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Polypeptide derivatives for generating stable micro-molecular hydrogel

A technology of small molecule water and peptide derivatives, applied in the field of peptide derivatives, can solve problems such as peptides that have not been seen yet, and achieve high application prospects

Inactive Publication Date: 2010-05-12
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there have been no literature reports on peptides used to generate stable small molecule hydrogels, or peptide-based small molecule hydrogels that can exist stably in a large amount of aqueous solution

Method used

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  • Polypeptide derivatives for generating stable micro-molecular hydrogel
  • Polypeptide derivatives for generating stable micro-molecular hydrogel
  • Polypeptide derivatives for generating stable micro-molecular hydrogel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] The synthetic method step of the polypeptide for generating stable small molecule hydrogel of the present invention is as follows:

[0013]

[0014] Wherein, DIPEA is N, N-diisopropylethylamine, Acetone is acetone, I 2 is iodine, triethyl phosphite is triethyl phosphite, DCM is dichloromethane, pyridine is pyridine, TFA is trifluoroacetic acid, spps is the English abbreviation of "polypeptide solid-phase synthesis", TMSBr is trimethylbromosilane, and MeOH is Methanol.

[0015] Step 1, Fmoc-L-Tyr-O t Synthesis of Bu

[0016] 10mmol L-tert-butyl tyrosine and 10 molecules of N,N-diisopropylethylamine are dissolved in 75ml of acetone, and the acetone solution of 75ml of Fmoc-OSu containing 9.8mmol is added under stirring conditions, Stir at room temperature for 12 hours, then separate with silica gel column to obtain 4.4 g of product Fmoc-L-Tyr-O t Bu (i.e. the compound 3 in the above-mentioned synthetic method step), its productive rate is 95.8%, 1 H NMR (300MHz, D...

Embodiment 2

[0028] Synthesis of the polypeptide compound Nap-GFFY(p)-OMe shown in the following structural formula (I).

[0029]

[0030] The first step to the third step are all the same as in Example 1.

[0031] In the fourth step, the compound Nap-GFFY(PO(OFt) 2 )-OMe (that is, in the general formula of compound 6 of Example 1, R 1 for group, R 2 for H, R3 for the synthesis of H)

[0032] Adopt the method for Fmoc solid phase synthesis, step is:

[0033] Step 1, weigh 0.5mmol 2-chlorotrityl chloride resin in a solid-phase synthesizer, add 2.5mL of anhydrous dichloromethane, and feed nitrogen for 5min to make the 2-chlorotrityl chloride resin fully swelling;

[0034] In the 2nd step, dichloromethane is removed from the solid-phase synthesizer that 2-chlorotrityl chloride resin is housed with nitrogen;

[0035] In the third step, 1 mmol of the compound 5 synthesized in the third step was dissolved in 2 mL of anhydrous dichloromethane, and 1 mL (ie 0.5 mmol) was taken, and 0.5 ...

Embodiment 3

[0045] Synthesis of the polypeptide Nap-FFY(p)-OMe shown in the following structural formula (II).

[0046]

[0047] The operation methods and parameters of other synthesis steps are the same as those in Example 2, except that the raw materials for polypeptide synthesis in steps 6-7 of the fourth step are replaced by Fmoc-phenylalanine and naphthaleneacetic acid.

[0048] Thus synthesized to obtain the polypeptide Nap-FFY(p)-OMe as shown in the above structural formula (II), the yield is 94%, 1 H NMR (400MHz, DMSO-d 6 )δ8.63 (d, J=7.324, 1H), 8.39 (d, J=8.518, 1H), 8.28 (d, J=8.216, 1H), 7.90-8.00 (m, 3H), 7.74 (s, 1H ), 7.62(m, 2H), 7.35-7.40(m, 3H), 7.25-7.40(m, 10H), 7.23-7.25(m, 2H), 4.6-4.8(m, 3H), 3.745(s, 3H ), 3.60-3.72(m, 3H), 3.000-3.120(m, 3H), 2.3-2.80(m, 2H). MS: calc.M + =737.25, obsvd.(M+Na) + =760.35.

[0049] The Nap-FFY(p)-OMe molecule of the polypeptide shown in the above structural formula (II) prepared in this example can be well dissolved in aqueo...

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PUM

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Abstract

The invention discloses polypeptide derivatives for generating stable micro-molecular hydrogel and relates to a compound library containing polypeptides. The molecular composition and structure are represented by a compound structural formula below, wherein in the formula, R1 represents aromatic ring derivatives, R2 represents one side chain group of 20 natural amino acids, R3 may be any of H and halogen, R4 may be OMe group or NHMe group, and n is 0 to 3. The micro-molecular hydrogel generated by the polypeptide derivatives can exist stably in a large amount of an aqueous solution, the shape can be well maintained, the micro-molecular hydrogel has high biocompatibility and is widely applied in the fields of tissue engineering, cosmetic, and the like.

Description

technical field [0001] The technical scheme of the present invention relates to a compound library containing polypeptides, in particular to polypeptide derivatives used to generate stable small molecule hydrogels. Background technique [0002] Peptide-based small molecule hydrogels have high biocompatibility and have high potential application value in tissue engineering materials, cosmetics and other fields. However, so far, the known small molecule hydrogels based on polypeptides cannot exist stably in a large amount of aqueous solution and are easily dissolved into a uniform solution, which prevents such hydrogels from being widely used in practical applications. This has been reported in existing literature (Genove E, Shen C, Zhang SG, Semino CE, BIOMATERIALS, 2005, 16, 3341-3351; Ghanaati S, Webber MJ, Unger RE, Orth C, Hulvat JF, Kiehna SE, Barbeck M, Rasic A , Stupp SI, Kirkpatrick CJ, BIOMATERIALS, 2009, 31, 6202-6212) have been reported. So far, there have been n...

Claims

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Application Information

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IPC IPC(8): C07K5/107C07K5/087C07K7/06
Inventor 杨志谋王玲王怀民王景玉
Owner NANKAI UNIV
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