Moxifloxacin drug derivatives as well as preparation method and application thereof

A technology of moxifloxacin and derivatives, which is applied in the field of biomedical materials, can solve the problems of less application of fluorescent properties and drug activity, and few researches on drug fluorescence properties, and achieve excellent antibacterial effect, good antibacterial activity, and maintain activity. Effect

Active Publication Date: 2021-02-26
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] As a kind of broad-spectrum antibacterial drugs, quinolone antibiotics have been widely used in clinic due to their high antibacterial properties; however

Method used

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  • Moxifloxacin drug derivatives as well as preparation method and application thereof
  • Moxifloxacin drug derivatives as well as preparation method and application thereof
  • Moxifloxacin drug derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Preparation of a kind of moxifloxacin drug derivative (MXF-P)

[0061] The synthetic route is as follows:

[0062]

[0063] MXF-P: Dissolve compound 1 (304mg, 0.6mmol) and MXF-HCl (219mg, 0.5mmol) in the mixed solution of MeCN:DMF=9mL:1mL, add KHCO 3 (84mg, 1.0mmol); the reaction mixture was heated to 90°C and reacted for 12 hours. After the solvent was removed by rotary evaporation under reduced pressure, water was added to the mixture. It was then extracted with DCM (3×30ml); the combined organic layers were washed with anhydrous Na 2 SO 4 Drying, concentration, and silica gel column purification (eluent DCM:MeOH=20:1) gave yellow solid MXF-P with a yield of 58%. 1 H NMR (500MHz, CDCl 3 )δ15.16(brs,1H),8.37(s,1H),7.84–7.75(m,9H),7.71–7.65(m,7H),4.02–3.99(m,1H),3.80–3.71(m, 3H),3.65–3.55(m,5H),3.17(brs,1H),2.76(brs,1H),2.53(brs,1H),2.39–2.23(m,3H),1.82–1.41(m,10H) ,1.37–1.17(m,5H),0.99–0.92(m,2H). 13 C NMR (125MHz, CDCl 3 )δ176.7, 167.2, 153.8 (d, J C-F =24...

Embodiment 2

[0065] Preparation of anion in the structure of moxifloxacin derivatives

[0066] will get Br - The compound MXF-P was dissolved (0.2mmol, 166mg) in acetone, and an aqueous solution of potassium hexafluorophosphate (0.3mmol, 55mg) was added and stirred for 2h. The mixture was added water and filtered. The filtered solid is washed with water to remove inorganic salts, and the product containing hexafluorophosphate anion can be obtained after drying.

Embodiment 3

[0068] Characterization of Absorption and Fluorescence Spectra of Moxifloxacin Derivatives

[0069] Figure 1A Based on the absorption spectrum of the material MXF-P obtained in Example 1 in DMSO, it can be seen that the main absorption peak of the molecule is around 365nm; Figure 1B It is the fluorescence emission spectrum of MXF-P in DMSO solvent and solid state, it can be seen that the emission peak of the molecule is mainly around 475nm; Figure 1C for with H 2 O content increased in MXF-P (10 μM) in DMSO / H 2 Fluorescence emission spectrum in O(v / v) mixed solvent; when the molecule is in the solution of DMSO, the luminescence is weak, and it can be found that the fluorescence intensity is continuously enhanced with the addition of water. When the water content reaches 90%, The fluorescence intensity reaches a maximum. This phenomenon is due to the continuous enhancement of fluorescence due to the aggregation of MXF-P molecules as the proportion of poor solvent water in...

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Abstract

The invention belongs to the field of biomedical materials, and discloses moxifloxacin drug derivatives as well as a preparation method and application thereof. The moxifloxacin drug derivative has astructure shown as a formula I, wherein R is independently an organic cation of triphenylphosphine salt, pyridinium salt and quaternary ammonium salt; x is a monovalent anion; and n is any integer from 1 to 17. The invention also discloses a preparation method of the moxifloxacin drug derivative. The moxifloxacin drug derivative disclosed by the invention has an aggregation-induced emission property, can realize rapid staining recognition on microorganisms, and shows the characteristics of specificity, high efficiency and sensitivity. The moxifloxacin drug derivative disclosed by the inventionhas an excellent antibacterial effect. The moxifloxacin drug derivative disclosed by the invention is used for preparing reagents for specific dyeing of mitochondria and dyeing of microorganisms withnegative charges on the surfaces, and is also used for preparing reagents and antibacterial agents for distinguishing dead and living states of microorganisms.

Description

technical field [0001] The invention belongs to the field of biomedical materials, and in particular relates to a class of moxifloxacin drug derivatives and a preparation method and application thereof. Background technique [0002] In clinical practice, bacterial infection causes a variety of diseases and seriously threatens human health. In the antibacterial process, rapid diagnosis and accurate treatment of bacterial species are very important. At present, the main method used to distinguish bacterial species is Gram staining. This method is complicated to operate, time-consuming and laborious, and cannot realize constant in-situ monitoring of live bacteria. Therefore, it is very important to develop accurate and rapid bacterial identification and diagnostic reagents. [0003] Organic small molecule fluorescent probes have been widely used in biological rapid detection, biological imaging and treatment, and it has the characteristics of low cost, simple operation and hi...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K11/06G01N21/64C12Q1/00A61P31/04
CPCC07D471/04C09K11/06G01N21/6428C12Q1/00A61P31/04G01N2021/6432
Inventor 唐本忠秦安军王柄楠胡蓉蓉赵祖金王志明
Owner SOUTH CHINA UNIV OF TECH
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