Spectral and microscopic study of self-assembly of novel cationic spermine amides of betulinic acid

[Display omitted] •Supramolecular characteristics studied by the UV–VIS-NIR and DOSY-NMR spectra.•Fibrous self-assembly observed by the AFM, SEM and TEM micrographs.•Bathochromic shifts in the UV–VIS-NIR spectra indicates fibrous J-type aggregates.•DOSY-NMR showed non-linear dependence and results i...

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Bibliographic Details
Published in:Steroids 2017-01, Vol.117, p.90-96
Main Authors: Bildziukevich, Uladzimir, Kaletová, Eva, Šaman, David, Sievänen, Elina, Kolehmainen, Erkki T., Šlouf, Miroslav, Wimmer, Zdeněk
Format: Article
Language:English
Subjects:
AFM
Amides - chemistry
Betulinic acid
DOSY-NMR
Magnetic Resonance Spectroscopy
Microscopy, Atomic Force
Microscopy, Electrochemical, Scanning
Microscopy, Electron, Transmission
Molecular Structure
SEM
Spermine
Spermine - chemistry
TEM
Triterpenes - chemistry
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Summary:[Display omitted] •Supramolecular characteristics studied by the UV–VIS-NIR and DOSY-NMR spectra.•Fibrous self-assembly observed by the AFM, SEM and TEM micrographs.•Bathochromic shifts in the UV–VIS-NIR spectra indicates fibrous J-type aggregates.•DOSY-NMR showed non-linear dependence and results in a self-assembly behavior. Supramolecular characteristics of two spermine amides of betulinic acid (1 and 2) were studied by measuring and evaluating their UV–VIS-NIR spectra in aqueous acetonitrile and DOSY-NMR spectra in tetradeuteromethanol, accompanied by atomic force microscopy (AFM) images, scanning electron microscopy (SEM) micrographs, and transmission electron microscopy (TEM) micrographs. Fibrous supramolecular self-assembly of 1 and 2 was observed by AFM images, as well as by the SEM and TEM micrographs. Bathochromic shifts of the absorbance maximum at 870nm to 1015–970nm in the UV–VIS-NIR spectra were observed with increasing water content in the acetonitrile/water systems, indicating formation of fibrous J-type aggregates. Variable temperature DOSY-NMR spectral measurement showed non-linear dependence that also suggests self-assembly behavior of the studied systems. Chiral supramolecular structures were formed by self-assembling due to the chirality of the monomeric molecules. Application of aqueous media during self-assembly procedures is an important factor in the development of targeted drug delivery systems.
ISSN:0039-128X
1878-5867
DOI:10.1016/j.steroids.2016.07.007