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

0474554 - ÚEB 2018 RIV US eng J - Journal Article
Bildziukevich, Uladzimir - Kaletová, Eva - Šaman, David - Sievanen, E. - Kolehmainen, E. T. - Šlouf, Miroslav - Wimmer, Zdeněk
Spectral and microscopic study of self-assembly of novel cationic spermine amides of betulinic acid.
Steroids. Roč. 117, JAN (2017), s. 90-96. ISSN 0039-128X. E-ISSN 1878-5867
R&D Projects: GA MŠMT(CZ) LD13057; GA MŠMT LD15012; GA MŠMT(CZ) LO1507
Institutional support: RVO:61389030 ; RVO:61388963 ; RVO:61389013
Keywords : derivatives * squalamine * gelation * cancer * agents * cells * Spermine * Betulinic acid * afm * sem * tem * dosy-NMR
OECD category: Biochemical research methods; Polymer science (UMCH-V); Organic chemistry (UOCHB-X)
Impact factor: 2.523, year: 2017

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 tetra-deuteromethanol, 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 870 nm to 1015-970 nm 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.
Permanent Link: http://hdl.handle.net/11104/0271580