CN110981742A - Phenylalanine derivative with aggregation-induced emission property and preparation and application thereof - Google Patents
Phenylalanine derivative with aggregation-induced emission property and preparation and application thereof Download PDFInfo
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- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
The invention relates to a phenylalanine derivative with aggregation-induced emission (AIE) property, a preparation method thereof and application thereof in constructing peptide fluorescent probes, wherein the structure of the phenylalanine derivative is shown as a formula (I). The invention has the following beneficial effects: the invention provides a phenylalanine derivative with AIE property, which can be further applied to fluorescent polypeptide synthesis and protein labeling and provides a new way for the construction of peptide AIE fluorescent probes.
Description
(I) technical field
The invention relates to a phenylalanine derivative with aggregation-induced emission (AIE) property, and a preparation method and application thereof.
(II) background of the invention
The basic strategy of such probes is to combine fluorescent molecules with protein amino acids, such as carboxyfluorescein (FAM), fluorescein thiocyanate (FITC), heptamethine cyanine dye (Cy7), carboxyrhodamine 110 (carbo-xhydamine 110) and other classical fluorescent dyes at the N-terminal of amino acids or the side chains of Lys and Cys, Edans is linked to the side chains of Glu and Asp, to introduce a fluorescent marker for the purpose of detection, labeling and imaging, while such methods for incorporating fluorescent molecules externally to amino acids require special protection reaction sites and additional steps to incorporate into the site to recognize specific fluorescent markers for targeting of tumor cells, and for incorporation of fluorescent markers for targeting of peptides, such as E-RGD, RGD-binding to tumor cells, RGD-3, RGD-binding to a tumor cell targeting sequence, such as a targeting peptide-binding protein, RGD-binding to a tumor cell targeting sequence, and targeting of RGD-3, RGD-binding to a tumor cell targeting sequence, and targeting of a tumor cell growth-stimulating tumor cell growth-like, and targeting peptides, such as a tumor growth-promoting cell growth-stimulating factor, and tumor growth factor binding to a tumor cell targeting peptide-like, and tumor growth factor, such as a tumor growth factor, and tumor growth factor, wherein the like, and tumor growth factor binding to a tumor cell targeting peptide-RGD-expressing a tumor cell targeting protein is a tumor cell targeting peptide-RGD-expressing a tumor-like.
Disclosure of the invention
The invention aims to provide a phenylalanine derivative with AIE fluorescence property, a preparation method thereof and application thereof in peptide fluorescent probes.
The technical scheme adopted by the invention is as follows:
a phenylalanine derivative with aggregation-induced emission (AIE) property has a structure shown in formula (I):
the present invention also relates to a method for preparing said phenylalanine derivative, said method comprising:
(1) protecting 4-iodine-D-phenylalanine amino by using Boc anhydride to obtain a compound (II);
(2) the compound (II) and the pinacol ester diboron are subjected to PdCl in a DMF solvent at 70-80 ℃ under the protection of nitrogen2(dppf) is used as a catalyst, carrying out suzuki reaction in the presence of KOAc, and separating and purifying after the reaction is finished to obtain a compound (III);
(3) compound (III) with triphenylbromoethylene in THF and H2In an O mixed solvent, Pd (pph3)4 is used as a catalyst under the protection of nitrogen at 70-80 ℃, and K is added2CO3Carrying out a suzuki reaction in the presence of the compound (IV), and separating and purifying after the reaction is finished to obtain a compound (IV);
(4) removing Boc protecting group from compound (IV) to obtain compound (I);
in the step (2), the compound (II), the diboron pinacol ester and PdCl2The ratio of the amounts of substances of (dppf) and KOAc is preferably 1:1.5:0.06: 2.8. Specifically, the separation and purification method in the step (2) is column chromatography, and dichloromethane: and (3) taking mixed liquor with the volume ratio of the A being 30:1 as eluent, collecting target components, and drying to obtain the compound shown in the formula (III).
In the step (3), the compound (III), triphenylbromoethylene and Pd (pph)3)4、K2CO3The amount of the substance(s) is preferably 1:1.2:0.05: 3; THF H in solvent2The volume ratio of O is 10: 1. Specifically, the separation and purification method in the step (3) is column chromatography, and dichloromethane: and (3) taking the mixed solution with the volume ratio of the A to the A of 15:1 as an eluent, collecting a target component, and drying to obtain the compound of the formula (IV).
The fluorescent compound of the formula (I) replaces the phenylalanine to be embedded into integrin targeting c (RGDFK) to construct AIE fluorescent cyclic peptide, and when the AIE fluorescent cyclic peptide is specifically combined with integrins α v β 3, AIE luminescence is generated due to aggregation limited intramolecular rotation (RIR).
The invention has the following beneficial effects: the invention provides a phenylalanine derivative with AIE property, which can be further applied to fluorescent polypeptide synthesis and protein labeling and provides a new way for the construction of peptide AIE fluorescent probes.
(IV) description of the drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of the compound (III).
FIG. 2 is a nuclear magnetic hydrogen spectrum of Compound (IV).
FIG. 3 is a nuclear magnetic hydrogen spectrum of Compound (I).
FIG. 4 is a nuclear magnetic carbon spectrum of Compound (I).
FIG. 5 is a nuclear magnetic hydrogen spectrum of the compound (V).
FIG. 6 is a LC-MS diagram of Compound (VI).
FIG. 7 is a LC-MS diagram of Compound (VII).
FIG. 8 is a LC-MS diagram of Compound (VIII).
FIG. 9 is a graph showing the fluorescence spectrum of compound (VIII) at a concentration of 40. mu.M in dimethyl sulfoxide and PBS.
FIG. 10 shows fluorescence spectra of different concentrations of compound (VIII) in PBS (1% DMSO).
(V) detailed description of the preferred embodiments
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
example 1: synthesis of Compound (I)
(1) 2.0g (5.12mmol) of Compound II was dissolved in 3mL of anhydrous DMF, and 1.9g (7.67mmol) of pinacol diborate and PdCl were added2(dppf)224.3mg (0.306mmol) and 1.4g (14.3mmol) of potassium acetate were reacted at 80 ℃ for 12 hours under nitrogen. TLC spot plate reactionComplete (ninhydrin color development after TFA fumigation), add 50mL each of dichloromethane and water, extract 2 times to collect the organic phase. The extract was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was removed by rotary evaporation under reduced pressure, and the concentrate was subjected to silica gel column separation (dichloromethane: methanol: 30:1, v/v) to obtain compound iii1.82g as a colorless oil in 91% yield. The nuclear magnetic hydrogen spectrum of compound III is shown in fig. 1, (1H NMR (500MHz, CDCl3) δ 7.77(d, J ═ 7.8Hz,2H),7.21(d, J ═ 7.5Hz,2H), 4.94(d, J ═ 7.0Hz,1H),4.61(d, J ═ 5.5Hz,1H),4.14(q, J ═ 7.1Hz,1H), 3.18(ddd, J ═ 51.3,13.9,5.6Hz,2H),1.35(s,12H), 1.32-1.20 (m,9H).
(2) 939mg (2.4mmol) of compound (III) are accurately weighed, 670.4mg (2mmol) of triphenylbromoethylene and Pd (PPh) are added3)4115.55mg (0.1mmol), potassium carbonate 828mg (6mmol), dissolved in 3mL tetrahydrofuran solution and 300. mu.L ddH added2And O. The reaction was carried out for 8 hours at 80 ℃ under nitrogen protection. After the completion of the reaction was monitored by TLC, an equal volume of ethyl acetate and water was added, and the organic phase layer was collected by extraction, washed with saturated sodium chloride water and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation under reduced pressure, and the concentrate was subjected to silica gel column separation (dichloromethane: methanol 15:1, v/v) to collect 1.18g of a yellow oil, which was compound IV in 95% yield. The nuclear magnetic hydrogen spectrum of compound IV is shown in fig. 2, (1H NMR (500MHz, CDCl3) δ 7.11-7.06 (m,3H), 7.06-6.94 (m,12H),6.88(s,4H),4.17(s,1H),2.87(d, J ═ 210.4Hz,2H), 1.30-1.24 (m,9H).
(3)1.18g of compound IV is added with 20mL of HCl-dioxane solution, stirred for 1h at normal temperature, decompressed and concentrated, added with ether, filtered and collected to obtain a filter cake as a white solid compound (I). The nuclear magnetic hydrogen spectrum of compound (I) is shown in fig. 3, 1H NMR (500MHz, DMSO) δ 8.48(s,2H),7.17 to 7.07 (m,9H),7.06(d, J ═ 8.1Hz,2H),7.01 to 6.94(m,6H),6.92(d, J ═ 8.2Hz, 2H),4.06(t, J ═ 6.4Hz,1H),3.09 to 2.98(m, 2H). The nuclear magnetic carbon spectrum of the compound (I) is shown in figure 4.
Example 2: construction of AIE fluorescent probes
(1) 1.0g (2.39mmol) of the compound (I) and 1.2g (3.58mmol) of Fmoc-OSU were dissolved in 30mL of a solution of DMF, and 1.2mL of DIEA was added thereto to conduct a reaction at 40 ℃ for 4 hours. After the completion of the reaction was monitored by TLC, methylene chloride and water were added, and the organic phase layer was collected by extraction. The solvent was removed by rotary evaporation under reduced pressure, and the concentrate was subjected to silica gel column separation (dichloromethane: methanol 20:1, V/V) to collect 1.58g of a white solid compound, which was the compound V. The nuclear magnetic hydrogen spectrum of compound V is shown in fig. 5, H NMR (500MHz, DMSO) δ 7.93-7.82 (m,2H),7.62(dd, J ═ 6.7,3.3Hz, 2H), 7.44-7.33 (m,2H), 7.30-7.21 (m,2H), 7.12-7.00 (m,9H),6.92(dd, J ═ 19.3,7.3Hz,8H),6.77(d, J ═ 7.8Hz,2H),4.26(dd, J ═ 9.6,7.0Hz,1H), 4.10(dt, J ═ 17.6,7.4Hz,2H),3.94(s,1H),3.02(d, J ═ 11.3Hz,1H), 2.82-2.71 (m,1H).
(2) Synthesis of Compound (VI) solid phase synthesis of the polypeptide was used: Fmoc-Arg (Pbf) -OH 389.3mg (0.6mmol), CTC resin 200mg (0.6mmol) and 3mL of methylene chloride were added to a solid phase synthesizer, and 130. mu.L of DIEA (0.8mmol) was dissolved and reacted for 40min, and then the reaction solution was withdrawn. DMF wash 3 times and methanol wash 2 times. Adding 20% piperidine in DMF to remove Fmoc protection, extracting reaction solution after 20min, and washing with DMF for 3 times. Fmoc-Lys (Boc) -OH468.5mg (0.6mmol), HBTU 380mg (0.6mmol) and DIEA 99. mu.L (0.6mmol) were added and reacted for 30-40 min. And (4) pumping out the reaction liquid after the detection reaction of the amino detection reagent is completed. Add 20% piperidine in DMF to deprotect for 20min, and wash with DMF. The peptide chain was extended by the same method and amount of substances in the order Fmoc-Lys (Boc) -OH, Compound (V), Fmoc-Asp (OtBu) -OH, Fmoc-Gly-OH. After completion, 10mL of a dichloromethane solution of 2TFA was added, the reaction was carried out for 10min, the filtrate was collected, the pH was adjusted to neutrality, methylene chloride was added thereto, the organic phase was extracted and collected, and the solvent was removed by rotary evaporation under reduced pressure to obtain 252.6mg of compound (VI) as a white solid. The LC-MS spectrum of compound (VI) is shown in FIG. 6, C69H89N9O13S[M+H]1284.63, found1284.75.
(3) The resulting compound (VI) was dissolved in 25mL of dichloromethane, and HOBt 54.05mg (0.4mmol), EDC76.68mg (0.4mmol) and 100. mu.L DIEA (0.6mmol) were added and reacted at 30 ℃ for 2 hours. After monitoring the reaction completion, 1N HCl and saturated NaHCO were added respectively3And (4) washing, drying and removing the solvent. Using thin layer chromatographyPlate separation, mobile phase dichloromethane: the eluent with Rf of 0.4-0.6 was collected with methanol 24:1 to give compound (VII). The LC-MS spectrum of compound (VII) is shown in FIG. 7, C69H87N9O12S[M+H]1267.62,found 1267.49.
(4) The resulting compound (VII) was added with 95% TFA and 5% ddH2And reacting for 2 hours to remove all protective groups, and pouring into the ethyl acetate to separate out a white solid (VIII). The LC-MS spectrum of compound (VIII) is shown in FIG. 8, C47H55N9O7[M+H]858.42,found 858.93.
Example 3: fluorescence detection of AIE fluorescent probes
(1) Detection of fluorescence properties in different solvents:
the pipette gun pipetted 10. mu.L of the compound (VIII) DMSO stock solution (4mM) to 990. mu.L of PBS solution (pH7.2, 50mmol/L) and 990. mu.L of DMSO solution, respectively, at a probe concentration of 40. mu.M each. Fluorescence values were measured at 37 ℃ using a microplate reader, respectively, with an excitation wavelength of 340nm and an emission wavelength of 460nm, and the fluorescence spectra are shown in FIG. 9.
Experiments have shown that compound (VIII) (40. mu.M) has a much lower fluorescence intensity in DMSO solutions with good solubility than in PBS solutions with poor solubility, and AIE characteristics due to solubility are evident.
(2) Fluorescence properties at different concentrations were detected:
the pipette was pipetted 10. mu.L of a DMSO solution (8mM) of compound (VIII) into 990. mu.L of PBS (pH7.2, 50mmol/L) at a concentration of 80. mu.M of compound (I) and diluted successively to different concentrations (2. mu.M, 5. mu.M, 10. mu.M, 50. mu.M, 80. mu.M) and the fluorescence was measured at 37 ℃ under excitation at 340 nm. The emission wavelength was 460nm and the fluorescence spectrum is shown in FIG. 10.
Experiments prove that in the PBS solution, under the condition that the emission wavelength is 460nm, the fluorescence difference changes obviously along with the gradual increase of the concentration of the fluorescent compound (VIII), the fluorescence intensity at the concentration of 80 mu M exceeds 100 times of the fluorescence intensity at the concentration of 2 mu M, and the AIE sensitive fluorescence response and the low fluorescence background value are shown.
Claims (7)
1. A phenylalanine derivative with aggregation-induced emission property has a structure shown in formula (I):
2. a method for producing the phenylalanine derivative according to claim 1, which comprises:
(1) protecting 4-iodine-D-phenylalanine amino by using Boc anhydride to obtain a compound (II);
(2) the compound (II) and the diboron pinacol ester are subjected to PdCl in a DMF solvent at 70-80 ℃ under the protection of nitrogen2(dppf) is used as a catalyst, the suzuki reaction is carried out in the presence of KOAc, and the compound (III) is obtained by separation and purification after the reaction is finished;
(3) compound (III) with triphenylbromoethylene in THF and H2In an O mixed solvent, Pd (pph3)4 is used as a catalyst under the protection of nitrogen at 70-80 ℃, and K is added2CO3Carrying out a suzuki reaction in the presence of the compound (IV), and separating and purifying after the reaction is finished to obtain a compound (IV);
(4) removing Boc protecting group from compound (IV) to obtain compound (I);
3. the method according to claim 2, wherein in the step (2), the compound (II), pinacol diboron, PdCl2The ratio of the amounts of substances of (dppf) and KOAc was 1:1.5:0.06: 2.8.
4. The method according to claim 2, wherein in the step (2), the separation and purification method is column chromatography, and the separation and purification method is carried out by using dichloromethane: and (3) taking a mixed solution with the volume ratio of the A being 30:1 as an eluent, collecting a target component, and drying to obtain the compound of the formula (III).
5. The process according to claim 2, wherein in step (3), the compound (III), triphenylbromoethylene, Pd (pph)3)4、K2CO3The amount of substance(s) is 1:1.2:0.05: 3; THF H in solvent2The volume ratio of O is 10: 1.
6. The method according to claim 2, wherein in the step (3), the separation and purification method is column chromatography, and the separation and purification method is carried out by using dichloromethane: and (3) taking mixed liquor with the volume ratio of A to A of 15:1 as eluent, collecting target components, and drying to obtain the compound of the formula (IV).
7. Use of the phenylalanine derivative according to claim 1 for producing an AIE fluorescent probe.
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| CN116041225A (en) * | 2023-03-15 | 2023-05-02 | 杭州思诺达医药科技有限责任公司 | AIE fluorescent compound targeted by prostate specific membrane antigen and preparation method thereof |
| WO2023092715A1 (en) * | 2021-11-23 | 2023-06-01 | 深圳先进技术研究院 | Alanine aggregation-induced emission fluorescent probe, and synthesis method therefor and use thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2023092715A1 (en) * | 2021-11-23 | 2023-06-01 | 深圳先进技术研究院 | Alanine aggregation-induced emission fluorescent probe, and synthesis method therefor and use thereof |
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| CN116041225A (en) * | 2023-03-15 | 2023-05-02 | 杭州思诺达医药科技有限责任公司 | AIE fluorescent compound targeted by prostate specific membrane antigen and preparation method thereof |
| CN116041225B (en) * | 2023-03-15 | 2024-03-29 | 杭州思诺达医药科技有限责任公司 | AIE fluorescent compound targeted by prostate specific membrane antigen and preparation method thereof |
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