CN102382641A - Fluorescent probe for detecting hypochlorous acid and preparation method thereof - Google Patents
Fluorescent probe for detecting hypochlorous acid and preparation method thereof Download PDFInfo
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- CN102382641A CN102382641A CN201110284516XA CN201110284516A CN102382641A CN 102382641 A CN102382641 A CN 102382641A CN 201110284516X A CN201110284516X A CN 201110284516XA CN 201110284516 A CN201110284516 A CN 201110284516A CN 102382641 A CN102382641 A CN 102382641A
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Abstract
The invention discloses a fluorescent probe for detecting hypochlorous acid and a preparation method thereof, relating to fluorescent probes. The fluorescent probe for detecting hypochlorous acid, which has higher sensitivity and selectivity and is mainly applied to detecting the hypochlorous acid in an aqueous solution under a neutral condition, as well as the preparation method and the application thereof are provided. The fluorescent probe for the detecting hypochlorous acid is a 7-dimethylamino thiomethoxy-3-phenoxazone compound containing a phenoxazone fluorophore structure and taking dimethylamino thioformyl chloride as phenolichydroxyl protective group. The preparation method comprises the following steps of: adding dimethylamino thioformyl chloride to a container, solving the dimethylamino thioformyl chloride by DMF (Dimethyl Formamide), adding resorufin sodium salt and potassium carbonate and stirring to obtain isabelline slurry, diluting the isabelline slurry by a saturated sodium chloride solution to salt out red sediment, drying the red sediment, and separating by a silicagel column to obtain the fluorescent probe for detecting the hypochlorous acid in red powders. The fluorescent probe for detecting the hypochlorous acid can be applied to the fluorescence detection of HC1O in the aqueous solution under the neutral condition.
Description
Technical field
The present invention relates to a kind of fluorescent probe, especially relating to a kind of is hypochlorous fluorescent probe of the detection phenolic hydroxyl group blocking group, that be fluorophore and preparation method thereof Yi the thiophene evil hexazinone with the dimethylin thioformyl.
Background technology
Hypochlorous acid (HClO) is that the organism myeloperoxidase (myeloperoxidase, MPO) play an important role in multiple physiology, pathologic process by a kind of important active oxygen species of mediation generation.Design is synthetic to have high sensitivity, HClO fluorescent probe that specificity is strong; Foundation is applied to the fluorescent microscopic imaging method of HClO in the cell; Realize that target molecule is real-time, the spike of original position; Be molecule relevant in postgraduate's object and cell incident, and the drug screening and the evaluation of relevant disease provide authentic communication with it, have important scientific meaning and application prospect with HClO.This field become people research focus it
In recent years, reported several fluorescent probes to HClO, as DCFH, DHR (referring to document: A.Bizyukin, et al; Bull.Exp.Biol.Med.1995,119,347.), APF (referring to document: T.Nagano, et al; J.Biol.Chem.2003,278,3170.), MitoAR is (referring to document: T.Nagano; Et al, J.Am.Chem.Soc.2007,129; 10324.) etc., but above probe be except can detecting HClO, and other active oxygen species is also had fluorescence response in various degree.Because every kind of active oxygen all has its unique separately physiologically active, therefore the demand to the strong HClO fluorescent probe of specificity seems particularly urgent.In the other HClO probe of having reported, the need that have under the severe condition of strong basicity (like pH 12), use (referring to document: H.M.Ma, et al; Chem.Eur.J.2008,14,4719.); Or poorly water-soluble is (referring to document: W.Tan et al, Chem.Eur.J.2009,15; 2305.), can't really be applied in the living things system.At present, it is few to be applied under the neutrallty condition fluorescent probe that HClO detects in the aqueous solution, and need expensive preparation under loaded down with trivial details exacting terms and get (referring to document: T.Nagano, et al, J.Am.Chem.Soc.2007,129,7313.; Document: J.Tae, et al, Org.Lett.2009,11, (4), 859.; Document: E.Weissleder, P.Libby, et al, Chem.Biol.2007,14,1221.).
Summary of the invention
The objective of the invention is to existing existing deficiency of various HClO fluorescent probes and defective; Provide a kind of sensitivity and selectivity higher, be mainly used in and detect under the neutrallty condition hypochlorous fluorescent probe of hypochlorous detection and preparation method thereof in the aqueous solution.
Another object of the present invention is to provide the application of the hypochlorous fluorescent probe of said detection in the imaging of cell endogenous HClO microscopic fluorescence.
The molecular structural formula of the hypochlorous fluorescent probe of said detection is following:
The hypochlorous fluorescent probe of said detection be contain thiophene evil hexazinone fluorophore structure, be the 7-dimethylin sulfo-formicester base-3-thiophene evil hexazinone compound of phenolic hydroxyl group protection base with the dimethylin thioformyl.
The preparation route of the hypochlorous fluorescent probe of said detection is as follows:
The concrete steps of its preparation method are:
In container, add dimethylin sulfo-formyl chloride, after the DMF dissolving, stir behind adding 7-hydroxyl thiophene evil hexazinone sodium salt and the salt of wormwood; The isabelline soup compound of gained dilutes with saturated nacl aqueous solution; Salt out red precipitate, after the drying, separate with silicagel column; Must detect hypochlorous fluorescent probe, the title product powder that takes on a red color.
Said dimethylin sulfo-formyl chloride: 7-hydroxyl thiophene evil hexazinone sodium salt: salt of wormwood can be 4: 1 by mass ratio: (1～1.5); Said stirring can be stirred 30h under nitrogen atmosphere; Said drying can adopt vacuum-drying; Said silicagel column separates, and can adopt CH
2Cl
2Make eluent.
The hypochlorous fluorescent probe of said detection can be applicable to the fluoroscopic examination of HClO in the aqueous solution under the neutrallty condition.
Detection HClO method proposed by the invention depends on following chemical reaction mechanism: with the blocking group of dimethylin thioformyl as hyperfluorescence property fluorophore 7-hydroxyl-3-thiophene evil hexazinone molecule; The compound that is obtained promptly detects hypochlorous fluorescent probe, detects hypochlorous fluorescent probe and does not have fluorescence.Detect hypochlorous fluorescent probe under the HClO effect; Slough (the going protection) of dimethylin thioformyl blocking group taken place; Again discharge fluorophore 7-hydroxyl-3-thiophene evil hexazinone molecule, realize the rapid variation of the signal of fluorescence from " nothing " to " having " with hyperfluorescence character.Reaction process is as follows:
Its middle probe
1Be the hypochlorous fluorescent probe of detection according to the invention.
Compared with prior art, the invention has the beneficial effects as follows:
Is the fluorescent probe molecule that the phenolic hydroxyl group blocking group designs based on novelty with the dimethylin thioformyl;
No fluorescence of such probe self or fluorescent signal very a little less than, significantly strengthen with HClO effect back fluorescence, so detection is highly sensitive;
Such probe is strong for the specificity of HClO effect;
Such probe self has that chemical property is stable, no autooxidation, with target compound effect unglazed bleaching phenomenon rapidly and after the effect;
Synthetic route is simple.
Therefore, the invention provides a kind of HClO optical probe of excellent performance, the hypochlorous acid biological behaviour provides reliable and practical instrument in the cell in order further to study.
Description of drawings
The fluorescence spectrum of Fig. 1 after for the HClO effect that detects hypochlorous fluorescent probe and different concns.In Fig. 1, X-coordinate is wavelength (nm), and ordinate zou is a relative intensity of fluorescence; In the pH of 0.10mol/L 7.4 phosphate buffer solutions (methyl-sulphoxide/water=1/99, the ratio of volume), detect hypochlorous fluorescent probe concentration and be 1.0 * 10
-5Mol/L, (from bottom to top) NaClO* concentration is respectively: 0,0.1,0.3,0.5,0.7,0.9,2.0,3.0,4.0,5.0,6.0,7.0,9.0,10.0 μ mol/L; Excitation wavelength: 530nm.
* annotate: NaClO is that spontaneous generation acid moves and produce HclO in the aqueous solution under neutrallty condition, and remainder together.
Fig. 2 is for detecting hypochlorous fluorescent probe in the pH of 0.10mol/L 7.4 phosphate buffer solutions (methyl-sulphoxide/water=1/99; The ratio of volume) in; Fluorescence spectrum under acting on respectively for various active oxygen species; Detect hypochlorous fluorescent probe concentration and be 10 μ mol/L, NaClO concentration is 10.0 μ mol/L, and other activity keto concentration is 100.0 μ mol/L; Other active oxygen comprises: H
2O
2,
1O
2, NO, O
2 -, ONOO
-, OH; Excitation wavelength: 550nm.In Fig. 2, X-coordinate is wavelength (nm), and ordinate zou is a relative intensity of fluorescence.
Fig. 3 is for detecting the working curve diagram that hypochlorous fluorescent probe fluorescent method in the aqueous solution of pH7.4 detects NaClO.In Fig. 3, X-coordinate is a NaClO concentration, and ordinate zou is a relative intensity of fluorescence.
Fig. 4 is for detecting the microscopic fluorescence image that hypochlorous fluorescent probe is applied to hypochlorous acid molecule in people's neutrophilic granulocyte.In Fig. 4, detecting hypochlorous fluorescent probe concentration is 10.0 μ mol/L; Figure A, C, E are respectively the confocal fluorescent image that coexists when hypochlorous acid scavenging agent PABA (para amidocyanogen benzoic Acid) is arranged, and the concentration of PABA is respectively 0,8,200 μ mol/L; Figure B, D, F are respectively the stacking diagrams of A, C, E light field figure corresponding with it; Cell concn is 5 * 10
5Individual/mL; Scale is 5 μ m.
Embodiment
Following examples will combine accompanying drawing that the present invention is described further, but the present invention is not limited by the strictness of the following example.
Embodiment 1: the preparation method who detects hypochlorous fluorescent probe
In the 25mL round-bottomed flask, and adding dimethylin sulfo-formyl chloride (1.26g, 10.0mmol); With after the 6.0mL exsiccant DMF dissolving, add respectively 7-hydroxyl thiophene evil hexazinone sodium salt (0.6g, 2.5mmol) and salt of wormwood (0.52g; 3.8mmol), stirring at room 30h under nitrogen atmosphere.The isabelline soup compound of gained salts out red precipitate with the dilution of 350～400mL saturated nacl aqueous solution.After the vacuum-drying, separate (CH with silicagel column
2Cl
2Make eluent), get red powder (title product promptly detects hypochlorous fluorescent probe) 0.375g.(productive rate 50%).
ESI-MS：C
15H
12N
2O
3S，m/z：301.1(M+1)
+。
1H?NMR(CDCl
3)：δ3.388(s，3H，NCH
3)，3.477(s，3H，NCH
3)，6.331(d，J＝1.2Hz，1H，ArH)，6.866(q，J＝6.0Hz，1H，ArH)，7.093(q，J＝3.4Hz，1H，ArH)，7.120(d，J＝2.4Hz，1H，ArH)，7.442(d，J＝10.0Hz，1H，ArH)，7.808(d，J＝8.4Hz，1H，ArH)。
13C?NMR(CDCl
3)：δ39.04，39.44，107.18，111.25，120.88，130.80，131.42，134.82，135.24，144.21，148.24，149.36，156.61，186.36，189.39。
Embodiment 2: detect the description of hypochlorous fluorescent probe chemical property and in the microscopic fluorescence imaging applications of cell endogenous HClO
One, at the neutral aqueous solution middle probe
1The detection performance test:
(1) preparation steps of test fluid:
In the scale test tube of 10mL; Adding 5.0mL concentration successively is pH 7.40 phosphoric acid buffers of 0.2mol/L; A certain amount of standard NaClO solution (is accurately demarcated with spectrophotometry, referring to document: M.Mazda and D.W.Margerum.Inorg.Chem.1994,33 in advance; 118.), with three distilled water dilutings to scale.Shake up.The concentration that adds 0.1mL is 1.0 * 10
-3The methyl alcohol storing solution of the hypochlorous fluorescent probe of detection of mol/L shakes up.Carry out related assays immediately.As above operation, but do not add the hypochlorous fluorescent probe solution of detection of hypochlorous acid or other active oxygens, be the preparation of blank test solution.
(2) spectral response curve of the hypochlorous fluorescent probe of detection in the aqueous solution and detection performance.In conjunction with marginal data.
Fig. 1 be detect hypochlorous fluorescent probe in neutral aqueous solution to hypochlorous fluorescence response.Fig. 1 shows, detects originally (the λ em >=500nm) almost do not have fluorescence, in the presence of NaClO in the visible wavelength district of hypochlorous fluorescent probe; The fluorescence of system significantly strengthens; Its maximum emission wavelength is positioned at 581nm, and along with the continuous adding of NaClO, system fluorescence constantly strengthens.This phenomenon shows, detects that hypochlorous fluorescent probe has sensitivity to hypochlorous acid and fluorescent signal response rapidly.
Fig. 2 detects the fluorescence response spectrogram that hypochlorous fluorescent probe acts on respectively various active oxygen species.Curve 1 is for only detecting the fluorescence spectrum figure under the hypochlorous fluorescent probe existence; Curve 2 is normal 10 for detecting hypochlorous fluorescent probe
1O
2, H
2O
2, OH, ONOO
-Fluorescence spectrum under existing respectively; Curve 3,4 is for detecting hypochlorous fluorescent probe at 10 normal NO, O
2 -Fluorescence spectrum under existing respectively, curve 5 is for detecting the fluorescence spectrum of hypochlorous fluorescent probe in the presence of 1 normal NaClO.
Fig. 2 shows that the relative intensity of fluorescence of system significantly strengthened under only NaClO existed.By contrast, concentration is 10 times of normal other common active oxygen species (H of NaClO
2O
2,
1O
2, NO, ONOO
-, when OH) distinguishing exist singly, detect hypochlorous fluorescent probe and all produce tangible fluorescent signal hardly.This phenomenon shows, detects hypochlorous fluorescent probe has high selectivity to target compound NaClO fluorescence response.
Fig. 3 is for detecting hypochlorous fluorescent probe detects NaClO in the aqueous solution of pH7.4 working curve diagram.Result of study shows that the fluorescence intensity of system is 0.02 * 10
-6Mol/L～35 * 10
-6Present good linear relationship with NaClO concentration in the concentration range of mol/L.
Two, detect hypochlorous fluorescent probe and be applied to the hypochlorous microscopic fluorescence imaging of endogenous in the cell
(1) pre-treatment of cell: healthy volunteer's anti-freezing blood number milliliter, with neutrophil leucocyte parting liquid gradient densimetry separate neutrophil leucocyte.Phosphate buffer solution adjustment cell concn 5 * 10 with pH7.4
5Individual/mL.In 9 Tissue Culture Dishs, move into 0.5mL enchylema respectively, divide 3 groups, every group 3 ware.The 1st group of each ware adds the 0.5mL phosphoric acid buffer respectively; 2nd, 3 groups of corresponding 0.5mL 8.0 * 10 that add respectively of each ware
-6Mol/L, 2.0 * 10
-4The mol/L para amidocyanogen benzoic Acid (PABA, the scavenging agent of HClO: referring to document Z.W.She, et al.Free Redic.Biol.Med.1997,22 (6), 989-998.).Inhibition time 120min, probe load time 45min.The fluorescence focal imaging excites with 514nm.
(2) the detection performance test of HClO in the hypochlorous fluorescent probe pair cell of detection
Detect hypochlorous fluorescent probe the fluorescence co-focusing micro-imaging result of HClO in the human peripheral neutrophil leucocyte is seen Fig. 4.Visible by figure A, detect hypochlorous fluorescent probe and in neutrophil leucocyte, produce bright fluorescence.And visible by figure B, C, the adding in advance of HClO suppressor factor PABA makes fluorescent weakening in the cell, and along with the increase of suppressor factor PABA concentration, fluorescence presents reducing tendency gradually.This result show probe not only can pair cell in endogenous HClO realize the sensitive fluorescence imaging, and have good selectivity.
Claims (7)
1. detect hypochlorous fluorescent probe, it is characterized in that its molecular structural formula is following:
The hypochlorous fluorescent probe of said detection be contain thiophene evil hexazinone fluorophore structure, be the 7-dimethylin sulfo-formicester base-3-thiophene evil hexazinone compound of phenolic hydroxyl group protection base with the dimethylin thioformyl.
2. the preparation method of the hypochlorous fluorescent probe of detection as claimed in claim 1 is characterized in that its concrete steps are:
In container, add dimethylin sulfo-formyl chloride, after the DMF dissolving, stir behind adding 7-hydroxyl thiophene evil hexazinone sodium salt and the salt of wormwood; The isabelline soup compound of gained dilutes with saturated nacl aqueous solution; Salt out red precipitate, after the drying, separate with silicagel column; Must detect hypochlorous fluorescent probe, the title product powder that takes on a red color.
3. the preparation method of the hypochlorous fluorescent probe of detection as claimed in claim 2 is characterized in that said dimethylin sulfo-formyl chloride: 7-hydroxyl thiophene evil hexazinone sodium salt: salt of wormwood is 4: 1 by mass ratio: (1～1.5).
4. the preparation method of the hypochlorous fluorescent probe of detection as claimed in claim 2 is characterized in that said stirring is under nitrogen atmosphere, to stir 30h.
5. the preparation method of the hypochlorous fluorescent probe of detection as claimed in claim 2 is characterized in that said drying is to adopt vacuum-drying.
6. the preparation method of the hypochlorous fluorescent probe of detection as claimed in claim 2 is characterized in that said silicagel column separates, and is to adopt CH
2Cl
2Make eluent.
7. be applied to the fluoroscopic examination of HClO in the aqueous solution under the neutrallty condition like the hypochlorous fluorescent probe of the said detection of right claim 1.
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Cited By (13)
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| CN103436254A (en) * | 2013-08-19 | 2013-12-11 | 中国科学院合肥物质科学研究院 | Functional multi-nitrogen heterocyclic ring fluorescent probe, preparation method and application thereof |
| CN103604783A (en) * | 2013-11-01 | 2014-02-26 | 大连理工大学 | Method for reversible detection on hypochlorite and hydrogen sulfide |
| CN103848787A (en) * | 2012-12-06 | 2014-06-11 | 中国科学院大连化学物理研究所 | Fluorescence probe and application thereof in reversible detection of hypochlorous acid |
| CN103940788A (en) * | 2013-01-17 | 2014-07-23 | 华东理工大学 | Application of nano silver cluster in detection of hypochloric acid content, and detection method |
| CN105319192A (en) * | 2015-11-12 | 2016-02-10 | 湖南科技大学 | Method for detecting hypochlorite anions through water-soluble fluorescent silica nanoparticle |
| CN107253936A (en) * | 2017-06-23 | 2017-10-17 | 复旦大学 | One class can be used for fluorescence probe of hypochlorous acid detection and its preparation method and application |
| CN107266397A (en) * | 2017-06-26 | 2017-10-20 | 闫语 | A kind of preparation and application of thiocarbamates hypochlorous acid fluorescence probe |
| CN107987049A (en) * | 2017-12-07 | 2018-05-04 | 济南大学 | A kind of Fluorescence Increasing type two-photon hypochlorous acid fluorescence probe and its preparation method and application |
| CN108191852A (en) * | 2017-05-04 | 2018-06-22 | 泰山医学院 | One kind is used to detect hypochlorous fluorescence probe and its application |
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| CN113004216A (en) * | 2019-12-20 | 2021-06-22 | 湖南超亟化学科技有限公司 | Preparation method and application of novel benzoxazine hypochlorous acid fluorescent molecular probe |
| CN113004216B (en) * | 2019-12-20 | 2023-10-03 | 湖南超亟检测技术有限责任公司 | Preparation method and application of benzoxazine hypochlorous acid fluorescent molecular probe |
| CN113200935A (en) * | 2021-04-26 | 2021-08-03 | 威海海洋生物医药产业技术研究院有限公司 | Fluorescent probe for hypochlorous acid detection and preparation method thereof |
| CN113200935B (en) * | 2021-04-26 | 2022-07-08 | 威海海洋生物医药产业技术研究院有限公司 | Fluorescent probe for hypochlorous acid detection and preparation method thereof |
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