CN102382641B - Fluorescent probe for detecting hypochlorous acid and preparation method thereof - Google Patents

Fluorescent probe for detecting hypochlorous acid and preparation method thereof Download PDF

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CN102382641B
CN102382641B CN201110284516XA CN201110284516A CN102382641B CN 102382641 B CN102382641 B CN 102382641B CN 201110284516X A CN201110284516X A CN 201110284516XA CN 201110284516 A CN201110284516 A CN 201110284516A CN 102382641 B CN102382641 B CN 102382641B
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fluorescent probe
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hypochlorous
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hypochlorous acid
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郑洪�
詹心琪
王淑萍
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Xiamen University
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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

Detect hypochlorous fluorescent probe and preparation method thereof
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 with HClO, and the drug screening of associated disease and evaluation provide authentic communication, has important scientific meaning and application prospect.This field become people research focus it
In recent years, several fluorescent probes have been reported at HClO, as DCFH, DHR (referring to document: A.Bizyukin, et al, Bull.Exp.Biol.Med.1995,119,347.), APF is (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 in various degree fluorescence response.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 use under the severe condition of strong basicity (as pH 12) (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 at 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 described detection in the imaging of cell endogenous HClO microscopic fluorescence.
The molecular structural formula of the hypochlorous fluorescent probe of described detection is as follows:
Figure BDA0000093327980000021
The hypochlorous fluorescent probe of described detection be contain thiophene evil hexazinone fluorophore structure, be the 7-dimethylin sulfo-formicester base-3-thiophene evil hexazinone compound of phenolic hydroxyl group protecting group with the dimethylin thioformyl.
The preparation route of the hypochlorous fluorescent probe of described detection is as follows:
Figure BDA0000093327980000022
The concrete steps of its preparation method are:
In container, add dimethylin sulfo-formyl chloride, after the DMF dissolving, stir after adding 7-hydroxyl thiophene evil hexazinone sodium salt and 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 target product powder that takes on a red color.
Described dimethylin sulfo-formyl chloride: 7-hydroxyl thiophene evil hexazinone sodium salt: salt of wormwood can be 4: 1 by mass ratio: (1～1.5); Described stirring can be stirred 30h under nitrogen atmosphere; Described drying can adopt vacuum-drying; Described silicagel column separates, and can adopt CH 2Cl 2Make eluent.
The hypochlorous fluorescent probe of described 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 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:
Figure BDA0000093327980000023
Its middle probe 1Be the hypochlorous fluorescent probe of detection of the present 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 are very weak, 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 base equilibrium 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 the invention will be further described in conjunction with the accompanying drawings, 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 (target 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 in advance, referring to document: M.Mazda and D.W.Margerum.Inorg.Chem.1994,33,118.), 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 Individual existence, 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 with pH7.4 is adjusted cell concn 5 * 10 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 of HClO in the human peripheral neutrophil leucocyte be the results are shown in Figure 4.By figure A as seen, detect hypochlorous fluorescent probe and in neutrophil leucocyte, produce bright fluorescence.And by figure B, C as seen, the adding in advance of HClO inhibitor PABA makes fluorescent weakening in the cell, and along with the increase of inhibitor 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 as follows:
Figure FDA00003173690900011
The hypochlorous fluorescent probe of described detection be contain thiophene evil hexazinone fluorophore structure, be the 7-dimethylin sulfo-formicester base-3-thiophene evil hexazinone compound of phenolic hydroxyl group protecting group 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 after adding 7-hydroxyl thiophene evil hexazinone sodium salt and 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 target 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 described dimethylin sulfo-formyl chloride is 1.26g, and 7-hydroxyl thiophene evil hexazinone sodium salt is 0.6g, and salt of wormwood is 0.52g.
4. the preparation method of the hypochlorous fluorescent probe of detection as claimed in claim 2 is characterized in that described stirring is to stir 30h under nitrogen atmosphere.
5. the preparation method of the hypochlorous fluorescent probe of detection as claimed in claim 2 is characterized in that described 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 described silicagel column separates, and is to adopt CH 2Cl 2Make eluent.
7. detect hypochlorous fluorescent probe according to claim 1 and be applied to the fluoroscopic examination of HClO in the aqueous solution under the neutrallty condition.
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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
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CN107253936B (en) * 2017-06-23 2021-07-23 复旦大学 Fluorescent probe capable of being used for hypochlorous acid detection and preparation method and application thereof
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CN110372632B (en) * 2019-07-26 2021-04-06 广东轻工职业技术学院 Fluorescent probe molecule for rapidly identifying hypochlorite ions and preparation method and application thereof
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