Topical compositions and methods utilizing peptides containing lipid-modified cysteine-containing peptides
A topical composition, cysteine technology, applied in the direction of peptide preparation methods, chemical instruments and methods, drug combinations, etc., can solve skin damage and other problems
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[0151] As described in the Examples below, in certain exemplary embodiments, peptides and formulations of the peptides are prepared according to the following general procedures. It should be appreciated that while the general methods describe the synthesis of certain peptides and formulations of the invention, the following general methods and others known to those of ordinary skill in the art can be applied to each of the peptides and formulations disclosed herein By.
example 1
[0153] Method for preparing lipidated peptides
[0154] Protein extracts (100 mL, 5 mg / ml) were mixed with trypsin (100 mL, 0.1 mg / ml) or other endopeptidases (0.1 mg / ml) and incubated at 37°C for 2 hours. The extract was further digested by exopeptidase (100 mL, 0.1 mg / ml). After digestion, the free amino groups of the hydrolyzed protein (about 4.6 mmol) were stirred with acetic anhydride (10 mL) in buffer solution overnight at room temperature. The protected peptide was converted to 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (1.79 g, 4.6 millimoles) of the activated ester. The active peptide was reacted with lipidated cysteine residues (such as farnesyl-S-cysteine, phytyl- S-cysteine, or geranylgeranyl-S-cysteine) (4.6 mmol) was coupled overnight, yielding 1.0 g to 1.8 g of the desired mixture of homogeneously lipid-modified peptides .
example 2
[0156] Method for preparing lipidated peptides
[0157] Protein extracts (100 mL, 5 mg / ml) were mixed with trypsin (100 mL, 0.1 mg / ml) or other endopeptidases (0.1 mg / ml) and incubated at 37°C for 2 hours. The resulting hydrolyzed peptide mixture was treated with DTT (770 mg, 4.6 mmol) overnight at room temperature to reduce the disulfide bonds. Methods such as reaction with Ellman's reagent (DTNB, 5,5'-dithiobis-(2-nitrobenzoic acid)) are used to measure the free thiol content in a sample of material. A sample (1 ml) of the hydrolyzed protein extract was dissolved in 0.1 M potassium phosphate buffer (pH 7.4) and mixed with 20 mM DTNB solution (50 μL) in the same buffer. Absorbance was observed at 412 nm and 30°C. DTNB reagent reacts with free thiols to release 2-nitro-5-thiobenzoic acid (TNB) (1 equiv), which has a molar extinction coefficient of 14,150 M at 30 °C -1 cm -1 (The concentration of TNB is equal to the concentration of thiol groups in the protein sample). The...
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