Preparation and characterization of spiro-acridine derivative and 2-hydroxypropyl-β-cyclodextrin inclusion complex

•Spiro-acridine AMTAC-01 was complexed with 2-hydroxypropryl-β-cyclodextrin (HPβCD).•HPβCD complexed with AMTAC-01 in a 1:1 molar ratio as shown by molecular modeling.•¹H NMR, FT-IR, Raman, SEM, XRD, and fluorescence confirmed the inclusion complex. The spiro-acridine derivative (E)-1′-(benzylidenea...

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Published inJournal of molecular structure Vol. 1222; p. 128945
Main Authors Melo, Camila de Oliveira, Rodrigues, Maria Salete da Silva, da Silva, Marcus Vinicius Santos, Marcelino, Henrique Rodrigues, Rabello, Marcelo Montenegro, de Moura, Ricardo Olímpio, Eleamen Oliveira, Elquio
Format Journal Article
LanguageEnglish
Published Elsevier B.V 15.12.2020
Subjects
Acridine derivative
Fluorescence spectrophotometry
Inclusion complex
Molecular modeling
NMR spectroscopy
Acridine derivative
Fluorescence spectrophotometry
NMR spectroscopy
Molecular modeling
Inclusion complex
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Abstract •Spiro-acridine AMTAC-01 was complexed with 2-hydroxypropryl-β-cyclodextrin (HPβCD).•HPβCD complexed with AMTAC-01 in a 1:1 molar ratio as shown by molecular modeling.•¹H NMR, FT-IR, Raman, SEM, XRD, and fluorescence confirmed the inclusion complex. The spiro-acridine derivative (E)-1′-(benzylideneamino)-5′-oxo-1′,5′-dihydro-10H-spiro[acridine-9,2′-pyrrole]-4-carbonitrile (AMTAC-01) is a synthetic compound with limited water solubility, which restricts its physiological activities and therapeutic applications. Hence, we investigated the complexation of AMTAC-01 with 2-hydroxypropyl‑β‑cyclodextrin (HPβCD) using the freeze-drying method. Complex formation was characterized by scanning electron microscopy, X-ray diffractometry(XRD), nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, Raman spectroscopy, and fluorescence spectrophotometry. Additionally, molecular modeling and phase solubility studies were performed. Molecular modeling demonstrated the most stable inclusion model, and phase solubility studies indicated that AMTAC-01 and HPβCD formed a 1:1 inclusion complex with an apparent stability constant of 1145.3 M − 1. XRD and spectroscopy results suggest intermolecular interactions between AMTAC-01 and HPβCD, with the formation of a 1:1 inclusion complex demonstrating an amorphous pattern and alterations in band distribution intensities compared with free drug. [Display omitted]
AbstractList •Spiro-acridine AMTAC-01 was complexed with 2-hydroxypropryl-β-cyclodextrin (HPβCD).•HPβCD complexed with AMTAC-01 in a 1:1 molar ratio as shown by molecular modeling.•¹H NMR, FT-IR, Raman, SEM, XRD, and fluorescence confirmed the inclusion complex. The spiro-acridine derivative (E)-1′-(benzylideneamino)-5′-oxo-1′,5′-dihydro-10H-spiro[acridine-9,2′-pyrrole]-4-carbonitrile (AMTAC-01) is a synthetic compound with limited water solubility, which restricts its physiological activities and therapeutic applications. Hence, we investigated the complexation of AMTAC-01 with 2-hydroxypropyl‑β‑cyclodextrin (HPβCD) using the freeze-drying method. Complex formation was characterized by scanning electron microscopy, X-ray diffractometry(XRD), nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, Raman spectroscopy, and fluorescence spectrophotometry. Additionally, molecular modeling and phase solubility studies were performed. Molecular modeling demonstrated the most stable inclusion model, and phase solubility studies indicated that AMTAC-01 and HPβCD formed a 1:1 inclusion complex with an apparent stability constant of 1145.3 M − 1. XRD and spectroscopy results suggest intermolecular interactions between AMTAC-01 and HPβCD, with the formation of a 1:1 inclusion complex demonstrating an amorphous pattern and alterations in band distribution intensities compared with free drug. [Display omitted]
ArticleNumber 128945
Author Melo, Camila de Oliveira
Marcelino, Henrique Rodrigues
Rodrigues, Maria Salete da Silva
da Silva, Marcus Vinicius Santos
de Moura, Ricardo Olímpio
Eleamen Oliveira, Elquio
Rabello, Marcelo Montenegro
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Fluorescence spectrophotometry
NMR spectroscopy
Molecular modeling
Inclusion complex
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Snippet •Spiro-acridine AMTAC-01 was complexed with 2-hydroxypropryl-β-cyclodextrin (HPβCD).•HPβCD complexed with AMTAC-01 in a 1:1 molar ratio as shown by molecular...
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SubjectTerms Acridine derivative
Fluorescence spectrophotometry
Inclusion complex
Molecular modeling
NMR spectroscopy
Title Preparation and characterization of spiro-acridine derivative and 2-hydroxypropyl-β-cyclodextrin inclusion complex
URI https://dx.doi.org/10.1016/j.molstruc.2020.128945
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