CN112479971B - 2-bromo-1- (7-nitroindoline) hexadecanone compound and preparation method and application thereof - Google Patents
2-bromo-1- (7-nitroindoline) hexadecanone compound and preparation method and application thereof Download PDFInfo
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- CN112479971B CN112479971B CN202011451038.2A CN202011451038A CN112479971B CN 112479971 B CN112479971 B CN 112479971B CN 202011451038 A CN202011451038 A CN 202011451038A CN 112479971 B CN112479971 B CN 112479971B
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
- G01N33/5044—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics involving specific cell types
- G01N33/5058—Neurological cells
Abstract
The invention belongs to the field of caged compounds, and particularly relates to a 2-bromo-1- (7-nitroindoline) hexadecanone compound and a preparation method and application thereof. The compound has a structure shown in a formula (1), wherein R 1 Is selected from C 1‑3 Alkoxy group of (a); r 2 Selected from hydrogen or nitro. According to the 2-bromo-1- (7-nitroindoline) hexadecanone compound disclosed by the invention, a nitroindoline structure and 2-bromohexadecanoic acid are combined through a covalent bond to form a caged compound, the caged compound can be excited and photolyzed under a certain wavelength to release 2-bromohexadecanoic acid, and the caged compound can be used for mechanism research on regulation of neural plasticity in a protein palmitoylation modification process.
Description
Technical Field
The invention belongs to the field of caged compounds, and particularly relates to a 2-bromo-1- (7-nitroindoline) hexadecanone compound and a preparation method and application thereof.
Background
Caged compounds are products formed by the covalent bonding of small biologically active molecules to an inert compound (a caged moiety). After binding, the small bioactive molecules lose activity, but the covalent bonds are sensitive to light, and under the irradiation of light with certain wavelength, the covalent bonds are broken to release the small bioactive molecules to play a role. This photo-activation process is called photolytic cage-lock.
The majority of the caged substances that have been successfully developed are neurotransmitters or ligands such as: MNI-captured-L-glutamate, MNI-captured-NMDA, MNI-captured kainic acid, CNV Dopamine, RuBi-GABA (Rial Verde et al, 2008), and the like; energy substances such as: DMNPE-caged ATP dimonium salt; some important ions are such as: DMNPE-4 AM-captured-calcium, NPE-captured-proton, NPE-captured-HPTS or blockers/agonists of specific receptors such as: NPEC-captured-D-AP 5, MNI-captured-D-aspartate, NPEC-captured-LY 379268 and the like. These caged substances can only act on specific receptors for the study of classical neurotransmission and receptor-mediated physiological and biochemical processes.
The most widely used in the field of neuroscience is caged neurotransmitters. The current cage-locked neurotransmitters are most studied are cage-locked gamma-aminobutyric acid (Caged-GABA) and cage-locked glutamic acid (Caged-Glu). The basic working principle of photolysis of cage-locked neurotransmitters is: after the caged gamma-aminobutyric acid or the caged glutamic acid absorbs light with specific wavelength, the covalent bond bound with neurotransmitter is broken to release the gamma-aminobutyric acid or the glutamic acid, so that the caged gamma-aminobutyric acid or the caged glutamic acid is bound with a corresponding receptor to exert biological effect.
The selection of the proper cage-locked neurotransmitter is the key to the photolytic cage-lock application, and an ideal cage-locked neurotransmitter has the following characteristics to play a good role: (1) at physiological pH, the water-soluble chitosan hydrogel has good water solubility; (2) the product has good stability and can not be hydrolyzed; (3) photolysis release is fast and efficient, and the requirements of synaptic time on the time and concentration of transmitter release can be met; (4) the caged compound, the reaction intermediate product and the photolytic byproduct are all completely inert and have no influence on corresponding receptors, transporters, released neurotransmitter metabolism and the like; (5) the photolysis should be performed under a longer light as much as possible to enhance the penetration of the light into the tissue and avoid damage to the cells.
In neural activities, translational modification of proteins plays an important role. Common protein translation modifications mainly include phosphorylation, methylation, acetylation, ubiquitination, glycosylation, and the like. Wherein, the palmitoylation modification of the protein is a widely-existing and only reversible covalent modification of lipid after translation, and the hydrophobicity of the palmitoylation modified protein is increased, which has important effects on the transportation of the protein, the stability of membrane function, the membrane mass migration of a receptor, the positioning and the function of organelles and the like. The method deeply discusses the regulation mechanism of the palmitoylation modification of the protein and has great significance for understanding a complex signal transduction path.
The traditional method for researching palmitoylation protein mainly adopts protein lysate to carry out ABE/RAC detection and indirectly detects the palmitoylation modification level of protein, and the method has the defects of large error, poor repeatability, complicated treatment process, large sample loss and incapability of reflecting in-situ information of palmitoylation change of protein in cells. Immunohistochemical experiments were even impossible due to the lack of antibodies specifically detecting the level of palmitoylation of the protein.
At present, the role played by protein palmitoylation in regulating neuronal activity is not well understood due to the lack of corresponding tool drugs.
Disclosure of Invention
The invention aims to provide a 2-bromo-1- (7-nitroindoline) hexadecanone compound which can be used for mechanism research of regulating nerve activity by protein palmitoylation.
The second object of the present invention is a process for producing the above-mentioned 2-bromo-1- (7-nitroindoline) hexadecanone compound.
The third purpose of the invention is to provide the application of the 2-bromo-1- (7-nitroindoline) hexadecanone compound.
In order to achieve the above purpose, the technical scheme of the 2-bromo-1- (7-nitroindoline) hexadecanone compound is as follows:
a2-bromo-1- (7-nitroindoline) hexadecanone compound having a structure represented by formula (1):
in the formula (1), R 1 Is selected from C 1-3 Alkoxy group of (a); r 2 Selected from hydrogen or nitro.
According to the 2-bromo-1- (7-nitroindoline) hexadecanone compound disclosed by the invention, a nitroindoline structure and 2-bromohexadecanoic acid are combined through a covalent bond to form a caged compound, the caged compound can be excited and photolyzed under a certain wavelength to release 2-bromohexadecanoic acid, and the caged compound can be used for mechanism research on regulation of neural plasticity in a protein palmitoylation modification process.
Preferably, the 2-bromo-1- (7-nitroindoline) hexadecanone compound is 2-bromo-1- (4-methoxy-7-nitroindoline) hexadecanone, and has the following structural formula:
the technical scheme of the preparation method of the 2-bromo-1- (7-nitroindoline) hexadecanone compound is as follows:
a method for preparing a 2-bromo-1- (7-nitroindoline) hexadecanone compound, comprising the steps of: a nitroindoline compound shown in a formula (2), 2-bromohexadecanoic acid and thionyl chloride are stirred and react in a solvent at the temperature of 60-100 ℃;
preferably, the reaction time is 2-24 h.
In order to ensure higher reaction yield of the raw materials, the mol ratio of the nitroindoline compound shown in the formula (2), the 2-bromohexadecanoic acid and the thionyl chloride is preferably 1 (1-2) to (1-2).
The reaction solvent may be selected from toluene. The concentration of the nitroindoline compound shown in the formula (2) in toluene can be selected from 1-10 mol/L. After the reaction time is reached, post-treatment is carried out. The specific post-treatment can be that the reaction system is cooled to room temperature and then saturated NaHCO is used 3 The solution was quenched at 0 ℃. Then, ethyl acetate was added thereto, and the mixture was extracted 3 times with saturated brine, and the organic phase was added with anhydrous Na 2 SO 4 And (5) drying. Filtering to remove Na 2 SO 4 And concentrating the filtrate under reduced pressure to obtain the product. The product can be further purified by reverse phase liquid chromatography to obtain the target compound.
The following is a description of the use of the above-mentioned 2-bromo-1- (7-nitroindoline) hexadecanone compound.
The 2-bromo-1- (7-nitroindoline) hexadecanone compound has the photolysis caging property, and by utilizing the property, a two-photon microscope can be excited and photolyzed under the excitation wavelength to realize fixed-point accurate release, so that a powerful tool is provided for researching the scientific problem of how to regulate synaptic plasticity in the protein palmitoylation process.
Preferably, the excitation wavelength of the photolytic cage lock is 690-1040 nm.
The application of the 2-bromo-1- (7-nitroindoline) hexadecanone compound in photon imaging.
In the photon imaging technology, the 2-bromo-1- (7-nitroindoline) hexadecanone compound can be excited by specific wavelength light and photolyzed, so that the compound can be used for research on nerve regulation activities.
The application of 2-bromo-1- (7-nitroindoline) hexadecanone compound in regulating nerve activity by protein palmitoylation is provided.
Preferably, the modulated neural activity comprises a change in neuronal dendritic spine morphology and/or modulation of synaptic plasticity.
Different cage-locked substances only act on specific receptors, and the 2-bromo-1- (7-nitroindoline) hexadecanone compound can be used for researching the influence of protein palmitoylation inhibition on the morphology of dendritic spines and the change of intracellular calcium ion concentration, thereby creating good conditions for researching the regulation of neural plasticity.
Drawings
FIG. 1 shows the preparation of the compound obtained in example 2 of the present invention 1 H-NMR chart;
FIG. 2 shows the results of LC-MS detection of the compound obtained in example 2 of the present invention;
FIG. 3 is an HPLC-PDA chromatogram of the compound obtained in example 2 of the present invention;
FIG. 4 is an HPLC-ELSD chromatogram of the compound obtained in example 2 of the present invention;
FIG. 5 is a graph showing comparative changes in synaptic morphology before and after uncaging, obtained by two-photon imaging using the compound obtained in example 2.
Detailed Description
The following examples are provided to further illustrate the practice of the invention.
Specific examples of 2-bromo-1- (7-nitroindoline) hexadecanone compounds of the present invention
Example 1
The 2-bromo-1- (7-nitroindoline) hexadecanone compound of this example has the structural formula:
in other embodiments, R corresponds to formula (1) 2 May be nitro, R 1 And may be ethoxy or propoxy.
Second, specific examples of the process for producing 2-bromo-1- (7-nitroindoline) hexadecanone compound of the present invention
Example 2
The preparation process of the compound of example 1, which is the preparation method of the 2-bromo-1- (7-nitroindoline) hexadecanone compound of this example, specifically includes the following steps:
1) 1g of 4-methoxy-7-nitro-2, 3-indoline (4.892mmol,1.00equiv, 95%) and 2.59g of 2-bromohexadecanoic acid (7.338mmol,1.5equiv, 95%) were dissolved in 10ml of toluene, and thionyl chloride (0.92g,7.338mmol,1.5equiv, 95%) was added and stirred at 80 ℃ for 16 h.
2) Cooling the reaction system to room temperature and then using saturated NaHCO 3 The solution was quenched at 0 ℃. Then, 20mL of an ethyl acetate solution was added thereto, and the mixture was extracted 3 times with saturated brine and anhydrous Na 2 SO 4 And (5) drying. Filtering to remove Na 2 SO 4 And concentrating the filtrate under reduced pressure to obtain the product. Purifying the product by reversed phase liquid chromatography to obtain the target compound (MNI-captured-2-BP) under the following purification conditions: 80g of C18 filler, 40-60 nm; mobile phase A, 0.05% trifluoroacetic acid aqueous solution, mobile phase B: 0.05% trifluoroacetic acid in acetonitrile, gradient elution for 10min (elution time program as shown in table 1); the detection wavelength is 254 nm.
In this example, the reaction scheme is as follows:
the chemical formula of the product 2-bromo-1- (4-methoxy-7-nitroindoline) hexadecanone is as follows: c 25 H 39 BrN 2 O 4 (ii) a 510.21 for accurate molecular weight (Exact masses); molecular Weight (Molecular Weight): 511.49.
In other embodiments, 4-ethoxy-7-nitro-2, 3-indoline, 4-propoxy-7-nitro-2, 3-indoline, 4-methoxy-5, 7-dinitro-2, 3-indoline are selected as nitroindoline compounds to react to obtain the corresponding target compounds.
Wherein R is 1 The alkoxy of C1-3 has no influence on the property of de-caging except the polarity of the compound; r 2 In the case of nitro, the quantum yield of the photolysis process of the caged material is increased by 5-6 times.
Third, Experimental example
Experimental example 1
The compound obtained in Experimental example 2 was subjected to 1 The results of H-NMR are shown in FIG. 1.
H 1 NMR (DMSO-d6,400MHz) delta (ppm) 2 phenylring hydrogen signals appear in the low field region of the spectrum: δ H7.79 (1H, d, J ═ 8.8Hz, H-2), δ H6.97 (1H, d, J ═ 8.8Hz, H-1). Two methyl signals appear in the high field region of the spectrum: δ H3.97 (3H, s, H-3), δ H0.83 (3H, t, J ═ 6.8Hz, H-20),1 methine signal: δ H4.93 (1H, t, J ═ 7.2Hz, H-6),4 methylene signals, δ H4.36-4.25 (2H, m, H-5), δ H3.06 (2H, t, J ═ 8.0Hz, H-4), δ H2.07-1.90 (2H, m, H-7), δ H1.46-1.15 (24H, m, H8-H19).
Experimental example 2
LC-MS detection was performed on the compound obtained in Experimental example 2.
Chromatographic conditions are as follows: the sample was dissolved in DMSO and separated by a C18 reversed-phase ODS high performance liquid chromatography column (HALO 90A C18; length: 30 mm; inner diameter: 3.0 mm; type: 20 μm). Elution was performed with a binary gradient (mobile phase A: water/0.05% TFA; mobile phase B: acetonitrile/0.05% TFA). The elution procedure is shown in table 1.
TABLE 1 LC elution time program
The detection wavelength range was 190-400nm using a Japan Shimadzu PDA detector (SPD-M20A), Lamp D2. The interface parameters are set as follows: interface ESI; DL Temperature 250 deg.c; nebulizing Gas Frow at 1.50L/min; heat Block at 250 ℃; drying Gas: On 15.00L/min. The mass spectrum ion source mode adopts an electrospray ionization positive ion mode, and the detection voltage is +1.15 kV; threshold: 20, scanning speed: 1667 μ/sec.
The LC-MS detection results are shown in FIG. 2: (ES, M/z):511,513[ M + H ] +, corresponding to the molecular weight of the target compound.
The detection results of the HPLC/diode array detector/evaporative light scattering detector (HPLC/PDA/ELSD) are as follows: 2 peaks were identified in the HPLC-PDA chromatogram (detection wavelength 254nm, as shown in FIG. 3), with retention times Rt of 0.891, 0.921, respectively; the peak heights are 1066092.000 and 6318.000 respectively, and the peak heights are 99.411 and 0.589 respectively; the peak area integrals are 929685 and 6434 respectively, and the peak area percentages are 99.313 and 0.687 respectively;
2 peaks are calibrated in an HPLC-ELSD chromatogram (shown in FIG. 4), and retention times Rt are 0.109 and 0.894 respectively; the peak heights are 7197.000 and 251531 respectively, and the peak heights are 2.728 and 97.218 respectively; the peak area integrals were 17628, 711083, respectively, and the peak area% was 2.426, 97.574, respectively. The purity of the target compound was 97.6% as calculated by peak area normalization.
From the above detection results, synthesis of the target compound can be confirmed.
Experimental example 3 application of MNI-captured-2-BP in two-photon imaging field
Culturing neuron cells, carrying out plasmid transfection or specifically staining an isolated brain slice, and imaging by using a two-photon microscope under a specific wavelength condition.
MNI-caged-2-BP was dissolved in artificial cerebrospinal fluid (126mM NaCl,3mM KCl,1.25mM NaH) 2 PO 4 ,2mM MgSO 4 ,24mM NaHCO 3 ,2mM CaCl 2 10mM glucose, 95% O 2 /5％CO 2 Continuous saturation), the drug was continuously perfused at a flow rate of 1mL/min at room temperature. An acousto-optic driven two-photon microscope high-speed living body imaging system (Femtonics, wavelength 690-. The cage unlocking operation is carried out according to the following 3 steps:
selecting ROI and performing XYZ layer scanning in AO mode. The resolution was 512X512, z step 0.4 μm, z depth 1-3 μm, laser wavelength 920nm, and power 1.85W.
Continuously perfusing MNI-captured-2 BP for 5-10min, switching to a Galvo mode in the same focal plane, exciting and setting the wavelength to be 720nm in a Line scan mode to enable the MINI-captured-2-BP to be accurately unlocked at the dendritic spine position of the ROI, wherein the scanning frequency is 0.1-100Hz, and the power is 2.08W.
And thirdly, carrying out XYZ layer scanning again, and keeping the same as the step 1. And detecting the influence of the blocking of the palmitoylation of the intracellular protein caused by 2-BP before and after unlocking on the morphology of the dendritic spines and the change of the intracellular calcium ion concentration. The results of the pictures processed by MES v.6.3.7480(Femtonics Ltd, Hungary) software are shown in fig. 5.
As shown in FIG. 5, the dendritic spines are labeled by GFP transfection on neurons, and after 720nm laser caging release operation, 2-BP is released to weaken fluorescence, so that the dendritic spines shrink. Indicating that palmitoylation modification of the arrestin causes plastic change of dendritic spine shape.
In summary, the caged compound provided by the invention can be used as a new tool drug, is excited and photolyzed under 720nm wavelength by virtue of a two-photon microscope to realize fixed-point precise release, and provides a powerful tool for researching how the protein palmitoylation process regulates synaptic plasticity.
Claims (10)
- A2-bromo-1- (7-nitroindoline) hexadecanone compound characterized by having a structure represented by formula (1):
in the formula (1), R 1 Is selected from C 1-3 Alkoxy of (2); r 2 Selected from hydrogen or nitro;the preparation method of the 2-bromo-1- (7-nitroindoline) hexadecanone compound comprises the following steps:a nitroindoline compound shown in a formula (2), 2-bromohexadecanoic acid and thionyl chloride are stirred in a solvent for reaction at a temperature of between 60 and 100 ℃;
- 2. 2-bromo-1- (7-nitroindolino) hexadecanone compound according to claim 1, which is specifically 2-bromo-1- (4-methoxy-7-nitroindolino) hexadecanone.
- 3. A process for producing a 2-bromo-1- (7-nitroindoline) hexadecanone compound according to claim 1 or 2, which comprises the steps of: a nitroindoline compound shown in a formula (2), 2-bromohexadecanoic acid and thionyl chloride are stirred in a solvent for reaction at a temperature of between 60 and 100 ℃;
- 4. the process for producing 2-bromo-1- (7-nitroindoline) hexadecanone compound according to claim 3, wherein the reaction time is 2 to 24 hours under stirring.
- 5. The process for producing 2-bromo-1- (7-nitroindoline) hexadecanone compound according to claim 3 or 4, wherein the molar ratio of the nitroindoline compound represented by the formula (2), 2-bromohexadecanoic acid and thionyl chloride is 1 (1-2) to (1-2).
- 6. Use of a 2-bromo-1- (7-nitroindoline) hexadecanone compound according to claim 1 or 2 for photolytic caging.
- 7. The use according to claim 6, wherein the excitation wavelength of photocaging is 690-1040 nm.
- 8. Use of a 2-bromo-1- (7-nitroindoline) hexadecanone compound according to claim 1 or 2 in photonic imaging.
- 9. Use of a 2-bromo-1- (7-nitroindoline) hexadecanone compound according to claim 1 or 2 for modulation of neuronal activity by protein palmitoylation.
- 10. The use of claim 9, wherein the modulated neural activity comprises a change in neuronal dendritic spine morphology and/or modulation of synaptic plasticity.
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| CN104011020A (en) * | 2011-10-03 | 2014-08-27 | 弗姆托尼克斯有限责任公司 | Use Of Photocleavable Compounds |
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| WO2000055133A1 (en) * | 1999-03-18 | 2000-09-21 | Medical Research Council | 1-acyl-7-nitroindoline derivatives, their preparation and their use as photocleavable precursors |
| WO2008094922A1 (en) * | 2007-01-31 | 2008-08-07 | Philadelphia Health & Education Corporation, D/B/A Drexel University College Of Medicine | Photolabile dinitroindolinyl based compounds |
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