6533b82afe1ef96bd128b9e7

RESEARCH PRODUCT

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

Uladzimir BildziukevichElina SievänenDavid ŠAmanZdeněk WimmerZdeněk WimmerErkki KolehmainenMiroslav ŠLoufEva Kaletová

subject

Magnetic Resonance SpectroscopyScanning electron microscopeClinical BiochemistrySupramolecular chemistrymacromolecular substancesDOSY-NMRMicroscopy Atomic Force010402 general chemistry01 natural sciencesBiochemistryAbsorbancechemistry.chemical_compoundEndocrinologyMicroscopy Electron TransmissionBathochromic shiftBetulinic AcidAcetonitrileta116Molecular BiologyPharmacologyAqueous solutionMolecular Structure010405 organic chemistryChemistryOrganic Chemistryta1182technology industry and agricultureAmidesTriterpenes0104 chemical sciencesCrystallographyTransmission electron microscopySEMTEMSpermineMicroscopy Electrochemical ScanningAFMPentacyclic TriterpenesChirality (chemistry)

description

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.

yearjournalcountryeditionlanguage
2016-06-02Steroids
https://doi.org/10.1016/j.steroids.2016.07.007