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

被引：21

作者：

Bildziukevich, Uladzimir ^{[1
,2
]}

Kaletova, Eva ^{[3
]}

Saman, David ^{[3
]}

Sievanen, Elina ^{[4
]}

Kolehmainen, Erkki T. ^{[4
]}

Slouf, Miroslav ^{[5
]}

Wimmer, Zdenek ^{[1
,2
]}

机构：

[1] Acad Sci Czech Republ, Isotope Lab, Inst Expt Bot, Videnska 1083, Prague 14220 4, Czech Republic

[2] Univ Chem & Technol, Dept Chem Nat Cpds, Tech 5, Prague 16628 6, Czech Republic

[3] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Flemingovo Namesti 2, CR-16610 Prague 6, Czech Republic

[4] Univ Jyvaskyla, Dept Chem, POB 35, FI-40014 Jyvaskyla, Finland

[5] Acad Sci Czech Republ, Inst Macromol Chem, Heyrovsky Sq 2, CR-16206 Prague 6, Czech Republic

来源：

STEROIDS | 2017年 / 117卷

关键词：

Spermine; Betulinic acid; AFM; SEM; TEM; DOSY-NMR; DERIVATIVES; SQUALAMINE; GELATION; CANCER; AGENTS; CELLS;

D O I：

10.1016/j.steroids.2016.07.007

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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. (C) 2016 Elsevier Inc. All rights reserved.

引用

页码：90 / 96

页数：7

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