Self-Assembly and Wound Healing Activity of Biomimetic Cycloalkane-Based Lipopeptides
Anindyasundar AdakValeria CastellettoIan W. HamleyJani SeitsonenAniket JanaSatyajit GhoshNabanita MukherjeeSurajit Ghosh
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The self-assembly of lipopeptide (peptide amphiphile) molecules bearing single linear lipid chains has been widely studied, as has their diverse range of bioactivities. Here, we introduce lipopeptides bearing one or two cycloalkane chains (cycloheptadecyl or cyclododecyl) conjugated to the collagen-stimulating pentapeptide KTTKS used in Matrixyl formulations. The self-assembly of all four molecules is probed using fluorescence probe measurements to detect the critical aggregation concentration (CAC), and cryogenic-TEM and small-angle X-ray scattering (SAXS) to image the nanostructure. The peptide conformation is studied using circular dichroism (CD) and FTIR spectroscopies. All the cycloalkane lipopeptides show excellent compatibility with dermal fibroblasts. The compounds bearing one or two cyclododecyl chains (denoted as DKT and DDKT, respectively) show wound healing in diabetic rats, the improvement being markedly enhanced for DDKT. Interestingly, the revival of hair follicles and blood vessels in the dermis were observed, which are the critical markers of effective wound repair. Analysis of H&E-stained tissue images (from a rat model) shows that the rat groups treated with DDKT and DKT displayed a significantly increased amount of regenerated hair follicles, indicating a faster healing process for DDKT compared to the control group. Collagen deposition was also enhanced, especially for DDKT, and by day 20, the DDKT-treated groups had developed a dense collagen network accompanied by a regenerated epidermis. At the same time, the number of blood vessels in DDKT-treated diabetic wounds was significantly higher than in control groups and neovascularization was substantially enhanced, as assayed using α-SMA (a marker for vascular smooth muscle cells) and CD31 (a marker specific to vascular endothelial cells). These results suggest that the lead lipopeptide DDKT exhibits a remarkable pro-vascularization capability and shows great promise for future application as a wound-healing biomaterial.Keywords:
Cycloalkane
Biomimetics
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Liquid phase
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Herein, we have synthesized a variety of cycloalkane-fused arsoles. Cyclopentane and cyclohexane were incorporated into the cycloalkane-fused arsoles. Surprisingly, cyclohexane-fused arsole 2 a gradually decomposed via oxidative ring-opening under ambient conditions, while cyclopentane-fused 1 a was stable. In addition, the Stokes shift of 2 a (7766 cm-1 ) is larger than that of 1 a (5120 cm-1 ). The effects of the fused cycloalkane on the stability and photophysical properties were attributed to the distortion of the cycloalkane. Computational calculations demonstrated that the cyclohexane moiety in 2 a was frustrated upon being incorporated into the rigid arsole ring, while the cyclopentane moiety in 1 a was much less distorted.
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Certain cycloalkane-anellated heterocycles undergo rearrangement under basic or acidic conditions via ring-contraction, ringexpansion or ring-opening pathways to afford new or unusual compounds. The reactivities and properties of cycloalkane-fused heterocycles differ significantly from those of heteroaromatic ring systems. Possible mechanisms are also discussed.
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Biomimicry is an applied science that derives inspiration for solutions to human problems through the study of natural designs, processes and systems. The widespread and practical application of biomimicry as a design method remains unrealized; interior architecture commonly use biology as a library of shapes, but this alone is not biomimetics; it has to have some biology in it. This paper reviews key points and case studies of applications of biomimicry in interior architecture. A critique of the applications shows that biomimetics is the way to innovation and sustainability and interior architecture must move beyond the formalistic characteristics of nature.
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Abstract Spiro[cycloalkane‐1,3′‐[3 H ]indoles] 2 can be obtained from the cycloalkanecarbaldehydes 1 by the Fischer reaction of their phenylhydrazones. These cyclizations are sensitive to the acid catalyst, solvent and temperature employed. Rearrangement of the 2 to the homologous cycloalkane derivatives 3 can occur by an acid catalyst or by thermal treatment of 2 in ethyleneglycol.
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In this work we report the excess molar volumes, [Formula: see text] for the miscible mixtures {xc-C 5 H 10 + (1 − x)CH 3 OH} and {xc-C k H 2k + (1 − x)C l H 2l+1 OH} where k = 5, 6, 7, 8, or 10 and l = 2 or 3. The [Formula: see text] results are discussed in terms of the size of the cycloalkane ring and the type of alcohol. Key words: Excess volumes, cycloalkane + alkanol.
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Technical Biology and Biomimetics.- Buildings, Architecture and Biomimetics.- Biomimetics for Buildings.- Natural Functions and Processes as Prototypes for Buildings.- Biological Support and Envelope Structures and their Counterparts in Buildings.- Products and Architecture - Examples of Biomimetics for Buildings.- Brief Information to Biological Structures.- Appendix.
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Abstract Oxidation of the fluorinated compounds (I) and (III) yields the title cycloalkane diols (II) and (IV), resp., which remain unchanged in refluxing KMnO4/Me2CO.
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Alkane
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