Design, synthesis, and characterisation of glyoxylamide-based short peptides as self-assembled gels

The synthesis and supramolecular properties of novel glyoxylamide-based short peptides formed via the ring-opening reaction of N-acetylisatins in solution phase are described. The short peptides self-assembled into gels, which were examined for their mechanical and morphological characteristics usin...

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Bibliographic Details
Published inNew journal of chemistry Vol. 41; no. 22; pp. 13462 - 13471
Main Authors Aldilla, Vina R., Nizalapur, Shashidhar, Martin, Adam, Marjo, Chris E., Rich, Anne, Yee, Eugene, Suwannakot, Panthipa, Black, David StC, Thordarson, Pall, Kumar, Naresh
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
PHYSICAL-PROPERTIES
HYDROGELS
PEPTIDOMIMETICS
GELATORS
POTENTIAL APPLICATION
N-ACYLISATINS
NANOTUBES
AMPHIPHILES
TECHNOLOGICAL APPLICATIONS
DIPEPTIDE
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Summary:The synthesis and supramolecular properties of novel glyoxylamide-based short peptides formed via the ring-opening reaction of N-acetylisatins in solution phase are described. The short peptides self-assembled into gels, which were examined for their mechanical and morphological characteristics using multiple spectroscopic and microscopy techniques. The critical gel concentration and mechanical strength of the self-assembled gels were influenced by the presence of electronegative substituents (such as fluoro, in 5b) or hydrophobic substituents (such as bromo, 5d) respectively in the short peptides. Moreover, in vitro cytotoxicity assays demonstrated that these compounds were non-toxic to mammalian cells.
ISSN:1144-0546
1369-9261
DOI:10.1039/c7nj02248d