Light-triggered syneresis of a water insoluble peptide-hydrogel effectively removes small molecule waste contaminants

Pramanik, Bapan; Chowdhuri, Sumit; Scherman, Oren A.; Das, Debapratim

doi:10.1039/c9cc09225k

Cited by 31 publications

(40 citation statements)

References 29 publications

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“…Compounds 1 and 4 displayed syneresis, as already reported for 1 . 27 , 28 This feature, which consists of the gel contraction with concomitant release of liquid, may be attractive for the capture and release of small molecules, 38 , 39 such as pollutants or drugs, provided that release kinetics are controlled. Compounds 2 , 3 , and 6 yielded stable and homogeneous hydrogels; in particular, compounds 2 and 3 formed materials of high transparency, which is a desirable feature for optical applications.…”

Section: Resultsmentioning

confidence: 99%

Heterochirality and Halogenation Control Phe-Phe Hierarchical Assembly

et al. 2020

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Diphenylalanine is an amyloidogenic building block that can form a versatile array of supramolecular materials. Its shortcomings, however, include the uncontrolled hierarchical assembly into microtubes of heterogeneous size distribution and well-known cytotoxicity. This study rationalized heterochirality as a successful strategy to address both of these pitfalls and it provided an unprotected heterochiral dipeptide that self-organized into a homogeneous and optically clear hydrogel with excellent ability to sustain fibroblast cell proliferation and viability. Substitution of one l -amino acid with its d -enantiomer preserved the ability of the dipeptide to self-organize into nanotubes, as shown by single-crystal XRD analysis, whereby the pattern of electrostatic and hydrogen bonding interactions of the backbone was unaltered. The effect of heterochirality was manifested in subtle changes in the positioning of the aromatic side chains, which resulted in weaker intermolecular interactions between nanotubes. As a result, d -Phe- l -Phe self-organized into homogeneous nanofibrils with a diameter of 4 nm, corresponding to two layers of peptides around a water channel, and yielded a transparent hydrogel. In contrast with homochiral Phe-Phe stereoisomer, it formed stable hydrogels thermoreversibly. d -Phe- l -Phe displayed no amyloid toxicity in cell cultures with fibroblast cells proliferating in high numbers and viability on this biomaterial, marking it as a preferred substrate over tissue-culture plastic. Halogenation also enabled the tailoring of d -Phe- l -Phe self-organization. Fluorination allowed analogous supramolecular packing as confirmed by XRD, thus nanotube formation, and gave intermediate levels of bundling. In contrast, iodination was the most effective strategy to augment the stability of the resulting hydrogel, although at the expense of optical transparency and biocompatibility. Interestingly, iodine presence hindered the supramolecular packing into nanotubes, resulting instead into amphipathic layers of stacked peptides without the occurrence of halogen bonding. By unravelling fine details to control these materials at the meso- and macro-scale, this study significantly advanced our understanding of these systems.

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Section: Resultsmentioning

confidence: 99%

Heterochirality and Halogenation Control Phe-Phe Hierarchical Assembly

et al. 2020

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“…Shrinkage, or syneresis, of supramolecular gels is unusual. [45][46][47] Normally, such syneresis is limited to cross-linked polymer gels. Here, the syneresis can be ascribed to the pH induced change in molecular packing (as observed from UV-vis and uorescence) that allows the molecules to stack effectively (Fig.…”

Section: Resultsmentioning

confidence: 99%

Controlling hydrogel properties by tuning non-covalent interactions in a charge complementary multicomponent system

2021

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“…Das et al, investigated a hydrogelator containing azobenzenyl and cysteine-based peptide units, Azo-KC ( Figure 21 a), whose gels in water with small amounts of NaOH undergo synereses due to trans -to -cis isomerization of the azo group when irradiated in the UV region [ 85 ]. Thus, the Azo-KC hydrogel (H-gel) shrinks up to 50% of its original volume (shrunken gel, S-gel) by expelling excess water when irradiated in the UV region.…”

Section: Properties Of Luminescent Gelsmentioning

confidence: 99%

“…All measurements were carried out at room temperature. Republished from [ 85 ] with permission of The Royal Society of Chemistry.…”

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Luminescent Behavior of Gels and Sols Comprised of Molecular Gelators

Grover

Weiss

2021

Gels

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Light-triggered syneresis of a water insoluble peptide-hydrogel effectively removes small molecule waste contaminants

Abstract: A water insoluble hydrogel that expels 50% of the water upon irradiation with UV-light.

Cited by 31 publications

References 29 publications

Heterochirality and Halogenation Control Phe-Phe Hierarchical Assembly

Heterochirality and Halogenation Control Phe-Phe Hierarchical Assembly

Controlling hydrogel properties by tuning non-covalent interactions in a charge complementary multicomponent system

Luminescent Behavior of Gels and Sols Comprised of Molecular Gelators

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