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Inclusion complexation of naproxen with cyclosophoraoses and succinylated cyclosophoraoses in different pH environments

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Abstract

Cyclosophoraoses [cyclic β-(1,2)-glucan, Cys] isolated from Rhizobium leguminosarum biovar trifolii TA-1 have unique structures and high solubility, which make it a potent solubilizer for host–guest inclusion complexation. Succinylated cyclosophorasoses (S-Cys) were also synthesized by chemically modifying isolated cyclosophoraoses. In ultraviolet-visible studies using naproxen (NAP), Cys was shown to form the most stable complexes with NAP (K 1:1 = 2457.9 M−1), which was followed by the negatively charged S-Cys (K 1:1 = 357.1 M−1) at pH 3.4. A further strong reduction in the complex stability constant was observed at pH 7.5. When the reduction in the stability constant was compared with other cyclic oligosaccharides (Cys; 119.2 M−1, CD; 14.48 M−1 and HP-CD; 6.75 M−1), S-Cys (K 1:1 = 5.6 M−1) was shown to have the highest decrease in stability constant. These results suggest that the S-Cys could regulate the efficiency of inclusion complexation at external pH values. NMR studies of complex formation between NAP and Cys also showed a different correlation pattern at pH 3.4 and 7.5. This difference in correlation demonstrates that the inclusion complexes between Cys and NAP formed as a result of the differential charge distribution of the carboxyl groups of NAP. The pH-dependent inclusion behavior of Cys for NAP was also evaluated using molecular docking simulations.

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Abbreviations

Cys:

Cyclosophoraoses

S-Cys:

Succinlyated cyclsophoraoses

NAP:

Naproxen

CD:

β-Cyclodextrin

HP-CD:

Hydroxypropyl-β-cyclodextrin

MALDI-TOF:

Matrix assisted laser desorption/ionization-time of flight

NMR:

Nuclear magnetic resonance

DSC:

Differential scanning calorimetry

ROESY:

Rotating frame nuclear overhauser effect spectroscopy

DP:

Degree of polymerization

TLC:

Thin layer chromatography

DS:

Degree of substitution

Deuterium oxide:

D2O

Deuterium methanol:

CD3OD

DEAE:

Diethylaminoethyl

FID:

Free induction decay

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Acknowledgments

This work was supported by the National Research Foundation of Korea Grant funded by the Korean Government (NRF-2011-0026022) and by Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2009-0093824). SDG.

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Authors and Affiliations

  1. Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center & Center for Biotechnology Research in UBITA, Konkuk University, 1 Hwayang-dong Gwangjin-gu, Seoul, 143-701, South Korea

    Chanho Kwon, Daham Jeong, Jun Gull Kim, Jae Min Choi & Seunho Jung

  2. BioChip Research Center, Hoseo University, Asan, 336-795, Republic of Korea

    Youngjin Choi

  3. Department of Applied Chemistry, Dongduk Women’s University, Seoul, 136-714, South Korea

    Sohyun Chun & Seyeon Park

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  1. Chanho Kwon
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  2. Youngjin Choi
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  3. Daham Jeong
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Correspondence to Seunho Jung.

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Kwon, C., Choi, Y., Jeong, D. et al. Inclusion complexation of naproxen with cyclosophoraoses and succinylated cyclosophoraoses in different pH environments. J Incl Phenom Macrocycl Chem 74, 325–333 (2012). https://doi.org/10.1007/s10847-012-0119-7

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  • DOI: https://doi.org/10.1007/s10847-012-0119-7

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