Inclusion complexes of nabumetone with β-cyclodextrins: Spectroscopic, spectrometric and calorimetric studies in solution

Klarić, David; Kelrajter, Melita; Čikoš, Ana; Budimir, Ana; Galić, Nives (2024) Inclusion complexes of nabumetone with β-cyclodextrins: Spectroscopic, spectrometric and calorimetric studies in solution. Journal of Molecular Liquids, 397 . ISSN 0167-7322

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Abstract

The complexation of nabumetone (NAB) with various cyclodextrins (CDs): β-cyclodextrin (β-CD), hydroxypropylβ-CD (HPβCD), randomly methylated β-CD (RMβCD), and sulfobutylether sodium salt β-CD (SBEβCD), was investigated as a mean to increase the poor solubility of NAB both in water and simulated biorelevant media (pH = 1.0 (HCl) and pH = 4.5 and 6.8 (phosphate buffer)). An approximately 170 times increase in NAB solubility was achieved for SBEβCD in all media. The formation of 1:1 complexes was confirmed by phase-solubility measurements, spectrofluorimetric titration and high resolution mass spectrometry. Additionally, isothermal microcalorimetric titrations were employed to determine thermodynamic parameters (lgK, ΔrG0, ΔrH0, ΔrS0). Stability constants (lgK = 3.42; 3.41; 3.47 and 3.62 for NAB complexes with β-CD, HPβCD, RMβCD, and SBEβCD, respectively) agree with those obtained by phase-solubility experiments and spectrofluorimetric titrations. The inclusion was enthalpy and entropy favorable. NMR analyses showed two possible orientations of NAB in the β-CD cavity simultaneously exist in the solution, with a naphthalene ring inside the β-CD cavity and methoxy or butanone substituent oriented towards the narrow β-CD rim. All experimental results are in good agreement with those based on molecular modeling previously reported in the literature.

Item Type:	Article
Uncontrolled Keywords:
Subjects:	NATURAL SCIENCES
Divisions:	NMR Center
Projects:	Project title Project leader Project code Project type Priprava, karakterizacija i biokompatibilnost novih supramolekulskih kompleksa lijek/ciklodekstrin i lijek/dekstrinske nanospužve s poboljšanim svojstvima Nives Galić IP-2022-10-6033 HRZZ
Depositing User:	Ana Čikoš
Date Deposited:	16 Dec 2025 12:43
URI:	http://fulir.irb.hr/id/eprint/10463
DOI:	10.1016/j.molliq.2024.124152

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