|
|
|
|
| LEADER |
01000caa a22002652c 4500 |
| 001 |
NLM374052573 |
| 003 |
DE-627 |
| 005 |
20250306082152.0 |
| 007 |
cr uuu---uuuuu |
| 008 |
240626s2024 xx |||||o 00| ||eng c |
| 024 |
7 |
|
|a 10.1021/acs.langmuir.4c00889
|2 doi
|
| 028 |
5 |
2 |
|a pubmed25n1246.xml
|
| 035 |
|
|
|a (DE-627)NLM374052573
|
| 035 |
|
|
|a (NLM)38917360
|
| 040 |
|
|
|a DE-627
|b ger
|c DE-627
|e rakwb
|
| 041 |
|
|
|a eng
|
| 100 |
1 |
|
|a Khamrui, Rajesh
|e verfasserin
|4 aut
|
| 245 |
1 |
0 |
|a Hydrogen-Bonding-Regulated Morphology Control and the Impact on the Antibacterial Activity of Cationic π-Amphiphiles
|
| 264 |
|
1 |
|c 2024
|
| 336 |
|
|
|a Text
|b txt
|2 rdacontent
|
| 337 |
|
|
|a ƒaComputermedien
|b c
|2 rdamedia
|
| 338 |
|
|
|a ƒa Online-Ressource
|b cr
|2 rdacarrier
|
| 500 |
|
|
|a Date Completed 09.07.2024
|
| 500 |
|
|
|a Date Revised 09.07.2024
|
| 500 |
|
|
|a published: Print-Electronic
|
| 500 |
|
|
|a Citation Status MEDLINE
|
| 520 |
|
|
|a This manuscript describes the synthesis, self-assembly, and antibacterial properties of naphthalene-diimide (NDI)-derived cationic π-amphiphiles. Three such asymmetric NDI derivatives with a nonionic hydrophilic wedge and a guanidine group in the two opposite sides of the NDI chromophore were considered. They differ by a single functional group (hydrazide, amide, and ester for NDI-1, NDI-2, and NDI-3, respectively), located in the linker between the NDI and the hydrophilic wedge. For NDI-1, the H-bonding among the hydrazides regulated unilateral stacking and a preferential direction of curvature of the resulting supramolecular polymer, producing an unsymmetric polymersome with the guanidinium groups displayed at the outer surface. NDI-3, lacking any H-bonding group, exhibits π-stacking without any preferential orientation and generates spherical particles with a relatively poor display of the guanidium groups. In sharp contrast to NDI-1, NDI-2 exhibits an entangled one-dimensional (1D) fibrillar morphology, indicating the prominent role of the H-bonding motif of the amide group and flexibility of the linker. The antibacterial activity of these assemblies was probed against Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative). NDI-1 showed the most promising antibacterial activity with a minimum inhibitory concentration (MIC) of ∼7.8 μg/mL against S. aureus and moderate activity (MIC ∼ 125 μg/mL) against E. coli. In sharp contrast, NDI-3 did not show any significant activity against the bacteria, suggesting a strong impact of the H-bonding-regulated directional assembly. NDI-2, forming a fibrillar network, showed moderate activity against S. aureus and negligible activity against E. coli, highlighting a significant impact of the morphology. All of these three molecules were found to be compatible with mammalian cells from the 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl-tetrazolium bromide (MTT) and hemolysis assay. The mechanistic investigation by membrane polarization assay, live/dead fluorescence assay, and microscopy studies confirmed the membrane disruption mechanism of cell killing for the lead candidate NDI-1
|
| 650 |
|
4 |
|a Journal Article
|
| 650 |
|
7 |
|a Anti-Bacterial Agents
|2 NLM
|
| 650 |
|
7 |
|a Naphthalenes
|2 NLM
|
| 650 |
|
7 |
|a Imides
|2 NLM
|
| 650 |
|
7 |
|a naphthalenediimide
|2 NLM
|
| 650 |
|
7 |
|a 22291-04-9
|2 NLM
|
| 650 |
|
7 |
|a Cations
|2 NLM
|
| 700 |
1 |
|
|a Mukherjee, Arunima
|e verfasserin
|4 aut
|
| 700 |
1 |
|
|a Ghosh, Suhrit
|e verfasserin
|4 aut
|
| 773 |
0 |
8 |
|i Enthalten in
|t Langmuir : the ACS journal of surfaces and colloids
|d 1985
|g 40(2024), 27 vom: 09. Juli, Seite 13870-13878
|w (DE-627)NLM098181009
|x 1520-5827
|7 nnas
|
| 773 |
1 |
8 |
|g volume:40
|g year:2024
|g number:27
|g day:09
|g month:07
|g pages:13870-13878
|
| 856 |
4 |
0 |
|u http://dx.doi.org/10.1021/acs.langmuir.4c00889
|3 Volltext
|
| 912 |
|
|
|a GBV_USEFLAG_A
|
| 912 |
|
|
|a SYSFLAG_A
|
| 912 |
|
|
|a GBV_NLM
|
| 912 |
|
|
|a GBV_ILN_22
|
| 912 |
|
|
|a GBV_ILN_350
|
| 912 |
|
|
|a GBV_ILN_721
|
| 951 |
|
|
|a AR
|
| 952 |
|
|
|d 40
|j 2024
|e 27
|b 09
|c 07
|h 13870-13878
|