CN107235984A - 含氨基吡啶环的罗丹明B的Fe3+传感器、制备方法及应用 - Google Patents
含氨基吡啶环的罗丹明B的Fe3+传感器、制备方法及应用 Download PDFInfo
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 229940043267 rhodamine b Drugs 0.000 title claims abstract description 11
- MUKAGFLFIMVSQN-UHFFFAOYSA-N 3-n-benzylpyridine-2,3-diamine Chemical compound NC1=NC=CC=C1NCC1=CC=CC=C1 MUKAGFLFIMVSQN-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000001514 detection method Methods 0.000 claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 229940125904 compound 1 Drugs 0.000 claims description 7
- 229940125782 compound 2 Drugs 0.000 claims description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
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- 229940054066 benzamide antipsychotics Drugs 0.000 abstract 1
- 150000003936 benzamides Chemical class 0.000 abstract 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000011835 investigation Methods 0.000 abstract 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 abstract 1
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- 230000003287 optical effect Effects 0.000 description 8
- 229910021645 metal ion Inorganic materials 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- 239000000523 sample Substances 0.000 description 5
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
- 239000007995 HEPES buffer Substances 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- RLJMLMKIBZAXJO-UHFFFAOYSA-N lead nitrate Chemical compound [O-][N+](=O)O[Pb]O[N+]([O-])=O RLJMLMKIBZAXJO-UHFFFAOYSA-N 0.000 description 4
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- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IWOUKMZUPDVPGQ-UHFFFAOYSA-N barium nitrate Inorganic materials [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- DZVRGWYMCGLNKJ-UHFFFAOYSA-J cadmium dichloride hemipentahydrate Chemical compound O.O.O.O.O.Cl[Cd]Cl.Cl[Cd]Cl DZVRGWYMCGLNKJ-UHFFFAOYSA-J 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WSSMOXHYUFMBLS-UHFFFAOYSA-L iron dichloride tetrahydrate Chemical compound O.O.O.O.[Cl-].[Cl-].[Fe+2] WSSMOXHYUFMBLS-UHFFFAOYSA-L 0.000 description 2
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 0 *CC(NCc1ncccc1)=O Chemical compound *CC(NCc1ncccc1)=O 0.000 description 1
- SLBPIHCMXPQAIQ-UHFFFAOYSA-N 8-hydroxyquinoline-2-carbaldehyde Chemical compound C1=C(C=O)N=C2C(O)=CC=CC2=C1 SLBPIHCMXPQAIQ-UHFFFAOYSA-N 0.000 description 1
- HSABBFJVLMEXKT-UHFFFAOYSA-N CCN(CC)c1ccc(C(c2ccccc22)(c(c(O3)c4)ccc4N(CC)CC)N(CCN)C2=O)c3c1 Chemical compound CCN(CC)c1ccc(C(c2ccccc22)(c(c(O3)c4)ccc4N(CC)CC)N(CCN)C2=O)c3c1 HSABBFJVLMEXKT-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
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- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 238000010859 live-cell imaging Methods 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- 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
- 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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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- 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
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
本发明公开了一种含氨基吡啶环的罗丹明B的Fe3+传感器、制备方法及应用。本发明以罗丹明B（Rhodanmine B)为前体合成目标产物N‑(2‑(3',6'–二(二乙基氨基)‑3‑氧代螺‑[异二氢吲哚‑1,9'‑咕吨]‑2‑基)乙基)‑4‑苯甲酰胺‑(2,5‑二氧‑2,5‑二氢‑1H‑吡咯‑1‑基)。本发明提供了目标产物在Fe3+检测中的应用，通过紫外可见光和荧光测试后，发现加入Fe3+后，紫外吸收值和荧光强度均有显著的变化，与现有技术相比，本发明采用的原料易得，合成步骤简单，后处理易很方便，较易实现大规模生产，该种传感器在检测生物活体以及环境中的Fe3+方面有很大的应用前景。
Description
技术领域
本发明属于生物化学领域，具体涉及一种含氨基吡啶环的罗丹明B的Fe3+传感器、制备方法及应用。
背景技术
目前，常用检测Fe3+的方法为原子吸收法(AAS)、分光光度法、电感耦合等离子体发射光谱法(ICP-AES)、电感耦合等离子体质谱法(ICP-AES)、电化学法等，通常需要复杂的仪器和复杂的样品预处理过程。由于该技术不仅操作简单、成本低、灵敏度高、选择性好、响应时间短，近来荧光探针法受到了极大的关注。
由于Fe3+是3d5结构的顺磁性离子,对荧光具有极强的猝灭性,因此大多数报道的Fe3+荧光探针都是荧光猝灭型的，在探针识别客体时荧光猝灭不利于高通量信号输出。因此，利用罗丹明分子的“OFF-ON”环转换机理设计的荧光增强型Fe3+荧光探针受到极大重视。
文献1(Narendra Reddy Chereddy,Peethani Nagaraju,M.V.Niladri Raju,etal.A novel FRET‘off–on’fluorescent probe for the selective detection of Fe3+,Al3+,and Cr3+, ions:Its ultrafast energy transfer kinetics and application inlive cell imaging[J]. Biosensors&Bioelectronics,2015,68,749-756)报道了一种利用罗丹明酰肼与8-羟基喹啉-2-醛合成的席夫碱和萘二甲酰亚胺—哌嗪衍生物进行缩合，合成出一种新型的Fe3+传感器的方法，产率65％。
文献2(Ali Molla H,Rahul B,Atul K,Keya C,Sumana G and Mahammad A,Anovel rhodamine-3,4-dihydro-2H-1,3-benzoxazine conjugate as a highlysensitive and selective chemosensor for Fe3+ions with cytoplasmic cell imagingpossibilities[J].Anal. Methods,2015,7,5149-5156.)报道了一种利用罗丹明类衍生物和2,4-二叔丁基苯酚、甲醛缩合，合成出一种新型的Fe3+传感器的方法，产率68％。
上述文献所报道的合成方法存在以下缺陷
(1)如文献1中，选择性不是很好，Cr3+和Al3+荧光响应显著,对Fe3+检测干扰较大。
(2)如文献2中，体外检测是在乙腈/水混合溶剂体系中进行，且乙腈在混合溶剂体系中的体积比例达到了70％。
上述缺陷造成至今为止，应用现有工艺方法难以得到合成简单，产率高而且选择性较好的Fe3+传感器制备方法。
发明内容
本发明目的是提供一种含氨基吡啶环的罗丹明B的Fe3+传感器、制备方法及应用。
实现本发明目的的技术解决方案是：
一种含氨基吡啶环的罗丹明B的Fe3+传感器，该荧光传感器的结构如下：
本发明中含氨基吡啶环的罗丹明B的Fe3+传感器的制备方法，包括以下步骤：
将化合物1置于乙腈中重悬，然后加入化合物2、K2CO3、KI，回流反应，反应完成之后，减压除去溶剂，萃取，硅胶柱分离，得到所述Fe3+荧光传感器，其中，化合物1和化合物2的结构如下：
进一步的，反应物摩尔比计为，化合物1：化合物2：K2CO3：KI＝1eq：1.2eq： 1eq：1eq。
进一步的，回流反应时间为20-24h。
进一步的，硅胶柱分离采用的洗脱液为MeOH：CH2Cl2＝3：100(v/v)。
本发明中所述的基于罗丹明B的Fe3+荧光传感器用于检测Fe3+。
本发明与现有技术相比，其显著优点是：(1)本发明以罗丹明为主体合成了一种新型Fe3+荧光传感器，具有良好的光稳定性，长波长发射以及量子产率高等优点。(2 )本发明所涉及传感器对Fe3+检测具有优良的专一性。(3)本发明所采用原材料成本低，合成步骤简单，后处理亦很方便，交易实现大规模生产。(4)本发明所涉及传感器能选择性检测Fe3+，且敏感度较好，在检测生物样品和细胞中的Fe3+方面具有很大的应用前景。
附图说明
图1为本发明的化合物L3 1H NMR。
图2为本发明的化合物L3 13C NMR。
图3为本发明的化合物L3的紫外选择性(其中横坐标为波长，单位：nm；纵坐标为吸收值)。
图4为本发明的化合物L3的荧光选择性(其中横坐标为波长，单位：nm；纵坐标为荧光强度)。
具体实施方式
(一)传感器化合物的合成
本发明提供了目标产物在Fe3+检测中的应用，发现其对Fe3+有很好的检测效果。本发明合成路线如下：
(二)紫外选择性能测试
将FeCl3.6H2O,CrCl3.6H2O,AlCl3,CuCl2.2H2O,MgCl2·6H2O,CdCl2.2.5H2O,FeCl2.4H2O,NiCl2.6H2O,MnCl2.4H2O,CoCl2.6H2O,Pb(NO3)2,AgNO3,Ba(NO3)2,CaCl2, ZnCl2,HgCl2,CuCl,KCl,NaCl等不同金属离子氯化物或硝化物加入化合物L3的溶液中，进行紫外吸收测试。下面结合附图和具体实施例对本发明作进一步详细说明。
(三)荧光性能测试
将FeCl3.6H2O,CrCl3.6H2O,AlCl3,CuCl2.2H2O,MgCl2·6H2O,CdCl2.2.5H2O,FeCl2.4H2O,NiCl2.6H2O,MnCl2.4H2O,CoCl2.6H2O,Pb(NO3)2,AgNO3,Ba(NO3)2,CaCl2, ZnCl2,HgCl2,CuCl,KCl,NaCl等不同金属离子氯化物或硝化物加入化合物L3的溶液中，进行荧光响应测试。下面结合附图和具体实施例对本发明作进一步详细说明。
实施例1
荧光化学传感器的合成
化合物L3的合成
将化合物1((200mg,1.083mmol)溶解于乙腈(25mL)中，加入化合物2(630 mg,1.30mmol)、K2CO3(149mg，1.083mmol)，KI(179mg，1.083mmol)待回流反应20-24h之后，冷却至室温，减压除去溶剂，萃取，经柱分离之后最终得到红棕色固体(342mg，50.04％)。化合物L3 1H NMR，13C NMR分别如图1，图2所示。
实施例2
紫外选择性能测试
Fe3+荧光传感器L3在甲醇中具有很好的溶解性，经验证，化合物L3可以溶解在MeOH：HEPES(0.6mM，1/1，V/V)混合液中，配制500mL该溶液作为储备液 (pH＝7.23)。
精确配置Fe3+荧光传感器L3为1×10-3mol/L MeOH-H2O混合液(1/1，V/V)，金属离子Fe3+,Cr3+,Al3+,Cu2+,Mg2+,Cd2+,Fe2+,Ni2+,Mn2+,Co2+,Pb2+,Hg2+,Ag+,Ba2+, Ca2+,Zn2+,K+,Na+,Cu+等浓度为5×10-3mol/L水溶液，以及用MeOH：HEPES(0.6mM, pH＝7.23，1/1,V/V)溶液。
紫外选择性实验如图3所示，取3mL储备液置于液体池中，加入60μL Fe3+荧光传感器L3溶液，测其初始紫外吸收值，然后分别加入配置好的各种金属离子溶液60 μL，测量其稳定的时的紫外吸收强度。观察图3可知，化合物L3对Fe3+有明显的响应效果，并且在558nm处的紫外吸收强度达到最大值，也即化合物L3对Fe3+有很好的选择性。
实施例3
荧光性能测试
Fe3+荧光传感器L3在甲醇中具有很好的溶解性，经验证，化合物L3可以溶解在MeOH：HEPES(0.6mM，1/1，V/V)混合液中，配制500mL该溶液作为储备液 (pH＝7.23)。
精确配置Fe3+荧光传感器L3为1×10-3mol/L MeOH-H2O混合液(1/1，V/V)，金属离子Fe3+,Cr3+,Al3+,Cu2+,Mg2+,Cd2+,Fe2+,Ni2+,Mn2+,Co2+,Pb2+,Hg2+,Ag+,Ba2+, Ca2+,Zn2+,K+,Na+,Cu+等浓度为5×10-3mol/L水溶液，以及用MeOH：HEPES(0.6mM, pH＝7.23，1/1,V/V)溶液。
荧光选择性实验如图4所示，取3mL储备液置于液体池中，加入60μL Fe3+荧光传感器L3溶液，测其初始荧光强度值，然后分别加入配置好的各种金属离子溶液和氨基酸溶液60μL，测量其稳定时的荧光强度。观察图4可知，化合物L3对Fe3+有明显的响应效果，并且在582nm处荧光强度达到最大值，也即化合物L3对Fe3+有很好的选择性。
Claims (6)
1.含氨基吡啶环的罗丹明B的Fe3+传感器，其特征在于，该Fe3+传感器的结构如下：
2.含氨基吡啶环的罗丹明B的Fe3+传感器的制备方法，其特征在于，包括以下步骤：
将化合物1置于乙腈中重悬，然后加入化合物2、K2CO3、KI，回流反应，反应完成之后，减压除去溶剂，萃取，硅胶柱分离，得到所述Fe3+传感器，其中，化合物1和化合物2的结构如下：
3.如权利要求2所述的方法，其特征在于，反应物摩尔比计为，化合物1：化合物2：K2CO3：KI＝1eq：1.2eq：1eq：1eq。
4.如权利要求2所述的方法，其特征在于，回流反应时间为20-24h。
5.如权利要求2所述的方法，其特征在于，硅胶柱分离采用的洗脱液是体积比为MeOH：CH2Cl2＝3：100的混合液。
6.如权利要求1所述的含氨基吡啶环的罗丹明B的Fe3+传感器在检测Fe3+上的应用。
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