pH-Regulated supramolecular chirality of phenylalanine-based hydrogels

Kousar, Ayesha; Liu, Jinying; Mehwish, Nabila; Wang, Feiliang; Dang-i, Auphedeous Yinme; Feng, Chuanqi

doi:10.1016/j.mtchem.2018.11.005

Cited by 25 publications

(19 citation statements)

References 52 publications

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“…Meanwhile, left-handed (M) helical fibers formed in solution above pH 7.0. Reproduced from ref . Copyright 2019, Elsevier Ltd. (d) Varied chiral nanostructure assembled from l -amino acid derivatives (LPF and LPPG) with different metal ions.…”

Section: Regulation Of Chirality In Supramolecular Hydrogelsmentioning

confidence: 99%

Supramolecular Hydrogels with Tunable Chirality for Promising Biomedical Applications

et al. 2020

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Metrics & MoreArticle Recommendations CONSPECTUS: Chirality exits from molecular-level, supramolecular, and nanoscaled helical structures to the macroscopic level in biological life. Among these various levels, as the central structural motifs in living systems (e.g., double helix in DNA, α-helix, β-sheet in proteins), supramolecular helical systems arising from the asymmetrical spatial stacking of molecular units play a crucial role in a wide diversity of biochemical reactions (e.g., gene replication, molecular recognition, ion transport, enzyme catalysis, and so on). However, the importance of supramolecular chirality and its potential biofunctions has not yet been fully explored. Thus, generating chiral assembly to transfer nature's chiral code to artificial biomaterials is expected to be utilized for developing novel functional biomaterials. As one of the most commonly used biomaterials, supramolecular hydrogels have attracted considerable research interest due to their resemblance to the structure and function of the native extracellular matrix (ECM). Therefore, the performance and manipulation of chiral assembled nanoarchitectures in supramolecular hydrogels may provide useful insights into understanding the role of supramolecular chirality in biology.In this Account, recent progress on chiral supramolecular hydrogels is presented, including how to construct and regulate assembled chiral nanostructures in hydrogels with controllable handedness and then use them to develop chiral hydrogels that could be applied in biology, biochemistry, and medicine. First, a brief introduction is provided to present the basic concept related to supramolecular chirality and the importance of supramolecular chirality in living systems. The chiral assemblies in supramolecular hydrogels are strongly driven by noncovalent interactions between molecular building blocks (such as hydrogen bonding, π−π stacking, hydrophobic, and van der Waals interactions). Consequently, the handedness of these chiral assemblies can be regulated by many extra stimuli including solvents, temperature, pH, metal ions, enzymes, and photoirradiation, which is presented in the second section. This manipulation of the chirality of nanoarchitectures in supramolecular hydrogels can result in the development of potential biofunctions. For example, specific supramolecular chirality-induced biological phenomena (such as controlled cell adhesion, proliferation, differentiation, apoptosis, protein adsorption, drug delivery, and antibacterial adhesion) are presented in detail in the third section. Finally, the outlook of open challenges and future developments of this rapidly evolving field is provided. This account that highlights the diverse chirality-dependent biological phenomena not only helps us to understand the importance of chirality in life but also provides new ideas for designing and preparing chiral materials for more bioapplications.

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Section: Regulation Of Chirality In Supramolecular Hydrogelsmentioning

confidence: 99%

Supramolecular Hydrogels with Tunable Chirality for Promising Biomedical Applications

et al. 2020

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“…s-PLL-b-PPhe exhibited lower CGC than s-PLL-b-PVal and s-PLL-b-PLeu, revealing that the PPhe segment exhibited better hydrogelation ability than the other two segments. It could be attributed that the PPhe segment exhibited additional π-π interactions between benzyl groups and cation-π interactions between PLL and PPhe segments [30,31,36,37].…”

Section: Hydrogelation Of Block Polypeptidesmentioning

confidence: 99%

Polypeptide Composition and Topology Affect Hydrogelation of Star-Shaped Poly(L-lysine)-Based Amphiphilic Copolypeptides

Phan

Huang

Tsai

et al. 2021

Gels

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In this research, we studied the effect of polypeptide composition and topology on the hydrogelation of star-shaped block copolypeptides based on hydrophilic, coil poly(L-lysine)20 (s-PLL20) tethered with a hydrophobic, sheet-like polypeptide segment, which is poly(L-phenylalanine) (PPhe), poly(L-leucine) (PLeu), poly(L-valine) (PVal) or poly(L-alanine) (PAla) with a degree of polymerization (DP) about 5. We found that the PPhe, PLeu, and PVal segments are good hydrogelators to promote hydrogelation. The hydrogelation and hydrogel mechanical properties depend on the arm number and hydrophobic polypeptide segment, which are dictated by the amphiphilic balance between polypeptide blocks and the hydrophobic interactions/hydrogen bonding exerted by the hydrophobic polypeptide segment. The star-shaped topology could facilitate their hydrogelation due to the branching chains serving as multiple interacting depots between hydrophobic polypeptide segments. The 6-armed diblock copolypeptides have better hydrogelation ability than 3-armed ones and s-PLL-b-PPhe exhibits better hydrogelation ability than s-PLL-b-PVal and s-PLL-b-PLeu due to the additional cation–π and π–π interactions. This study highlights that polypeptide composition and topology could be additional parameters to manipulate polypeptide hydrogelation.

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“…Chirality is a fundamental property of life and can occur inherently in individual molecules (e.g., sugars, amino acids) as well as in asymmetric assemblies of molecules (supramolecular chirality). The importance of chirality is seen from the drastically contrasting physiological effects of different drug enantiomers, and hence controlling the enantioselectivity of their synthesis has received extensive research attention. , How molecules interact asymmetrically to form chiral supramolecular superstructures remains to be fully understood, as a multitude of factors including solvent, pH, temperature, and chemical additives can greatly influence the highly complex self-assembly process. For instance, the helical handedness of nanostructures formed from an enantiomerically pure phenylalanine derivative can be completely switched by using different achiral bis(pyridinyl) derivatives .…”

Section: Hydrogel Molecular Sensors and Biosensorsmentioning

confidence: 99%

Bottom-Up Engineering of Responsive Hydrogel Materials for Molecular Detection and Biosensing

Lim

Goh

Loh

2020

ACS Materials Lett.

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Molecular sensors respond to target molecules in their surroundings to detect and sometimes even quantify their concentrations. Traditionally comprised of small organic molecules or metal complexes, these technologies have been essential to biomedical and environmental monitoring, ensuring human health, safety, and general well-being. In the past two decades, analyte-responsive hydrogels have been an emerging technology receiving vast research attention worldwide. Hydrogels capable of detecting a vast array of analytes, including inorganic ions, carbohydrates, thiols, gases, biomolecules (nucleic acids and proteins), and even microorganisms such as bacteria and viruses, have been developed. With the added advantages of bottom-up design at the molecular level and biocompatibility, molecular detection using hydrogel sensors is typically simple to perform, and hydrogels can be integrated with electronic devices to enhance detection sensitivity, or with biomedical devices for in vitro and in vivo studies. Herein, we discuss a range of innovative strategies that have been developed for engineering hydrogel molecular sensors, with emphasis on "bottom-up" molecular engineering to achieve analyte selectivity and sensitivity.

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pH-Regulated supramolecular chirality of phenylalanine-based hydrogels

Cited by 25 publications

References 52 publications

Supramolecular Hydrogels with Tunable Chirality for Promising Biomedical Applications

Supramolecular Hydrogels with Tunable Chirality for Promising Biomedical Applications

Polypeptide Composition and Topology Affect Hydrogelation of Star-Shaped Poly(L-lysine)-Based Amphiphilic Copolypeptides

Bottom-Up Engineering of Responsive Hydrogel Materials for Molecular Detection and Biosensing

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