Dataset Information

Dramatically Increased Binding Constant of Water-Soluble Cyclodextrin Hyperbranched Polymers: Explored with Diffusion Ordered NMR Spectroscopy (DOSY).

ABSTRACT: We report that the polymerization of cyclodextrin (CD) with epichlorohydrin (ECH) dramatically increases the binding constant of CD to vanillin, from 55 to 8.4 × 10³ M^-1, by approximately 100 times, as determined by diffusion ordered spectroscopy (DOSY)-¹H NMR. The binding constant increased with an increase of the ECH content of the polymer, although ECH polymers without CDs showed no affinity at all, suggesting that the hydrophobicity of the ECH network outside of CDs helps to enhance the binding. This increased binding constant allows CD-ECH polymers to increase the drug loading ratio, which may be one of the most critical issues for drug delivery systems.

SUBMITTER: Doan ATN

PROVIDER: S-EPMC8991930 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Publications

Dramatically Increased Binding Constant of Water-Soluble Cyclodextrin Hyperbranched Polymers: Explored with Diffusion Ordered NMR Spectroscopy (DOSY).

Doan Anh Thi Ngoc ATN Doan Van Thi Hong VTH Katsuki Jun J Fujii Shota S Kono Hiroyuki H Sakurai Kazuo K

ACS omega 20220325 13

We report that the polymerization of cyclodextrin (CD) with epichlorohydrin (ECH) dramatically increases the binding constant of CD to vanillin, from 55 to 8.4 × 103 M-1, by approximately 100 times, as determined by diffusion ordered spectroscopy (DOSY)-1H NMR. The binding constant increased with an increase of the ECH content of the polymer, although ECH polymers without CDs showed no affinity at all, suggesting that the hydrophobicity of the ECH network outside ...[more]

PMID: 35415377

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Project description:Diffusion-ordered NMR spectroscopy (DOSY) can be used to analyze mixtures of compounds since resonances deriving from different compounds are distinguished by their diffusion coefficients (D). Previously, DOSY has mostly been used for organometallic and polymer analysis, we have now applied DOSY to investigate diffusion coefficients of structurally diverse organic compounds such as natural products (NP). The experimental Ds derived from 55 diverse NPs has allowed us to establish a power law relationship between D and molecular weight (MW) and therefore predict MW from experimental D. We have shown that D is also affected by factors such as hydrogen bonding, molar density and molecular shape of the compound and we have generated new models that incorporate experimentally derived variables for these factors so that more accurate predictions of MW can be calculated from experimental D. The recognition that multiple physicochemical properties affect D has allowed us to generate a polynomial equation based on multiple linear regression analysis of eight calculated physicochemical properties from 63 compounds to accurately correlate predicted D with experimental D for any known organic compound. This equation has been used to calculate predicted D for 217 043 compounds present in a publicly available natural product database (DEREP-NP) and to dereplicate known NPs in a mixture based on matching of experimental D and structural features derived from NMR analysis with predicted D and calculated structural features in the database. These models have been validated by the dereplication of a mixture of two known sesquiterpenes obtained from Tasmannia xerophila and the identification of new alkaloids from the bryozoan Amathia lamourouxi. These new methodologies allow the MW of compounds in mixtures to be predicted without the need for MS analysis, the dereplication of known compounds and identification of new compounds based solely on parameters derived by DOSY NMR.

Dataset Information

Dramatically Increased Binding Constant of Water-Soluble Cyclodextrin Hyperbranched Polymers: Explored with Diffusion Ordered NMR Spectroscopy (DOSY).

Publications

Dramatically Increased Binding Constant of Water-Soluble Cyclodextrin Hyperbranched Polymers: Explored with Diffusion Ordered NMR Spectroscopy (DOSY).

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