Fluorescent probe for monitoring lipid peroxidation processes in different subcellular organelles

A lipid peroxidation and fluorescent probe technology, applied in the field of fluorescent probes, can solve the problems of high price, cumbersome synthesis and preparation process, and high cost, and achieve the effects of easy long-term storage, sensitive response, and stable properties

Active Publication Date: 2015-10-28
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there have been some reports using fluorescence imaging to monitor the occurrence of LPO, there are few reported LPO probes with subcellular organelle targeting, mainly based on the commercial LPO probe C11-BODIPY 581 / 591 , and its synthesis and preparation process is relatively cumbersome, resulting in high cost and high price, which is not conducive to wide use. 581 / 591 Performed structure derivation, synthesis complex
There are no reports on more other subcellular organelle-targeted LPO probes

Method used

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  • Fluorescent probe for monitoring lipid peroxidation processes in different subcellular organelles
  • Fluorescent probe for monitoring lipid peroxidation processes in different subcellular organelles
  • Fluorescent probe for monitoring lipid peroxidation processes in different subcellular organelles

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] Add 500 mg of tetramethylfluoroborate and 129 mL of cinnamaldehyde into two-necked reaction flasks, then add 500 mL of piperidine as a catalyst, and 4? After removing toluene, silica gel column separation (eluent: dichloromethane: n-hexane = 1:4) gave 155 mg of a purple solid with a yield of 23%.

Embodiment 2

[0039]

[0040] Add 500 mg of tetramethylfluoroborate and 94 mL of cinnamaldehyde into two-necked reaction flasks, then add 500 mL of piperidine as a catalyst, and 4? After removing toluene, silica gel column separation (eluent: dichloromethane: n-hexane = 1:4) yielded 194 mg of purple solid with a yield of 31%.

[0041]

[0042] Dissolve 100 mg of the product obtained in the previous step in DMSO, add excess morpholine 100 mL, 24 mg K 2 CO 3 and 30mg KI, reacted at 60°C for 12h, washed the reactant with CH 2 Cl 2Extract, keep the organic phase, dry over anhydrous magnesium sulfate, spin dry under reduced pressure, and separate on a silica gel column (dichloromethane: methanol = 20:1 as the eluent) to obtain 81 mg of a purple solid with a yield of 75%.

Embodiment 3

[0044]

[0045] Add 500 mg of tetramethylfluoroborate and 88 mL of cinnamaldehyde into two-necked reaction flasks, then add 500 mL of piperidine as a catalyst, and 4? After toluene was removed, silica gel column separation (eluent: dichloromethane: n-hexane = 1:4) gave 217 mg of a purple solid with a yield of 35%.

[0046]

[0047] Dissolve 100 mg of the product obtained in the previous step in acetone, add 50 mg of excess tertiary amine, KI 30 mg, react at 60°C for 12 h, concentrate the reaction solution, and add diethyl ether, a dark purple solid precipitates out, which is the target product. Dissolve the fluorescent probe in methanol, add 1000 mg of potassium periodate, stir at 50°C for 24 hours, then spin dry the reaction solution under reduced pressure, dissolve it in a small amount of dichloromethane, filter to remove inorganic salts, keep the filtrate, and spin dry again under reduced pressure , to obtain 141 mg of dark purple solid, which is a fluorescent probe w...

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Abstract

The invention discloses a fluorescent probe for monitoring lipid peroxidation processes in different subcellular organelles, and belongs to the field of fine chemical engineering. The fluorescent probe is prepared through the steps of: enabling fluorine boron pyrrole derivatives to react with cinnamic aldehyde, wherein piperidine is used as a catalyst, and a 4 angstrom molecular sieve is used as a dehydrating agent; and performing quaternization on the obtained reactant so as to obtain molecules of the fluorescent probe. The probe contains active groups such as triphenylphosphine cations, morpholine and quaternary ammonium salt cations, the probe has a single-minded subcellular organelle targeting property because of the different active groups, and the probe can be optionally positioned on subcellular organelles such as mitochondria, lysosomes and cell membranes. The probe has zero toxin and zero side effects and is suitable for monitoring the lipid peroxidation processes in the subcellular organelles in different physiological processes through a fluorescent microscope or flow type cell analyzing technology. The probe is stable in solid condition nature and easy to store for a long time, an intuitional succinct detecting reagent with low cost is provided for inquiring processes relevant to the lipid peroxidation in cells, and microcosmic structural information is provided for detection by a subcellular organelle targeting property function.

Description

technical field [0001] The invention relates to a class of fluorescent probes for monitoring lipid peroxidation process in different subcellular organelles, belonging to the technical field of fine chemicals. Background technique [0002] Lipid peroxidation (Lipid peroxidation, LPO) has been clearly reported as the main pathogenesis of many diseases, such as cancer, atherosclerosis, nervous system diseases, and so on. The essence of LPO is a chain reaction of free radicals based on unsaturated fatty acids, which are usually triggered by reactive oxygen species (ROS), and its pathogenic damage to the body is often beyond ROS to the inner membrane of cells. Oxidative damage to the structure. The malignant results brought by LPO to the body are due to the continuous chain reaction, which will continuously release active substances, such as malondialdehyde, which will trigger a variety of destructive reactions and damage the body's activity. Therefore, studying the LPO process...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F5/02G01N21/64C07F9/50
Inventor 肖义张新富
Owner DALIAN UNIV OF TECH
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