CN109503615A - A kind of Pseudolarix acid B photoaffinity probe and preparation method thereof - Google Patents
A kind of Pseudolarix acid B photoaffinity probe and preparation method thereof Download PDFInfo
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- 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"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- 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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Abstract
The present invention relates to a kind of Pseudolarix acid B photoaffinity probe and preparation method thereof, its general formula of the chemical structures are as follows:In formula, group Ac is acetyl group.Pseudolarix acid B group is connected on the amido compounds containing alkynyl by design and forms special chemical structure, it can be used to capture, identify corresponding binding protein, and specifically bind progress to it, to determine PAB bacteriostasis target spot.
Description
Technical field
The invention belongs to fluorescence probe fields, are related to a kind of photoaffinity probe, and in particular to a kind of Pseudolarix acid B light parent
With probe and preparation method thereof.
Background technique
Pseudolarix acid B is one of the bark of pinaceae plant golden larch diterpene sour component, it is applied to resist in medicine
Fungi, hemostasis and neurodermatitis etc..Some researches show that Pseudolarix acid B can inhibit revascularization, can be used in the recent period
Prevention or treating cancer, diabetes, psoriasis, hemangioma etc..
Fluorescence probe, which refers to, has characteristic fluorescence, and its photoluminescent property (excitation and transmitting in ultraviolet-visible-near infrared region
Wavelength, intensity, service life, polarization etc.) it can change and delicately change with the property of local environment, such as polarity, refractive index, viscosity
A kind of fluorescence molecule.Currently used fluorescence probe has fluoresceins probe, inorganic ions fluorescence probe, fluorescent quantum
Point, molecular beacon etc.；It is in addition to being applied to the quantitative analysis of nucleic acid and protein, in nucleic acid staining, DNA electrophoresis, nucleic acid molecules
It suffers from and is widely applied on hybridization, quantitative PCR technique and DNA sequencing.Fluorescence probe is most commonly used to fluorescent immune method acceptance of the bid
Remember antigen or antibody, also can be used for microenvironment, as surfactant micellar, bimolecular film, protein active sites etc. are microcosmic
The detection of characteristic；Usually require that the molar absorption coefficient of probe is big, fluorescence quantum yield is high；Fluorescence emission wavelengths be in long wave and
There is biggish Stokes shift；When for immunoassay, and the combination of antigen or antibody should not influence their activity；Obviously
Need fluorescence probe that there is special chemical structure.
Summary of the invention
A kind of Pseudolarix acid B photoaffinity probe is provided the invention aims to overcome the deficiencies in the prior art.
In order to achieve the above objectives, the technical solution adopted by the present invention is that: a kind of Pseudolarix acid B photoaffinity probe, its change
Learn general structure are as follows:
In formula, group Ac is acetyl group.
Another object of the present invention is to provide a kind of preparation method of above-mentioned Pseudolarix acid B photoaffinity probe, it includes
Following steps:
(a) diisopropylamine, THF are added into reaction vessel, is cooled to 0 DEG C or less under nitrogen protection；It is added dropwise just
Butyl lithium continues that ethyl acetoacetate is added dropwise after stirring, allyl bromide, bromoallylene is added dropwise after stirring again；It is warmed to room temperature and is stirred after dripping off
Reaction；It is then poured into saturated ammonium chloride solution, extraction, washing, concentrated column obtain compound 1；
(b) back flow reaction is carried out after mixing the compound 1, p-methyl benzenesulfonic acid, benzene and ethylene glycol；Saturated carbon is used respectively
Sour hydrogen sodium, saturated sodium-chloride washing, concentrated column obtain compound 2；
(c) it is cooled to 0 DEG C after mixing the compound 2 with tetrahydrofuran or hereinafter, LiAlH is added portionwise4, after adding
It is warmed to room temperature and is stirred to react；Water quenching is added to go out, extracts, wash, concentrated column obtains compound 3；
(d) it is stirred to react after mixing the compound 3, acetone, water and p-methyl benzenesulfonic acid, concentrated column obtains chemical combination
Object 4；
(e) under conditions of the dry ice bath, the compound 4 is added in liquefied ammonia and is reacted；Azanol-O- sulphur is then added
The methanol solution of acid, is warming up to room temperature and is stirred to react；It is filtered to remove insoluble matter, methanol and three second are added after filtrate is spin-dried for
The methanol solution of iodine is added dropwise under conditions of ice bath, continues to be stirred to react for amine；Extraction, washing, concentrated column obtain compound 5；
(f) will imidazoles, triphenylphosphine and methylene chloride be added reaction flask in, be cooled to 0 DEG C or hereinafter, be added elemental iodine into
Row reaction；The dichloromethane solution of the compound 5 is then added, is protected from light；Add saturated sodium bisulfite solution to be quenched, extracts
It takes, concentrated column obtains compound 6；
(g) it after mixing the compound 6, sodium azide and DMF, is protected from light；Add water quenching to go out, extracts, is spin-dried for changing
Close object 7；
(h) after mixing the compound 7, triphenylphosphine, tetrahydrofuran and water, it is protected from light containing compound 8
Reaction solution；
(i) it after mixing Pseudolarix acid B, I-hydroxybenzotriazole, EDCI, DIPEA and methylene chloride, is added after reaction
The reaction solution containing compound 8 continues to be protected from light；Water quenching is added to go out, methylene chloride extraction is spin-dried for, crosses column purification.
Due to the above technical solutions, the present invention has the following advantages over the prior art: corter pseudolaricis second of the present invention
Sour photoaffinity probe, it can be used to capture, identify corresponding binding protein, and progress is specifically bound to it, to determine that PAB presses down
Bacterium action target spot.
Detailed description of the invention
Fig. 1 is the synthetic route chart of Pseudolarix acid B photoaffinity probe of the present invention；
Fig. 2 is nuclear magnetic spectrogram-hydrogen spectrum of compound 4；
Fig. 3 is nuclear magnetic spectrogram-hydrogen spectrum of compound 5；
Fig. 4 is nuclear magnetic spectrogram-hydrogen spectrum of compound 6；
Fig. 5 is nuclear magnetic spectrogram-hydrogen spectrum of compound 8；
Fig. 6 is nuclear magnetic spectrogram-carbon spectrum of compound 8.
Specific embodiment
Below in conjunction with figure embodiment, invention is further explained.
Embodiment 1
The present embodiment provides a kind of Pseudolarix acid B photoaffinity probes and preparation method thereof, as shown in Figure 1, it includes following
Step:
(a) add diisopropylamine (187.1g, 1.8494mol), 900mL THF in 2L there-necked flask, drop under nitrogen protection
Temperature is to 0 DEG C (or 0 DEG C or less)；It is added dropwise n-BuLi (740mL, 1.8494mol), stirs 30min after dripping off；Continue that second is added dropwise
Ethyl acetoacetic acid ethyl ester (109.4g, 0.8406mol), stirs 15min after dripping off；Continue be added dropwise allyl bromide, bromoallylene (100g, 0.8406
Mol), 0 DEG C of temperature control is warmed to room temperature stirring 3h, raw material fully reacting hereinafter, dripping off.System is poured into saturated ammonium chloride solution,
It is extracted twice with EA, merges organic phase；Saturated sodium-chloride washing, concentrated column obtain yellow oil 80g compound 1, yield:
57%；
(b) 1 (77g, 0.458mol), TsOHH are added into 1L there-necked flask2O (17.6g), benzene (300mL) and ethylene glycol
(284g, 4.578mol), reflux water-dividing；It is stirred to react 6h；TLC detection display raw material fully reacting.It is separately added into unsaturated carbonate
The washing of hydrogen sodium, saturated sodium-chloride washing；Dry concentration, column excessively obtains yellow oily liquid 80g compound 2, yield: 83%；
(c) compound 2 (78g, 0.367mol), THF (780mL) are added into 2L single port bottle, is cooled to 0 DEG C；In batches plus
Enter LiAlH4(20.9g, 0.551mol are divided into 3~4 batches), 0 DEG C of temperature control or so；It adds, is warmed to room temperature stirring, TLC prison naturally
It controls to raw material fully reacting.Water quenching is added to go out, pad diatomite filtering, EA is washed three times；Liquid separation, water phase EA extract primary, conjunction
And organic phase, saturated sodium-chloride washing；Concentrated column obtains yellow oily liquid 55g compound 3, yield 89%.
(d) into 1L single port bottle be added compound 3 (55g, 0.323mol), acetone (550mL), water (55mL) and
TsOH·H2O (6.15g, 0.032mol), TLC are monitored to raw material fully reacting；It crosses column and obtains pale yellow oily liquid 34g chemical combination
Object 4 (its nuclear magnetic spectrogram as shown in Fig. 2, specifically:1H NMR(400MHz,CDCl3)δ(ppm):3.84(t,2H), 5.71-
2.67(m,5H),2.46-2.42(m,2H),1.95(t,1H))；
(e) ammonia is cooled to liquefied ammonia with the dry ice bath (- 40 DEG C), liquefied ammonia is added in compound 4 (5g, 39.7mmol, 1eq)
In, it is reacted 5 hours under conditions of -40 DEG C；The methanol (50 of hydroxylamine-o-sulfonic acid (5.83g, 51.6mmol, 1.3eq) is added
ML) solution warms naturally to room temperature reaction overnight after adding；After contact plate is without raw material, it is filtered to remove insoluble matter, filtrate adds after being spin-dried for
Enter methanol (50ml) and triethylamine (40ml, 293.6mmol, 7.4eq), ice bath be cooled to 0 DEG C of dropwise addition iodine (13g, 51.6mmol,
Methanol (50ml) solution 1.3eq), natural temperature reaction 4 hours.Add saturated salt solution, isopropyl ether extraction, washes, dry, rotation
It is dry, cross column purification and obtain product 1.0g compound 5, yield: 18.2% (its nuclear magnetic spectrogram as shown in figure 3, specifically:1H NMR
(400MHz,CDCl3)δ(ppm):3.51(t,2H),2.08-2.01(m,3H),1.74-1.69(m,4H))；
(f) by imidazoles (740mg, 10.87mmol, 3.0eq), triphenylphosphine (1.05g, 3.99mmol, 1.1eq) and dichloro
Methane (5ml) is added in reaction flask, is cooled to 0 DEG C, is added elemental iodine (1.1g, 4.35mmol, 1.2eq), adds insulation reaction
30 minutes, methylene chloride (1ml) solution of compound 5 (500mg, 3.62mmol, 1eq) is added under low temperature, adds heat preservation and is protected from light
Reaction 4 hours.Saturated sodium bisulfite solution is added to be quenched, ethyl acetate extraction is dry, is spin-dried for, and crosses column purification and obtains product 400mgization
Close object 6, yield: 46% (its nuclear magnetic spectrogram as shown in figure 4, specifically:1H NMR(400MHz, CDCl3)δ(ppm):2.91(t,
2H),2.16-2.03(m,5H),1.71(t,2H))。
(g) by compound 6 (400mg, 1.6mmol, 1.0eq), sodium azide (125mg, 1.92mmol, 1.2eq) and
DMF (4ml) is added in reaction flask, is warming up to 70 DEG C, is protected from light 5 hours；Water quenching is added to go out, ethyl acetate extraction, dry, rotation
It is dry, obtain crude product 200mg compound 7, yield: 76%.
(h) by compound 7 (150mg, 0.92mmol, 1.0eq), triphenylphosphine (278mg, 1.06mmol, 1.15eq), four
Hydrogen furans (3ml) and water (0.3ml) are added in reaction flask, and reacting at normal temperature without light 15 hours, contact plate discovery must contain change without raw material
The reaction solution for closing object 8 remains in next step；
(i) by Pseudolarix acid B (200mg, 0.46mmol, 1.0eq), HOBT (162mg, 1.2mmol, 2.6eq), EDCI
Reaction flask is added in (142mg, 0.74mmol, 1.6eq), DIPEA (143mg, 1.11mmol, 2.4eq) and methylene chloride (10ml)
In, normal-temperature reaction 1 hour, the reaction solution of compound 8 is added, adds reacting at normal temperature without light 4 hours；Water quenching is added to go out, methylene chloride
Extraction, it is dry, it is spin-dried for, crosses column purification and obtain product 220mg PAB- probe compound (i.e. Pseudolarix acid B photoaffinity probe chemical combination
Object), two step yields: 44% (step h and step i), nuclear magnetic spectrogram is as shown in Figure 5 and Figure 6, specifically:1H NMR
(400MHz, CDCl3) δ 7.26-7.20 (m, 1H), 6.96 (d, J=11.4Hz, 1H), 6.51 (dd, J=15.0,11.3Hz,
1H), 5.83 (d, J=15.0Hz, 1H), 3.72 (s, 3H), 3.29 (d, J=5.4Hz, 1H), 3.20 (q, J=6.4 Hz, 2H),
3.08 (dd, J=14.3,6.4Hz, 1H), 2.89 (dd, J=15.6,6.3Hz, 1H), 2.75 (dd, J=15.1,8.8Hz,
1H), 2.64-2.58 (m, 1H), 2.19-2.10 (m, 4H), 2.04 (dd, J=7.2,2.6Hz, 2H), 1.99 (s, 3H), 1.85-
1.71 (m, 7H), 1.66 (t, J=7.1Hz, 3H) .ESI calcd.for C30H38N3O7[M+H]+:552.2；Found:
552.2704
Embodiment 2
The present embodiment provides a kind of Pseudolarix acid B photoaffinity probe and preparation method thereof, it with it is basic in embodiment 1
Unanimously, unlike: in step (i), the additional amount of Pseudolarix acid B is 1.5eq, and final column purification of crossing obtains product 280mg
PAB- probe compound.
Embodiment 3
The present embodiment provides a kind of Pseudolarix acid B photoaffinity probe and preparation method thereof, it with it is basic in embodiment 1
Unanimously, unlike: in step (i), the additional amount of Pseudolarix acid B is 0.8eq, and final column purification of crossing obtains product 160mg
PAB- probe compound.
The above embodiments merely illustrate the technical concept and features of the present invention, and its object is to allow person skilled in the art
Scholar cans understand the content of the present invention and implement it accordingly, and it is not intended to limit the scope of the present invention, it is all according to the present invention
Equivalent change or modification made by Spirit Essence, should be covered by the protection scope of the present invention.
Claims (2)
1. a kind of Pseudolarix acid B photoaffinity probe, which is characterized in that its general formula of the chemical structure are as follows:
In formula, group Ac is acetyl group.
2. the preparation method of Pseudolarix acid B photoaffinity probe described in claim 1, which is characterized in that it the following steps are included:
(a) diisopropylamine, THF are added into reaction vessel, is cooled to 0 DEG C or less under nitrogen protection；Normal-butyl is added dropwise
Lithium continues that ethyl acetoacetate is added dropwise after stirring, allyl bromide, bromoallylene is added dropwise after stirring again；It is warmed to room temperature and is stirred instead after dripping off
It answers；It is then poured into saturated ammonium chloride solution, extraction, washing, concentrated column obtain compound 1；
(b) back flow reaction is carried out after mixing the compound 1, p-methyl benzenesulfonic acid, benzene and ethylene glycol；Unsaturated carbonate hydrogen is used respectively
Sodium, saturated sodium-chloride washing, concentrated column obtain compound 2；
(c) it is cooled to 0 DEG C after mixing the compound 2 with tetrahydrofuran or hereinafter, LiAlH is added portionwise4, risen to after adding
Room temperature is stirred to react；Water quenching is added to go out, extracts, wash, concentrated column obtains compound 3；
(d) it is stirred to react after mixing the compound 3, acetone, water and p-methyl benzenesulfonic acid, concentrated column obtains compound 4；
(e) under conditions of the dry ice bath, the compound 4 is added in liquefied ammonia and is reacted；Hydroxylamine-o-sulfonic acid is then added
Methanol solution is warming up to room temperature and is stirred to react；It is filtered to remove insoluble matter, methanol and triethylamine are added after filtrate is spin-dried for,
The methanol solution of iodine is added dropwise under conditions of ice bath, continues to be stirred to react；Extraction, washing, concentrated column obtain compound 5；
(f) imidazoles, triphenylphosphine and methylene chloride are added in reaction flask, are cooled to 0 DEG C or are carried out instead hereinafter, elemental iodine is added
It answers；The dichloromethane solution of the compound 5 is then added, is protected from light；Add saturated sodium bisulfite solution to be quenched, extracts, is dense
The column that contracted obtains compound 6；
(g) it after mixing the compound 6, sodium azide and DMF, is protected from light；Add water quenching to go out, extracts, is spin-dried for obtaining compound
7；
(h) after mixing the compound 7, triphenylphosphine, tetrahydrofuran and water, it is protected from light to obtain the reaction containing compound 8
Liquid；
(i) described in being added after mixing Pseudolarix acid B, I-hydroxybenzotriazole, EDCI, DIPEA and methylene chloride, after reaction
Reaction solution containing compound 8 continues to be protected from light；Water quenching is added to go out, methylene chloride extraction is spin-dried for, crosses column purification.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003018591A1 (en) * | 2001-08-14 | 2003-03-06 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Novel pseudolaric acid-b derivatives, their preparation and pharmaceutical compositions |
| CN102219772A (en) * | 2011-06-20 | 2011-10-19 | 东莞广州中医药大学中医药数理工程研究院 | Cortex pseudolaricis acid complex with bioactivity and preparation method thereof |
| CN102408403A (en) * | 2011-09-26 | 2012-04-11 | 宋云龙 | Pseudolaric acid derivatives, and preparation method and application thereof |
| US20120303057A1 (en) * | 2011-05-24 | 2012-11-29 | Young Bin Choy | Suture Comprising Drug-Loaded Polymer Layer and Method of Manufacturing the Same |
-
2018
- 2018-11-02 CN CN201811299239.8A patent/CN109503615A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003018591A1 (en) * | 2001-08-14 | 2003-03-06 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Novel pseudolaric acid-b derivatives, their preparation and pharmaceutical compositions |
| US20120303057A1 (en) * | 2011-05-24 | 2012-11-29 | Young Bin Choy | Suture Comprising Drug-Loaded Polymer Layer and Method of Manufacturing the Same |
| CN102219772A (en) * | 2011-06-20 | 2011-10-19 | 东莞广州中医药大学中医药数理工程研究院 | Cortex pseudolaricis acid complex with bioactivity and preparation method thereof |
| CN102408403A (en) * | 2011-09-26 | 2012-04-11 | 宋云龙 | Pseudolaric acid derivatives, and preparation method and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| KENJI HAYAKAWA ET AL.: "Novel Bicycloannulation via Tandem Vinylation and Intramolecular Diels-Alder Reaction of Five-Membered Heterocycles: A New Approach to Construction of Psoralen and Azapsoralen", 《J. AM. CHEM. SOC.》 * |
| YIQING ZHOU ET AL.: "Chemical proteomics reveal CD147 as a functional target of pseudolaric acid B in human cancer cells", 《CHEM. COMMUN.》 * |
| YUSHENG XIE ET AL.: "Fluorescent Probes for Single-Step Detection and Proteomic Profiling of Histone Deacetylases", 《J. AM. CHEM. SOC.》 * |
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Application publication date: 20190322 |