CN107857876A - One kind enhancing fluorescence probe and preparation method thereof - Google Patents

One kind enhancing fluorescence probe and preparation method thereof Download PDF

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CN107857876A
CN107857876A CN201711210236.8A CN201711210236A CN107857876A CN 107857876 A CN107857876 A CN 107857876A CN 201711210236 A CN201711210236 A CN 201711210236A CN 107857876 A CN107857876 A CN 107857876A
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fluorescence probe
peg
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enhancing fluorescence
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倪润炎
王伟
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Suzhou Jindian Biotechnology Co Ltd
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    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
    • C08G65/3344—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing oxygen in addition to sulfur
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    • G01N21/64—Fluorescence; Phosphorescence
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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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    • 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
    • G01N2021/6417—Spectrofluorimetric devices

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Abstract

The present invention relates to one kind enhancing fluorescence probe and preparation method thereof, its chemical structure of general formula is as follows：In formula, R1And R2The alkyl that carbon number is 1~6 is independently selected from, Z is PEG the or PEG derivatives groups that molecular weight is 500~10000.Fluorescence probe intermediate is caused to connect upper two fluorophors by using special MOLECULE DESIGN, and PEG or PEG derivatives are used on the fluorescence probe intermediate, the water solubility of fluorescence probe can be so greatly enhanced, fluorescence intensity is strengthened at double, so as to improve its Detection results to specific molecular (such as singlet oxygen).

Description

One kind enhancing fluorescence probe and preparation method thereof
Technical field
The invention belongs to fluorescence probe field, is related to a kind of enhancing fluorescence probe and preparation method thereof, single available for detection Line state oxygen.
Background technology
Singlet oxygen, the oxygen of the stable ground state oxygen molecule from generally breathing is different, is that one kind is in reactive oxygen species Existence form.Compared with ground state, the chemical property of singlet oxygen is more active, more unstable, and oxidisability is very strong, can cause each The oxidation of kind material.Singlet oxygen can participate in a variety of body biochemical reactions and physiology course, for example, signal transduction, enzyme reaction, Cell division, tissue peroxidating, inflammation, aging, Phagocytosis, tumour and chemical poisoning, the double of Various Complex are produced to body Recast is used.On the one hand, singlet oxygen has stronger toxicity, can cause the damage of body, triggers aging and various diseases；It is and another On the one hand, it is the major antibacterial agent of organism immune system again, it may also be used for the photodynamic therapy of cancer.
At present, a small amount of singlet oxygen is quantitatively detected in the aqueous solution in physiological conditions to have difficulties, essentially consist in its longevity Order that short, reactivity is high.The method of existing singlet oxygen detection is broadly divided into (such as the paramagnetic resonance skill of detection method in gas phase Art, emission spectrum, photo-ionisation technology and calorimetry etc.) and liquid phase in detection method (such as phosphorescence detection method, Chemical Trapping inhale Light photometry, chemoluminescence method, fluorescence detection etc.).Above-mentioned detection method or cost are high-leveled and difficult with application, or because singlet Oxyluminescence efficiency is low and causes sensitivity low, and detecting signal is weak.
The Chinese invention patent of Application No. 201610093502.2 discloses a kind of dyestuff for being used to detect singlet oxygen With fluorescence probe and preparation method thereof, it is fluorescence probe corresponding to Material synthesis by using bridged piperazine derivatives, and be fabricated to inspection Test agent box.Obtained fluorescence probe in this application, has high sensitivity and selectivity to singlet oxygen, greatly expands such The application of fluorescence probe, such as available for the singlet oxygen detection in environment, chemical food and biologic medical field；But It is that the fluorescence intensity of the fluorescence probe still has the space of lifting.
The content of the invention
A kind of enhancing fluorescence probe is provided the invention aims to overcome the deficiencies in the prior art.
To reach above-mentioned purpose, the technical solution adopted by the present invention is：One kind enhancing fluorescence probe, its chemical constitution are led to Formula is as follows：
In formula, R1And R2The alkyl that carbon number is 1~6 is independently selected from, Z is that molecular weight is 500~10000 PEG or PEG derivatives groups.
Optimally, R1And R2It is ethyl.
Optimally, Z isR is O, S or NH.
A further object of the present invention is to provide a kind of preparation method of above-mentioned enhancing fluorescence probe, and it includes following step Suddenly：
Added into reaction vessel Substitution reaction is carried out at 40~80 DEG C；Mole The ratio between amount is 1:2~2.2.
Optimally, it is describedPreparation method comprise the following steps：(a1) willCarry out the substitution reaction of Br free radicals and generate the first product(a2) first production is made Thing carries out substitution reaction with chlorosulfonic acid, generates the second product(a3) by second product with PEG or PEG derivatives carry out substitution reaction.
Because above-mentioned technical proposal is used, the present invention has following advantages compared with prior art：Present invention enhancing fluorescence Probe, make it that fluorescence probe intermediate connects upper two fluorophors by using special MOLECULE DESIGN, and the fluorescence probe PEG or PEG derivatives are used on intermediate, can so be greatly enhanced the water solubility of fluorescence probe, fluorescence intensity is able into Strengthen again, so as to improve its Detection results to specific molecular (such as singlet oxygen).
Brief description of the drawings
Accompanying drawing 1 is the synthetic line figure for strengthening fluorescence probe in embodiment 1；
Accompanying drawing 2 is before and after the enhancing fluorescence probe synthesized in the embodiment of the present invention 1 reacts in room temperature DMF with singlet oxygen Fluorescent emission collection of illustrative plates contrast (λ ex=400nm), wherein1O2Produced within 15 minutes by quick dose of phot-luminescence (rose-red)；
Accompanying drawing 3 is before and after the enhancing fluorescence probe synthesized in the embodiment of the present invention 1 reacts in room temperature water with singlet oxygen Fluorescent emission collection of illustrative plates contrast (λ ex=400nm), wherein1O2Produced within 15 minutes by quick dose of phot-luminescence (rose-red).
Embodiment
Present invention enhancing fluorescence probe, its chemical structure of general formula are as follows：
In formula, R1And R2The alkyl that carbon number is 1~6 is independently selected from, Z is that molecular weight is 500~10000 PEG or PEG derivatives groups.Fluorescence probe intermediate is caused to connect upper two fluorescent bases by using special MOLECULE DESIGN Group, and PEG or PEG derivatives are used on the fluorescence probe intermediate, the water solubility of fluorescence probe can be so greatly enhanced, Fluorescence intensity is strengthened at double, so as to improve its Detection results to specific molecular (such as singlet oxygen).
R1And R2Both preferably ethyl.Z be preferably methoxyl group modification PEG or PEG derivatives, R O, S or NH.Above-mentioned increasing The chemical structure of general formula of hyperfluorescence probe is optimal to be
N size is according to specific molecular weight It is determined that.
The preparation method of above-mentioned enhancing fluorescence probe, it comprises the following steps：
Added into reaction vessel Substitution reaction is carried out at 40~80 DEG C；Mole The ratio between amount is 1:2~2.2.
It is and describedPreparation method comprise the following steps：(a1) willEnter The substitution reaction of row Br free radicals generates the first product(a2) first product is made to be taken with chlorosulfonic acid Generation reaction, generates the second product(a3) second product is entered with PEG or PEG derivatives Row substitution reaction.AndThen byIt is anti-with piperazine It should be made.
The present invention is further described below in conjunction with accompanying drawing embodiment.
Embodiment 1
The present embodiment provides a kind of enhancing fluorescence probe and preparation method thereof, and the chemical structural formula of the enhancing fluorescence probe is such as Under：Its preparation method is as follows, comprises the following steps (as shown in Figure 1)：
(a1) in 50mL there-necked flasks, and addition HOCD (1g, 2.43mmol, 1eq, i.e.,), carbon tetrachloride (10mL), NBS (0.95g, 5.36mol, 2.2eq, i.e. N-bromosuccinimide), benzoyl peroxide (5.88mg, 0.0243mmol, 0.01eq), it is heated to reflux 19 hours under nitrogen protection, is cooled to 0 DEG C, filtering, filter cake is washed with carbon tetrachloride Wash, concentrate, then by column chromatography, obtain compound 1.24g (90%) blue solid (first product).Survey Hydrogen modal data be：1H NMR(300MHz,CDCl3)δ(ppm):8.81 (s, 2H), 8.75 (d, J=6.0Hz, 2H), 8.28 (s, 2H), 8.25 (d, J=6.0Hz, 2H), 7.59-7.56 (m, 4H), the carbon modal data that 2.57 (s, 4H) are measured are：13C NMR (75MHz,CDCl3)d(ppm):1884.73,141.09,136.67,134.96,134.06,132.62,131.58,130.21, 129.10,128.66,128.71,126.38,124.29,26.45.HREI-MS m/z calcd:C30H18Br2O2([M]+)； 567.9674,found:567.9665；
(a2) in 50mL single port bottles, the first product (800mg, 1.38mmol, 1eq) is added, adds chlorosulfonic acid (16mL), It is heated to reflux 24 hours, reaction solution is added in 20mL frozen water, extracted with dichloromethane, concentrated post purifies to obtain compound 2 652mg (71%) blue solid (second product)。1H NMR(300MHz,CDCl3)δ(ppm): 9.25 (d, J=3.0Hz, 1H), 8.75 (d, J=9.0Hz, 1H), 8.58-6.53 (m, 2H) 8.15 (s, 2H), 7.98-7.89 (m,3H),7.59-7.52(m,2H),2.53(s,2H),2.51(s,2H).13C NMR(75MHz,CDCl3)δ(ppm): 182.94,182.91,142.05,140.67,140.15,134.57,134.14,132.93,132.58,131.40,131.34, 130.80,130.70,130.63,130.00,129.78,129.64,129.54,129.39,129.26,129.17,128.88, 128.39,128.09,126.22,125.36,121.68,21.45ppm.HRESI-MS:m/z cacld.C30H17Br2ClO4S: 665.8903(M+),found:665.8895(weak peak).Cacld:C30H18Br2O5S[M-H]-646.9242 (sulfonate),found:647.9235(strong peak)；
(a3) in 50mL single port bottles, the second product (200mg, 0.3mmol, 1eq) is added, adds dichloromethane (5mL), Et3N (triethylamine, 37mg, 0.36mmol, 1.2eq), methoxy poly (ethylene glycol) (i.e. mPEG-OH, MW=1000) (23mg, 0.36mmol, 1.2eq), react 5 hours at 50 DEG C, be cooled to room temperature, water 1mL on the rocks, concentration, cross post and purify to obtain tertiary industry Thing 144mg is (i.e.68%) blue solid1H NMR(300MHz,CDCl3)δ (ppm):9.27(m,1H),8.79(m,1H),8.68-6.57(m,2H)8.25(m,2H),7.98-7.89(m,3H),7.59- 7.52(m,2H),4.25-4.20(m,2H),3.63-3.60(m,3H),3.45-3.42(m,2H),2.53(m,2H),2.51(m, 2H)；
(b1) take piperazine (5.31mg, 0.062mmol) to be dissolved in dry methylene chloride (DCM) (6mL), then add benzo Triazole-N, N, N', N'-15 tetramethylurea hexafluorophosphate (HBTU) (34.3mg, 0.091mmol), N, N- diisopropyl second After base amine (DIPEA) (31 μ L, 0.184mmol), withIn room It is stirred overnight, produces under temperatureCrude product.Product is purified：Respectively with HCl (1M, 10mL) and NaHCO3The aqueous solution (2 times, each 10mL) washing reaction mixture；Collect organic phase and rotary evaporated to dryness is dry.It is logical Cross silica gel column chromatography (eluent：CH2Cl2/ MeOH, 20v/v=97：3) purification of crude product, pure violet compound is obtained (27.4mg, 89%).1H NMR (300MHz, CDCl3) δ=8.76 (d, J=9Hz, 1H), 8.68 (d, J=9Hz, 1H), 8.31 (d, J=6Hz, 2H), 7.57-7.49 (m, 5H), 7.40-7.35 (m, 3H), 7.11 (d, J=6Hz, 1H), 3.94 (d, J= 12H, 1H), 3.26 (d, J=12H, 1H), 2.98-2.67 (m, 5H), 2.56 (s, 3H), 2.50 (s, 3H), 2.32 (t, J= 12H, 1H)；13C NMR (126MHz, CDCl3) δ=184.72,168.67,139.35,138.39,138.26,135.00, 134.34,133.66,133.62,133.56,132.15,130.75,129.65,129.21,128.82,128.23,128.14, 127.59,127.14,126.66,126.14,126.06,125.79,5 125.64,47.96,45.39,41.28,21.55, 21.37.C34H29N2O2[M]+HRESI-MS Cacld:497.2224；found:497.2225.
(c) in 50mL single port bottles, third product (100mg, 0.141mmol, 1eq), CH are added3CN(5mL),K2CO3 (98mg, 0.705mmol, 5.0eq) and70℃ Lower reaction 8 hours, is cooled to room temperature, concentrates, and fluorescence probe 150mg (68%) light red solid must be strengthened by crossing post and purifying.1H NMR (300MHz, CDCl3) δ=9.08 (s, 1H), 8.79-8.73 (m, 6H), 8.23 (s, 4H), 8.17 (m, 3H), 8.04 (m, 6H), 7.78 (d, 3H), 7.62 (s, 4H), 7.45 (m, 3H), 6.92 (m, 3H), 4.25-4.20 (m, 2H), 3.63-3.60 (m, 3H), 3.45-3.42 (m, 28H), 3.26-3.14 (m, 10H), 2.54m, 6H), 2.53 (m, 6H), 1.25 (m, 12H).
Embodiment 2
The present embodiment provides a kind of enhancing fluorescence probe and preparation method thereof, the chemical structural formula of the enhancing fluorescence probe and Reactions steps with basically identical in embodiment 1, unlike：(a3) the mPEG-OH molecular weight used in is 10000, step (b1) raw material used in is
Embodiment 3
The present embodiment provides a kind of enhancing fluorescence probe and preparation method thereof, the chemical structural formula of the enhancing fluorescence probe and Reactions steps with basically identical in embodiment 1, unlike：(a3) the mPEG-OH molecular weight used in is 500.
3 parts of photosensitizer rose bengals (2 μ L, 0.5mg/mL, be dissolved in 10mM PBSs, pH=7.4) stock solution is taken, respectively The probe mixing added in embodiment 1 to embodiment 3；By solution several minutes under the light of fiber luminaire, and with glimmering Photometry records fluorescence intensity change.Wherein, shown in experimental result Fig. 2 in embodiment 1, enhancing fluorescence probe DMF (1 μM) with Fluorescence excitation spectral intensity enhances 148 times respectively after singlet oxygen reaction；And obtained enhancing is glimmering in embodiment 2 and embodiment 3 Fluorescence excitation spectral intensity enhances 146 times to light probe respectively, 145 times (with application number after DMF (1 μM) and singlet oxygen reaction For the IIIa probes in 201610093502.2 Chinese invention patents as a comparison case, measure and add 60 times), it is clear that they are big It is higher than comparative example greatly.In the PBS of simulation biological physiology environment, concentration is 0.1 μM of probe and single line in comparative example 1 Fluorescence excitation spectrum distinguishes intensity 120 times (as shown in Figure 3) after the reaction of state oxygen；And obtained enhancing in embodiment 2 and embodiment 3 Fluorescence excitation spectral intensity enhances 116 times, 115 times respectively after fluorescence probe reacts in PBS with singlet oxygen, about 80% measured in organic solvent DMF, this illustrate the probe it is water-soluble not than oil-soluble reduce how much, have good It is water-soluble.
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 can understand present disclosure and implement according to this, and it is not intended to limit the scope of the present invention, all according to the present invention The equivalent change or modification that Spirit Essence is made, it should all be included within the scope of the present invention.

Claims (5)

1. one kind enhancing fluorescence probe, it is characterised in that its chemical structure of general formula is as follows：
In formula, R1And R2Be independently selected from carbon number be 1~6 alkyl, Z be the PEG that molecular weight is 500~10000 or PEG derivatives groups.
2. enhancing fluorescence probe according to claim 1, it is characterised in that：R1And R2It is ethyl.
3. enhancing fluorescence probe according to claim 1, it is characterised in that：Z isR is O, S Or NH.
4. the preparation method of any enhancing fluorescence probe in claims 1 to 3, it is characterised in that it comprises the following steps：
Added into reaction vesselCH3CN、K2CO3With 40~80 DEG C of progress substitution reactions；Mole The ratio between be 1:2~2.2.
5. strengthen the preparation method of fluorescence probe according to claim 4, it is characterised in that：It is described Preparation method comprise the following steps：
(a1) willCarry out the substitution reaction of Br free radicals and generate the first product
(a2) first product is carried out substitution reaction with chlorosulfonic acid, generate the second product
(a3) second product and PEG or PEG derivatives are subjected to substitution reaction.
CN201711210236.8A 2017-11-28 2017-11-28 One kind enhancing fluorescence probe and preparation method thereof Pending CN107857876A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110256644A (en) * 2019-05-20 2019-09-20 徐从燕 It is a kind of for detecting the fluorescence probe and preparation method thereof of heavy metals in industrial wastewater ion

Citations (4)

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Publication number Priority date Publication date Assignee Title
CN1953960A (en) * 2004-05-12 2007-04-25 出光兴产株式会社 Aromatic amine derivative, organic electroluminescent device using the same, and method for preparing aromatic amine derivative
CN102300861A (en) * 2009-02-03 2011-12-28 百奥提姆股份有限公司 Xanthene dyes comprising a sulfonamide group
WO2012039685A1 (en) * 2010-09-24 2012-03-29 Agency For Science, Technology And Research A nanoprobe comprising gold colloid nanoparticles for multimodality optical imaging of cancer and targeted drug delivery for cancer
CN107099165A (en) * 2016-02-19 2017-08-29 苏州工业园区新国大研究院 Dyestuff and fluorescence probe for detecting singlet oxygen and preparation method thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1953960A (en) * 2004-05-12 2007-04-25 出光兴产株式会社 Aromatic amine derivative, organic electroluminescent device using the same, and method for preparing aromatic amine derivative
CN102300861A (en) * 2009-02-03 2011-12-28 百奥提姆股份有限公司 Xanthene dyes comprising a sulfonamide group
WO2012039685A1 (en) * 2010-09-24 2012-03-29 Agency For Science, Technology And Research A nanoprobe comprising gold colloid nanoparticles for multimodality optical imaging of cancer and targeted drug delivery for cancer
CN107099165A (en) * 2016-02-19 2017-08-29 苏州工业园区新国大研究院 Dyestuff and fluorescence probe for detecting singlet oxygen and preparation method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110256644A (en) * 2019-05-20 2019-09-20 徐从燕 It is a kind of for detecting the fluorescence probe and preparation method thereof of heavy metals in industrial wastewater ion
CN110256644B (en) * 2019-05-20 2021-12-14 徐从燕 Fluorescent probe for detecting heavy metal ions in industrial wastewater and preparation method thereof

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