Aging-Induced Structural Transition of Nanoscale Oleanolic Acid Amphiphiles and Selectivity against Gram-Positive Bacteria
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F22%3A00557299" target="_blank" >RIV/61389030:_____/22:00557299 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/22:00557299 RIV/60461373:22330/22:43924748 RIV/61989592:15110/22:73612649
Result on the web
<a href="http://doi.org/10.1021/acsanm.1c04374" target="_blank" >http://doi.org/10.1021/acsanm.1c04374</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acsanm.1c04374" target="_blank" >10.1021/acsanm.1c04374</a>
Alternative languages
Result language
angličtina
Original language name
Aging-Induced Structural Transition of Nanoscale Oleanolic Acid Amphiphiles and Selectivity against Gram-Positive Bacteria
Original language description
Triterpenoids are among the largest groups of functional plant secondary metabolites but with intrinsically low water solubility. Because of their rigid backbone, multiple chiral centers, and functional groups, they are suitable for synthesizing water-soluble and conformationally rigid triterpenoid amphiphiles with unique self-assembly behavior. In this context, we present the aqueous self-assembly, structural transition, and antimicrobial properties of nanoscale oleanolic acid-spermine conjugates (2-4). The conjugates contain either one or two spermine moieties connected through a 1,4-disubstituted 1,2,3-triazole linker. We use cryogenic transmission electron microscopy (cryo-TEM) imaging to show that conjugates 2 and 3 self-assemble in water initially into kinetically favored metastable micellar nanoparticles (d ≈ 6-10 nm). The nanoparticles further reorganize to form thermodynamically stable helical nanofibers. Notably, cryo-TEM imaging also suggests the formation of spherulite-like structures. Time-dependent infrared (IR) spectroscopy reveals the role of hydration and dehydration in the structural transition of initial micelle-like structures into thermodynamically stable nanofibers. Electronic and vibrational circular dichroism (ECD and VCD, respectively) spectroscopy in the solution state suggests the formation of chiral superstructures with a left-handed helical twist. The conjugates display antibacterial properties with high selectivity against Gram-positive bacterial strains. The results help us understand fibrillar network formation in supramolecular gels, and demonstrate that the position and number of spermine groups influence the self-assembly behavior of the conjugates in aqueous media and their biological properties.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ACS Applied Nano Materials
ISSN
2574-0970
e-ISSN
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Volume of the periodical
5
Issue of the periodical within the volume
3
Country of publishing house
US - UNITED STATES
Number of pages
12
Pages from-to
3799-3810
UT code for WoS article
000800286500068
EID of the result in the Scopus database
2-s2.0-85125638636