Micelle and Nanotape Formation of Benzene Tricarboxamide Analogues with Selective Cancer Cell Cytotoxicity

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Abstract

Analogues of benzene-1,3,5-tricarboxamide bearing combinations of different alkyl chains (dodecyl to octadecyl) and ester-linked PEG (polyethylene glycol) chains are shown to self-assemble into either micelles or nanotapes in aqueous solution, depending on the architecture (number of alkyl vs PEG chains). The cytotoxicity to cells is selectively greater for breast cancer cells than fibroblast controls in a dose-dependent manner. The compounds show strong stability, retaining their self-assembled structures at low pH (relevant to acidic tumor conditions) and in buffer and cell culture media.

Original languageEnglish
Pages (from-to)46843-46848
Number of pages6
JournalACS Omega
Volume7
Issue number50
DOIs
Publication statusPublished - 20 Dec 2022
MoE publication typeA1 Journal article-refereed

Funding

N.A. acknowledges support from the Saudi Arabian Cultural Bureau. I.W.H. thanks EPSRC for the award of an Established Career Fellowship (ref EP/V053396/1). We thank Diamond Light Source for the award of beamtime (ref sm28659-1 and -2) and Barbara Gerbelli (FAPESP-funded visiting postdoc at University of Reading), Nathan Cowieson (Diamond), and Katsuaki Inoue (Diamond) for assistance with the SAXS measurements. We are grateful to Az Alddien Natfji (University of Reading) for help with cell assays.

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