CN103073538A - Application of 1,4-dihydropyridine derivative as NO fluorescent probe - Google Patents
Application of 1,4-dihydropyridine derivative as NO fluorescent probe Download PDFInfo
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- CN103073538A CN103073538A CN2012105927819A CN201210592781A CN103073538A CN 103073538 A CN103073538 A CN 103073538A CN 2012105927819 A CN2012105927819 A CN 2012105927819A CN 201210592781 A CN201210592781 A CN 201210592781A CN 103073538 A CN103073538 A CN 103073538A
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Abstract
The invention relates to the field of probes, in particular to an application of a 1,4-dihydropyridine derivative as a NO fluorescent probe. According to the invention, based on the specific effect of the 1,4-dihydropyridine derivative and nitric oxide, (aromatization, resulting in the changes of electronic structure distribution and molecular conformation in the probes) features of corresponding pyridine derivatives are produced, to realize the response of the fluorescent probe to nitric oxide. Based on the changes of the fluorescence in nature before and after the detection (changes in fluorescence emission intensity, fluorescence emission wavelength, fluorescence emission service life and the like), the detection for the nitric oxide is realized.
Description
Technical field
The present invention relates to the molecular probe field, particularly, relate to Isosorbide-5-Nitrae-dihydrogen pyridine derivative as the purposes of NO fluorescent probe.
Background technology
Nitric oxide molecule (NO) has participated in regulating and control the physiological function of a plurality of systems as a kind of important messenger molecule and neuromodulator in the organism.Existing evidence show nitrogen protoxide also with various diseases, relevant such as diabetes, parkinsonism and Alzheimer's disease etc.Therefore the NO donor medicine has caused widely and has paid close attention to as potential cardiovascular, antitumor, novel anti-inflammatory and anti-alzheimer medicine.Yet NO is extremely unstable in vivo as the gas free radical, and the method that therefore detects in vivo NO is one focus, difficult point of correlative study always.
" fluorescent probe " generally refers to can optionally interact with other predetermined substance and its structure is changed, the compound that causes its photoluminescent property (character such as intensity, excitation/emission wavelength or fluorescence lifetime) to change namely under certain condition can be to the compound of predetermined substance generation specificity fluorescent response.Utilize this character, can carry out qualitative, quantitative research to predetermined substance by fluorescence detection method.A class NO fluorescent molecular probe O-Phenylene Diamine class that is most widely used at present, receives much concern, owing to be subjected to the restriction of self structure characteristics and the mechanism of action, still exist and manyly be subjected to the impact of medium pH, the existence of autoxidation phenomenon such as sensitivity, the problems such as specificity is high not are restricted its use.
" Isosorbide-5-Nitrae-dihydrogen pyridine derivative " proposed by the invention can be realized optionally interacting with nitrogen protoxide, and recurring structure changes (aromizing of molecular structure), thereby causes its photoluminescent property to change (for example fluorescent emission intensity enhancing).
Summary of the invention
The purpose of this invention is to provide Isosorbide-5-Nitrae-dihydrogen pyridine derivative as the purposes of NO fluorescent probe.
In order fundamentally to address the above problem, the present invention " switch " unit take Isosorbide-5-Nitrae-dihydrogen pyridine derivative as fluorescent probe makes corresponding fluorescent probe by introducing multiple luminescent dye molecule to No. 4 positions of Isosorbide-5-Nitrae-dihydropyridine ring.According to technical scheme of the present invention, wherein, its structure of Isosorbide-5-Nitrae-dihydrogen pyridine derivative is as with shown in the following formula I:
R
1=-CO
2Et or F, Cl, Br, CN
R
2=luminescent dye molecule
R
3=H or Bn, Ph, Me, Et, Pr, i-Pr, CN
The invention provides Isosorbide-5-Nitrae-dihydrogen pyridine derivative as the purposes of NO fluorescent probe, wherein, introduce multiple luminescent dye molecule to No. 4 positions of Isosorbide-5-Nitrae-dihydropyridine ring, described luminescent dye molecule can for:
According to technical scheme of the present invention, utilize 1,4-dihydrogen pyridine derivative and nitric oxide production specific effect (aromizing, cause the structure distribution of electronics in the probe molecule, the conformational change of molecule etc.), generate the spread out character of class biology of corresponding pyridine, realize that fluorescent probe is to nitric oxide production response.Change (fluorescent emission intensity variation, fluorescent emission wavelength change, fluorescent emission lifetime change etc.) by photoluminescent property before and after the detection effect realizes nitric oxide production detection.
Give an example according to the specific embodiment of the present invention, described Isosorbide-5-Nitrae-dihydrogen pyridine derivative is coumarins and derivative thereof, and the NO probe is that structural formula is suc as formula 1e in this example.And 1c, 1d are the coumarins fluorescent agent, and they are actually the precursor of NO probe 1e, structurally have certain common ground with 1e, and 1f is the product that generates after NO probe 1e and the NO effect, is the coumarins fluorescent agent with extremely strong fluorescence.
Its synthetic route is:
Description of drawings
Fig. 1, a shows the ultra-violet absorption spectrum of 4-methylcoumarin 1c, b shows 4-methylcoumarin 1c fluorescence spectrum.
Fig. 2, a show the ultra-violet absorption spectrum of 4-aldehyde radical coumarin 1 d, and b shows the fluorescence spectrum of 4-aldehyde radical coumarin 1 d.
Fig. 3, a are based on the ultra-violet absorption spectrum of the nitric oxide fluorescent probe (1e) of fluorescent coumarin dye molecule, and b shows the fluorescence spectrum before 1e and the NO effect.
Fig. 4, a shows the nitric oxide fluorescent probe of fluorescent coumarin dye molecule and the ultra-violet absorption spectrum of the product behind the Effect of Nitric Oxide (1f), the fluorescence spectrum of b demonstration effect product (1f).
Fig. 5, a show that fluorescent probe (1e, solid line) and the ultra-violet absorption spectrum of Effect of Nitric Oxide product (1f, dotted line) contrast, and b shows the fluorescence spectrum contrast of fluorescent probe (1e solid line) and NO effect product (1f, dotted line).
Embodiment
Resorcino among the following embodiment, 9-aldehyde radical anthracene, tonka bean camphor all are purchased from Beijing reagent company, and reagent all is purchased from the Beijing Chemical Plant.
Embodiment 1 is synthetic based on the coumarin derivatives of Hantzsch fat synthesis method
1, synthetic (7-hydroxy-4-methyl-2H-chromen-2-one) of 1b
With 11g(100mmol) Resorcino, 13mL (100mmol) methyl aceto acetate, 52mL H
3PO
4Add in the round-bottomed flask, stir 12h under the room temperature, solution becomes yellowly paste is poured yellow paste in the large water gaging into, and suction filtration gets Off-white solid.Get pure white solid with recrystallization from ethyl acetate/petroleum ether.
1H?NMR(400Hz?CDCl
3)δppm:10.50(s,1H),7.60(d,1H,J=8.7Hz),6.82(q,1H,J=2.3Hz),6.70(d,1H,J=2.3Hz),6.12(d,1H,J=0.9Hz),2.36(d,3H,J=0.9Hz).
2, synthetic (the 7-methoxy-4-methyl-2H-chromen-2-one7-methoxyl group-4-methylcoumarin) of 1c
3.5g (22mmol) 1b is dissolved it with 30mL acetone, add 6.03g (43.2mmol) K
2CO
3, stir 10min, add again 3.12g (22mmol) CH
3I, back flow reaction 6h, stopped heating, heat filtering.Filtrate is spin-dried for, gets white solid, ethyl alcohol recrystallization.
1H?NMR(400Hz?CDCl
3)δppm:7.49（d,1H,J=4.8Hz），6.86（q,1H,J=2.5Hz），6.81（d,1H,J=2.4Hz），6.13（d,1H,J=0.9Hz），3.87（s,3H），2.40（d,3H,J=1.0Hz）
3, synthetic (7-methoxy-2-oxo-2H-chromene-4-carbaldehyde) of 1d
With 0.95g(5mmol) 1c, 30mL dimethylbenzene add in the round-bottomed flask, stirs also heating, and it is dissolved gradually.Add again 0.55g(5mmol) SeO
2, behind the back flow reaction 4h, add again 0.55g(5mmol) and SeO
2, continuing back flow reaction 4h, stopped heating recovers room temperature, has yellow solid to separate out, and suction filtration, solid acetonitrile recrystallization obtains yellow needle-like crystal.
1H?NMR(400Hz?CDCl
3)δppm:10.07（s,1H），8.49（d,1H,5.00），6.93（q,1H,2.52），6.86（d,1H,2.48），6.71（s,1H），3.89（s,3H）。
4, synthetic (dimethyl-4-(7-methoxy-2-oxo-2H-chromen-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3, the 5-dicarboxylate) of 1e
In being housed, the 250mL round-bottomed flask of reflux condensing tube, drying tube adds 0.3g (1,47mmol) 1d, 1.07(9.2mmol) methyl acetoacetate, 0.15g (9.2mmol) ammoniacal liquor, 30mL ethanol, stir and back flow reaction 4h, stopped heating, be cooled to room temperature, boil off part ethanol, solution left standstill in ice-water bath, is obtained pure yellow crystals 1e.
1H?NMR(400Hz?CDCl
3)δppm:8.12(d,1H,J=9.08),6.93(d,1H,J=2.5Hz),6.91(d,1H,J=2.5Hz),6.79(d,1H,J=2.5Hz),6.24(s,1H),5.35(s,1H),3.88(s,3H),3.51(s,6H),2.35(s,6H).
5, synthetic (dimethyl-4-(7methoxy-2-oxo-2H-chromen-4-yl)-2,6-dimethylpyridine-3, the 5-dicarboxylate) of 1f
In a little reaction flask, add 0.02g1e, with the dissolving of 1mL methylene dichloride, add excessive nitrite sodium, stir the lower dilute hydrochloric acid that drips gradually, after reaction for some time, solution is used the dichloromethane extraction organic phase, behind the anhydrous sodium sulfate drying again with saturated common salt water washing 3 times, desolventizing obtains pure white solid 1f.
1H?NMR(400Hz?CDCl
3)δppm:6.88(d,1H,J=8.8Hz),6.78(d,1H,J=2.4Hz),6.69(q,1H,J=2.4Hz),6.01(s,1H),3.81(s,3H),3.50(s,6H),2.62(s,6H).
The ultraviolet of embodiment 2, coumarin derivatives and fluorescent probe, photoluminescent property research
1, coumarin derivatives self ultraviolet, photoluminescent property:
As shown in Figure 1, solvent is ethanol, the ultra-violet absorption spectrum of 4-methylcoumarin 1c (Fig. 1 a, c=1.0 * 10
-4MolL
-1, ε=1.81 * 10
4) and 4-methylcoumarin 1c(Fig. 1 b, c=1.0 * 10
-6MolL
-1, λ
Ex=323nm, λ
Em=384nm) fluorescence spectrum.
As shown in Figure 2, ultra-violet absorption spectrum (Fig. 2 a, c=1.0 * 10 of 4-aldehyde radical coumarin 1 d
-4MolL
-1, ε=2.22 * 10
4) and fluorescence spectrum (Fig. 2 b, c=1.0 * 10 of 4-aldehyde radical coumarin 1 d
-6MolL
-1, λ
Ex=324nm, λ
Em=389nm), solvent is ethanol.
As shown in Figure 1 and Figure 2, different substituting group is not remarkable on the photoluminescent property impact of himself on 7-methoxyl group-tonka bean camphor No. 4 positions.
2, based on the nitric oxide fluorescent probe (1e) of fluorescent coumarin dye molecule and with ultraviolet, the photoluminescent property of the product (1f) of Effect of Nitric Oxide:
Be illustrated in figure 3 as ultra-violet absorption spectrum (Fig. 3 a, c=1.0 * 10 based on the nitric oxide fluorescent probe (1e) of fluorescent coumarin dye molecule
-4MolL
-1, ε=2.12 * 10
3), and 1e), and with the NO effect before fluorescence spectrum (c=1.0 * 10
-6MolL
-1, λ
Ex=334nm, λ
Em=411nm), solvent is ethanol.As shown in the figure, to No. 4 positions that Isosorbide-5-Nitrae-dihydropyridine spreads out, (Fig. 3 a) to cause its uv-absorbing reduction by the scion grafting of C-C key for 7-methoxyl group-tonka bean camphor, the fluorescence sharp-decay (almost completely cancellation) (Fig. 3 b) of while luminescent dye molecule, showing as probe molecule does not almost have fluorescence.
Be illustrated in figure 4 as ultra-violet absorption spectrum (Fig. 4 a, c=1.0 * 10 based on nitric oxide fluorescent probe and the product behind the Effect of Nitric Oxide (1f) of fluorescent coumarin dye molecule
-4MolL
-1, ε=1.16 * 10
4); And with fluorescence spectrum (c=1.0 * 10 of NO effect product (1f)
-6MolL
-1, λ
Ex=330nm, λ
Em=427nm), solvent is ethanol.As shown in the figure, behind fluorescent probe (1e) and the Effect of Nitric Oxide, its uv-absorbing obviously strengthens, and the fluorescence of probe molecule sharply increases (increased value〉10 times) (Fig. 3 b) simultaneously.
3, based on the nitric oxide fluorescent probe (1e) of fluorescent coumarin dye molecule and with ultraviolet, the photoluminescent property contrast of Effect of Nitric Oxide product (1f):
Fig. 5 shows the ultra-violet absorption spectrum contrast of fluorescent probe (1e, solid line) and Effect of Nitric Oxide product (1f, dotted line), and (Fig. 5 a), and, fluorescent probe (1e solid line) contrasts (Fig. 5 b) with the fluorescence spectrum of NO effect product (1f, dotted line), and solvent is ethanol.As shown in the figure, behind fluorescent probe (1e) and the Effect of Nitric Oxide, its uv-absorbing obviously strengthens, and the fluorescence of probe molecule sharply increases (increased value〉10 times) (Fig. 3 b) simultaneously.The result of this Experimental Comparison shows 1, the 4-dihydropyridine can be realized specificly-response to nitrogen protoxide, aromizing (being become the pyridine structure of aromaticity by nonaro-maticity dihydropyridine structure) occurs, cause thus the electronic structure of logical fluorescent probe molecule, the variation of distribution, cause the photoluminescent property of probe (cross covalent linkage connect fluorescence dye-Isosorbide-5-Nitrae-dihydropyridine make) to change (from substantially without fluorescence to stronger fluorescence).This principle can be used for the development of new nitric oxide fluorescent probe, to can be used in situ detection, the imaging of cell intracellular nitric oxide, will be to the generation of NO in the organism, conduction and the effect in biological function is regulated thereof, and the research of the aspects such as relevant medical diagnosis on disease, new drug development provides effective research means, detection method.
Claims (3)
1.1 the 4-dihydrogen pyridine derivative is characterized in that as the purposes of NO fluorescent probe the structural formula of described Isosorbide-5-Nitrae-dihydrogen pyridine derivative is as follows:
R
1=-CO
2Et, F, Cl, Br or CN
R
2=luminescent dye molecule
R
3=H, Bn, Ph, Me, Et, Pr, i-Pr or CN.
2. Isosorbide-5-Nitrae-dihydrogen pyridine derivative according to claim 1 is characterized in that as the purposes of NO fluorescent probe, and described luminescent dye molecule is:
3. Isosorbide-5-Nitrae-dihydrogen pyridine derivative according to claim 1 is characterized in that as the purposes of NO fluorescent probe, and the structural formula of described Isosorbide-5-Nitrae-dihydrogen pyridine derivative is as follows:
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Cited By (8)
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| CN103319465A (en) * | 2013-06-25 | 2013-09-25 | 北京师范大学 | Hantzsch ester derivative as well as preparation and application thereof |
| US9383644B2 (en) | 2014-09-18 | 2016-07-05 | Heraeus Precious Metals North America Daychem LLC | Sulfonic acid derivative compounds as photoacid generators in resist applications |
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| CN106317029A (en) * | 2016-08-22 | 2017-01-11 | 山东禾本堂生物科技有限公司 | Dihydropyridine derivative with polyether chains and preparation and application of dihydropyridine derivative |
| CN107056759A (en) * | 2016-06-21 | 2017-08-18 | 北京师范大学 | A kind of new quaternary ammonium salt fluorescence probe and its application |
| CN107353892A (en) * | 2017-07-13 | 2017-11-17 | 长春海谱润斯科技有限公司 | A kind of hot activation delayed fluorescence material and its organic electroluminescence device |
| CN109608427A (en) * | 2018-12-29 | 2019-04-12 | 山东师范大学 | It is a kind of for the two-photon fluorescence probe and its synthetic method of qualitative detection nitric oxide concentration, application |
| CN115181094A (en) * | 2022-08-08 | 2022-10-14 | 南京医科大学 | Pyridine-substituted coumarin derivative, preparation method thereof and application of pyridine-substituted coumarin derivative in preparation of pH fluorescent probe |
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| CN103319465A (en) * | 2013-06-25 | 2013-09-25 | 北京师范大学 | Hantzsch ester derivative as well as preparation and application thereof |
| US9383644B2 (en) | 2014-09-18 | 2016-07-05 | Heraeus Precious Metals North America Daychem LLC | Sulfonic acid derivative compounds as photoacid generators in resist applications |
| US9709886B2 (en) | 2015-03-13 | 2017-07-18 | Heraeus Precious Metals North America Daychem LLC | Sulfonic acid derivative compounds as photoacid generators in resist applications |
| US9477150B2 (en) | 2015-03-13 | 2016-10-25 | Heraeus Precious Metals North America Daychem LLC | Sulfonic acid derivative compounds as photoacid generators in resist applications |
| CN107056759A (en) * | 2016-06-21 | 2017-08-18 | 北京师范大学 | A kind of new quaternary ammonium salt fluorescence probe and its application |
| CN107056759B (en) * | 2016-06-21 | 2021-03-23 | 北京师范大学 | Novel quaternary ammonium salt fluorescent probe and application thereof |
| CN106317029A (en) * | 2016-08-22 | 2017-01-11 | 山东禾本堂生物科技有限公司 | Dihydropyridine derivative with polyether chains and preparation and application of dihydropyridine derivative |
| CN106317029B (en) * | 2016-08-22 | 2018-11-27 | 山东禾本堂生物科技有限公司 | One kind containing polyether chain dihydrogen pyridine derivatives and its preparation and application |
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| CN109608427A (en) * | 2018-12-29 | 2019-04-12 | 山东师范大学 | It is a kind of for the two-photon fluorescence probe and its synthetic method of qualitative detection nitric oxide concentration, application |
| CN115181094A (en) * | 2022-08-08 | 2022-10-14 | 南京医科大学 | Pyridine-substituted coumarin derivative, preparation method thereof and application of pyridine-substituted coumarin derivative in preparation of pH fluorescent probe |
| CN115181094B (en) * | 2022-08-08 | 2024-01-30 | 南京医科大学 | Pyridine-substituted coumarin derivative, preparation method thereof and application of pyridine-substituted coumarin derivative in preparation of pH fluorescent probe |
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