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Taxol-based small molecule hydrogel-nanosphere transmission system and preparation method thereof

A technology of small molecule water and paclitaxel, which is applied in the direction of non-active ingredients of high molecular compounds, peptides, etc., to achieve the effect of simple synthesis

Inactive Publication Date: 2011-07-13
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there have been no reports of using small molecular peptides to link hydrophobic drugs to form nanospher

Method used

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  • Taxol-based small molecule hydrogel-nanosphere transmission system and preparation method thereof
  • Taxol-based small molecule hydrogel-nanosphere transmission system and preparation method thereof
  • Taxol-based small molecule hydrogel-nanosphere transmission system and preparation method thereof

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Embodiment 1

[0011] (1) Fmoc-L-Tyr(PO(OEt) 2 )-OH (compound 5) synthesis, the synthesis steps are shown in the appendix figure 1

[0012] Step 1: Fmoc-L-Tyr-O t Synthesis of Bu(Compound 3)

[0013] Weigh 5mmol (1.185g) L-tert-butyl tyrosine and dissolve it in 30mL of acetone solution, add 5 molecules of N,N-diisopropylethylamine, and gradually add 5mmol (1.65g ) an acetone solution of fluorenyl methaneoxycarbonyl succinimide, react overnight at room temperature, remove the solvent with a rotary evaporator, and then separate with a silica gel column to obtain 2.2 g, with a yield of 95.8%. 1 H NMR (300MHz, DMSO-d 6 )δ8.03-8.05 (d, 2H), 7.81-7.85 (t, 2H), 7.56-7.59 (t, 2H), 7.46-7.48 (m, 2H), 7.19-7.21 (d, 2H), 6.81- 6.83(d, 2H), 4.30-4.40(m, 3H), 4.2-4.24(m, 1H), 3.30-3.36(m, 2H), 1.50(s, 9H).MS: calc.M + =459.2, obsvd.(M+1) + =459.8.

[0014] The second step: Fmoc-L-Tyr(PO(OEt) 2 -OH

[0015] Dissolve 8 mmol of triethyl phosphite in 40 mL of dichloromethane, add 3.3 mmol of iodine...

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Abstract

The invention relates to a taxol-based small molecule hydrogel-nanosphere transmission system and a preparation method thereof. The invention relates to a method for preparing a taxol prodrug by connecting folic acid with taxol through short peptide. Nanospheres with dimension of about 50 nm and small molecule hydrogel are obtained by performing enzyme catalysis on the obtained compound. The preparation method comprises the following steps of: synthetizing small molecule peptide by a solid-phase synthetic method; reacting a side chain amino group of polypeptide lysine with a compound derived from a taxol 2' hydroxyl position; and connecting with folic acid molecules to obtain gelatinizing and balling precursor molecules, wherein the precursor molecules have targeted effects and high dissolubility and are self-assembled into the nanospheres of about 50 nm through enzyme catalysis. Therefore, the taxol novel transmission system solves the problems that the taxol has low dissolubility and does not have specificity to cells, and is expected to solve the problems of toxic or side effects and low bioavailability.

Description

technical field [0001] The technical scheme of the present invention relates to a paclitaxel derivative and a synthesis method, as well as the formation of nanospheres catalyzed by means of enzyme catalysis, specifically the preparation of novel targeted polypeptide-modified paclitaxel derivative nanospheres. Background technique [0002] Paclitaxel is a new generation of broad-spectrum anticancer drug that was clinically used in the 1990s. Due to its poor water solubility, most paclitaxel preparations currently used clinically use a mixture of polyoxyethylene castor oil (Cremophor EL) and absolute ethanol (1:1) as a co-solvent. Dilute with normal saline or 5% glucose to a final concentration of 0.4-1.4mmolL before administration -1 , these co-solvents can cause a variety of adverse reactions, including allergic reactions and neurotoxicity. In addition, the small particles formed by polyoxyethylene castor oil in the blood circulation can wrap paclitaxel molecules, hinderin...

Claims

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Application Information

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IPC IPC(8): C07K7/06A61K47/42A61K47/18A61K47/65A61K47/66
Inventor 杨志谋王玲孔德领王怀民杨翠红
Owner NANKAI UNIV