NDLI: Nanodimer cyclodextrin ligands with high affinity to steroids

Content Provider	Springer Nature Link
Author	Khomutov, Sergey Dova, Marina V.
Copyright Year	2010
Abstract	Molecular-imprinting by cross-linking of ligands of β-cyclodextrin (CD) complex with steroids has been developed for the synthesis of tailor-made CD dimer. Steroids of androstane (9α-hydroxy-androst-4-en-3,17-dione, androst-4-en-3,17-dione, androsta-1,4-dien-3,17-dione (ADD)) and pregnane (hydrocortisone, 6-methyl-hydrocortisone, 20-hydroxymethylpregna-1,4-diene-3-one (HMPD)) series were used as template molecules. For imprinting procedure, crystalline β-CD complexes of exact stoichiometry (β-CD:steroid template = 2:1) were synthesized following by toluene 2,4-diisocyanate (TDI) cross-linking. The attempts to produce CD dimer for steroid without hydrophobic side chain failed, while tailor-made CD dimer has been obtained using HMPD as a template. The dimer was characterized by $^{1}$H NMR and mass-spectrometry. The complex stability constant (K$_{S}$) towards HMPD template exceeded 10$^{7}$ M$^{−1}$. The K$_{S}$ of CD dimer with ADD exceeded the corresponded value of TDI-modified CD monomer by more than an order of magnitude. The dimer was applied for quantitative extraction of ADD from aqueous solution using dialysis membranes impermeable for CD. The value of K$_{S}$ for ADD estimated from balanced concentrations of dialysis data corresponded to that calculated by nonlinear spectrometric method.
Starting Page	353
Ending Page	357
Page Count	5
File Format	PDF
ISSN	09230750
Journal	Journal of Inclusion Phenomena and Macrocyclic Chemistry
Volume Number	70
Issue Number	3-4
e-ISSN	15731111
Language	English
Publisher	Springer Netherlands
Publisher Date	2010-11-12
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Cyclodextrin Steroid Dimer Complex stability constant Food Science Organic Chemistry Crystallography
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics Food Science

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