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Abamectin b1a fluorescent marker and its application

A fluorescent marker, abamectin technology, applied in the field of chemical biology, can solve the problems of technical means limitation, no further application, high cost, wide application prospect, convenient chemical biology research, good pharmacology The effect of the application foreground

Inactive Publication Date: 2016-02-24
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the most widely used method in biology is immunofluorescence, but the cost is too high
With the rapid development of chemical biology in recent years, the use of chemical means to solve biological problems is gradually being accepted by researchers. However, it is theoretically feasible to use chemiluminescent methods for the study of the effects of abamectin. Previously, Schaffer The synthesis of luminol-Invermectin fluorescent markers has not been further applied due to many defects and limitations of technical means

Method used

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  • Abamectin b1a fluorescent marker and its application
  • Abamectin b1a fluorescent marker and its application
  • Abamectin b1a fluorescent marker and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of embodiment one 5-abamectin B1a ester (compound A-1)

[0025] Dissolve 6-bromohexanoic acid and sodium azide in DMF, at 80-100°C for 3-6 hours, dilute the reaction mixture with DCM, wash the organic phase with HCl solution, and wash the organic phase with anhydrous sodium sulfate Dry, filter, and spin out the organic phase to obtain 6-azidocaproic acid as a colorless oily compound;

[0026] Dissolve Abamectin B1a in DCM together with imidazole, DMAP, TBDMS-Cl, react at room temperature for 5-8 hours, add water to the reaction solution, extract the reaction solution with DCM, and use saturated chlorination for the organic phase The sodium solution was washed and separated, and the organic phase was dried with anhydrous sodium sulfate, filtered and distilled to obtain the compound avermectin B1a-TBDMS with the 5-hydroxyl protected.

[0027] The prepared compound 6-azidohexanoic acid and abamectin B 1a -TBDMS undergoes esterification reaction under DCC and ...

Embodiment 2

[0034] The preparation of embodiment two 4''-abamectin B1a ester (compound A-2)

[0035] Compound 6-azidocaproic acid and avermectin B prepared in embodiment one 1a Carry out esterification reaction under DCC, DMAP condition, obtain white solid compound Abamectin B1a-N 3 -2; then abamectin B 1a -N 3 -2 and the compound 4-ethynyl-1,8-naphthalimide obtained in Example 1 were dissolved in DMSO: water: tert-butanol (V:V:V=1:1:1), and click chemistry reaction to obtain the final compound fluorescently labeled Abamectin B 1a Compound A-2; wherein the reaction conditions and separation conditions are the same as in Example 1. The target compound A-2 was tested by TOF-MS-ES+, 1 HNMR, 13 CNMR for determination. Materialized data:

[0036] 1 HNMR (500MHz, DMSO-d 6 ):δ9.03(d,1H),8.77(s,1H),8.39(t,3H),7.98(d,1H),7.77(t,1H),5.68(br,d,2H),5.60( d,1H),5.53(m,1H),5.47(s,1H),5.43(dd,2H),5.38(s,1H),5.25(d,1H),5.13(s,1H),5.02(t ,1H),4.96(d,1H),4.75(m,1H),4.59(s,1H),4.43(t,3H),4.32(d,...

Embodiment 3

[0039] The measurement of the fluorescent characteristic of embodiment three Abamectin B1a fluorescent markers

[0040] Weighed 1.0 mg of compounds A-1 and A-2 respectively, dissolved them in DMSO, diluted them with PBS buffer to a concentration of 20 μg / ml, and measured the fluorescence characteristics of the fluorescent markers using a PTI steady-state fluorometer.

[0041] The results showed that the maximum excitation wavelength of A-1 was 375nm and the emission wavelength was 480nm; the maximum excitation wavelength of A-2 was 370nm and the emission wavelength was 475nm. After A-1 and A-2 were dissolved in DMSO, bright blue fluorescence could be observed under 365nm ultraviolet light. figure 1 Show Abamectin B 1a Fluorescent characteristics of fluorescent markers A1 and A2 under the excitation wavelength of 365nm.

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Abstract

The invention discloses an abamectin B1a fluorescence indicator, which is a compound shown in a formula A-1 or A-2 in the specification. The abamectin B1a fluorescence indicator can be used as a pesticide, an insect physiological indicator and an insect cell fluorescence tracer, and can also be used as an anticancer agent.

Description

technical field [0001] The invention belongs to the field of chemical biology, and relates to an abamectin B1a fluorescent marker and an application thereof. Background technique [0002] Avermectins are a group of macrolide antibiotic insecticides and acaricides, which were isolated from the biological fermentation of Streptomecesavermitillis by Japanese scientists and Merck in 1975. There are 8 natural Avermectins Components are A1a, A1b, A2a, A2b, B1a, B1b, B2a, B2b according to the difference of X-Y, R1, R2 substituents, wherein the activity of abamectin B1a is the highest. The initial explanation of its mechanism of action is that the stimulation of GABA causes nerve endings to release a large amount of GABA, and can promote the combination of GABA and secondary neuron cell membrane or effector cell membrane, resulting in a long-term and high-intensity inhibitory effect. Paralyzed and dead worms, to achieve the insecticidal effect; but later studies found that at lower...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/08C07H1/00C09K11/06A01N43/90A61K31/706A61P35/00A01P7/04G01N21/64G01N21/31
Inventor 陶黎明吴伟黄青春张阳徐文平李荻秋周高辉罗明明
Owner EAST CHINA UNIV OF SCI & TECH
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