A New Way to Silicone‐Based Peptide Polymers

Jebors, Said; Ciccione, Jeremie; Al‐Halifa, Soultan; Nottelet, Benjamin; Enjalbal, Christine; M’Kadmi, Céline; Amblard, Muriel; Mehdi, Ahmad; Martinez, Jean; Subra, Gilles

doi:10.1002/ange.201411065

Cited by 5 publications

(6 citation statements)

References 33 publications

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“…Ghrelin usually activates all signalling pathways. On the other hand, signalling of synthetic ligands may be selective or functionally biased . Some antagonists are able to antagonise food intake but not the secretion of GH .…”

Section: Discussionmentioning

confidence: 99%

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Peptide mimetic of N‐terminal ghrelin enhances ghrelin‐induced growth hormone secretion and c‐Fos expression in mice

Lunder

Vodnik

Kubale

et al. 2018

J Neuroendocrinology

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Orexigenic peptide ghrelin and its receptor have been extensively investigated as potential therapeutic targets, primarily because of their role in feeding initiation and growth hormone (GH) release. However, no specific ghrelin targeting anti‐obesity or cachexia therapeutics are available for clinical use thus far and further efforts in this direction are warranted. The present study aimed to find new peptide drug leads modulating ghrelin signal transduction. By targeting neutralising antibodies against ghrelin with phage display libraries, we aimed to identify peptides binding to the cognate receptor. Four synthetic peptides were selected and tested using calcium screening assays. The most effective competitive antagonist FSFLPPE was further tested in vivo. Administration of the peptide produced no significant effect on either food intake or GH release. Surprisingly, when co‐administered with ghrelin, the peptide significantly enhanced GH secretion and c‐Fos expression. The evidence obtained in the present study indicates that FSFLPPE might act as an ago‐allosteric modulator.

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Section: Discussionmentioning

confidence: 99%

“…On the other hand, signalling of synthetic ligands may be selective 36 or functionally biased. 35,37 Some antagonists are able to antagonise food intake but not the secretion of GH. 38 Other antagonists, such as GSK161443, decrease GH secretion in vivo but increase food intake and weight gain either after single or multiple administration.…”

Section: Discussionmentioning

confidence: 99%

Peptide mimetic of N‐terminal ghrelin enhances ghrelin‐induced growth hormone secretion and c‐Fos expression in mice

Lunder

Vodnik

Kubale

et al. 2018

J Neuroendocrinology

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“…We recently reported on a strategy yielding siloxane polymers of well‐defined peptide sequences starting from hybrid dimethylhydroxysilane‐derivatized peptides . In contrast to linear peptide polymers, which were obtained via N‐terminal and C‐terminal modifications, comb‐peptide polymers were synthesized by addition of a lysine residue at the N‐terminus, which was derivatized at its α and ε primary amino groups by isocyanopropyl dimethylchlorosilane.…”

Section: Introductionmentioning

confidence: 99%

“…Comb‐polymers from peptide sequences. (A) using N‐terminally modified lysine with dimethyl hydroxysilyl groups . (B) New strategy involving methyldihydroxysilyl N‐terminal peptides.…”

Section: Introductionmentioning

confidence: 99%

Turning peptides in comb silicone polymers

Jebors

Pinese

Nottelet

et al. 2015

Journal of Peptide Science

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We have recently reported on a new class of silicone-peptide' biopolymers obtained by polymerization of di-functionalized chlorodimethylsilyl hybrid peptides. Herein, we describe a related strategy based on dichloromethylsilane-derived peptides, which yield novel polymers with a polysiloxane backbone, comparable with a silicone-bearing pendent peptide chains. Interestingly, polymerization is chemoselective toward amino acids side-chains and proceeds in a single step in very mild conditions (neutral pH, water, and room temperature). As potential application, a cationic sequence was polymerized and used for antibacterial coating.

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“…ICPCDMS was already used to prepare silicone-based peptide polymers. 28 The unprotected peptide H-GRGDSP-OH was first prepared by Fmoc/tBu solid phase peptide synthesis and functionalized with a triethoxysilyl group using ICPTES to yield 2 (Scheme 1). A 10 wt % solution of the hybrid PEG 1 containing 0.3 wt % of NaF was prepared and the hybrid block 2 was added to this solution at a concentration of 10 mol % or 20 mol % regarding hybrid block 1 (i.e., at 4.0 mM or 8.0 mM).…”

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confidence: 99%

Easy Synthesis of Tunable Hybrid Bioactive Hydrogels

et al. 2016

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Material and Method2-Chorotrityl chloride resin (100-200 Mesh, 1.44 mmol Cl/g resin) and Fmoc-Rink Amide AM PS resin (100-200 Mesh, 0.94 mmol/g resin) were purchased from Iris Biotech and stored at 4°C. Protected amino acids and HBTU were purchased from Iris Biotech, Senn Chemicals and Bachem. PEG (MW = 2000 g/mol) was purchased from Alfa Aesar. All reagents and solvents were from Alfa Aesar, Acros, Sigma-Aldrich or Merck and were used without further purification. Water sensitive reactions were carried out under an argon atmosphere with anhydrous solvents. Preparative chromatographic purification was performed using Waters HPLC 4000 instrument, equipped with a UV detector 486 and Waters Delta-Pack 40×100 mm, 100Å, 15 µm, C 18 reversed-phase column using a flow rate of 50 mL/min. Solvents employed were water/0.1% TFA and ACN/0.1% TFA. Samples for LC/MS analyses were prepared in acetonitrile/water (50:50, v/v) mixture, containing 0.1% TFA. The LC/MS system consisted of a Waters Alliance 2695 HPLC, coupled to a Water Micromass ZQ spectrometer (electrospray ionization mode, ESI+). All the analyses were carried out using a Phenomenex Onyx, 25 x 4.6 mm reversed-phase column. A flow rate of 3 mL/min and a gradient of (0-100)% B over 2.5 min were used. Eluent A: water/0.1% HCO 2 H; eluent B: acetonitrile/0.1% HCO 2 H. UV detection was performed at 214 nm. Electrospray mass spectra were acquired at a solvent flow rate of 200 µL/min. Nitrogen was used for both the nebulizing and drying gas. The data were obtained in a scan mode ranging from 100 to 1000 m/z or 250 to 1500 m/z to in 0.7 sec intervals. High Resolution Mass Spectrometric analyses were performed with a time of flight (TOF) mass spectrometer fitted with an Electrospray Ionisation source. All measurements were performed in the positive ion mode. 1 H, 13 C and 29 Si NMR spectra were recorded at room temperature in deuterated solvents on a Bruker AMX/400 spectrometer operating at 400, 101 and 79 MHz respectively. Chemical shifts (δ) are reported in parts per million using residual non-deuterated solvents as internal references (CHCl 3 in CDCl 3 , δH = 7.26 ppm; DMSO-d6, δH = 2.50 ppm). Signals are indicated as s (singlet), d (doublet), t (triplet), q (quartet), dt (double triplet), m (multiplet), br (broad)… Coupling constants are measured in Hertz.Picture of the experimental set-up for antibacterial assays. Upside-down Petri dish containing from top to bottom: hybrid PEG hydrogel, MTT stained bacteria, nitrocellulose membrane, tryptic soy agar culture medium.

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A New Way to Silicone‐Based Peptide Polymers

Cited by 5 publications

References 33 publications

Peptide mimetic of N‐terminal ghrelin enhances ghrelin‐induced growth hormone secretion and c‐Fos expression in mice

Peptide mimetic of N‐terminal ghrelin enhances ghrelin‐induced growth hormone secretion and c‐Fos expression in mice

Turning peptides in comb silicone polymers

Easy Synthesis of Tunable Hybrid Bioactive Hydrogels

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