogério R Macedo2
  • Bianca B M Vieira1
  • Ivana Lula3
  • Juliana Fedoce Lopes2
  • Frederico B De Sousa1
  1. 1Laboratório de Sistemas Poliméricos e Supramoleculares (LSPS)-Instituto de Física e Química, Universidade Federal de Itajubá (UNIFEI), Itajubá37500-903, M G, Brazil.
  2. 2Laboratório de Química Computacional (LaQC)-Instituto de Física e Química, Universidade Federal de Itajubá (UNIFEI), Itajubá37500-903, Brazil.
  3. 3Departamento de Química-Instituto de Ciências Exatas, Universidade Federal de Minas Gerais (UFMG), Belo Horizonte31270-901, MG, Brazil.
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Abstract

The supramolecular interactions between selegiline hydrochloride (SEL) and β-cyclodextrin (βCD) derivatives were investigated through isothermal titration calorimetry (ITC), nuclear magnetic resonance (NMR), and molecular dynamics (MD) simulations. Thermodynamic analyses revealed spontaneous complex formation in aqueous solution for both βCD and carboxymethyl-β-cyclodextrin (CM-βCD), with CM-βCD exhibiting higher equilibrium constants and more favorable thermodynamic parameters. The complexation process was predominantly entropy-driven, indicating significant contributions from hydrophobic interactions and solvent reorganization. Non-integer stoichiometric values (n ≈ 1.5) obtained by ITC suggested the formation of higher-order supramolecular assemblies. NMR experiments demonstrated strong spatial correlations between the aromatic hydrogens of SEL and the cavity hydrogens of CM-βCD, supporting deep inclusion within the CD cavity. MD simulations corroborated the experimental findings and demonstrated the feasibility of a 3:2 CM-βCD:SEL supramolecular organization. Overall, the combined thermodynamic, spectroscopic, and computational results provide compelling evidence for higher-order, multi-equilibrium cyclodextrin supramolecular assemblies in aqueous solution.

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Cite

BibTeXRIS
BibTeX
@article{morais2026thermodynamic,
  title = {{Thermodynamic and Structural Evidence for Higher-Order Selegiline with Carboxymethyl-β-Cyclodextrin Supramolecular Assemblies in Aqueous Solution.}},
  author = {Diego Caproni de Morais and Rogério R Macedo and Bianca B M Vieira and Ivana Lula and Juliana Fedoce Lopes and Frederico B De Sousa},
  journal = {The journal of physical chemistry. B},
  year = {2026},
  month = sep,
  doi = {10.1021/acs.jpcb.6c03442},
  url = {https://europepmc.org/article/MED/42915342},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Thermodynamic and Structural Evidence for Higher-Order Selegiline with Carboxymethyl-β-Cyclodextrin Supramolecular Assemblies in Aqueous Solution.
AU  - Diego Caproni de Morais
AU  - Rogério R Macedo
AU  - Bianca B M Vieira
AU  - Ivana Lula
AU  - Juliana Fedoce Lopes
AU  - Frederico B De Sousa
PY  - 2026
DA  - 2026/09/01
JO  - The journal of physical chemistry. B
DO  - 10.1021/acs.jpcb.6c03442
UR  - https://europepmc.org/article/MED/42915342
AB  - The supramolecular interactions between selegiline hydrochloride (SEL) and β-cyclodextrin (βCD) derivatives were investigated through isothermal titration calorimetry (ITC), nuclear magnetic resonance (NMR), and molecular dynamics (MD) simulations. Thermodynamic analyses revealed spontaneous complex formation in aqueous solution for both βCD and carboxymethyl-β-cyclodextrin (CM-βCD), with CM-βCD exhibiting higher equilibrium constants and more favorable thermodynamic parameters. The complexation process was predominantly entropy-driven, indicating significant contributions from hydrophobic interactions and solvent reorganization. Non-integer stoichiometric values (n ≈ 1.5) obtained by ITC suggested the formation of higher-order supramolecular assemblies. NMR experiments demonstrated strong spatial correlations between the aromatic hydrogens of SEL and the cavity hydrogens of CM-βCD, supporting deep inclusion within the CD cavity. MD simulations corroborated the experimental findings and demonstrated the feasibility of a 3:2 CM-βCD:SEL supramolecular organization. Overall, the combined thermodynamic, spectroscopic, and computational results provide compelling evidence for higher-order, multi-equilibrium cyclodextrin supramolecular assemblies in aqueous solution.
SN  - 1520-6106
SN  - 1520-5207
ER  -