CN108285454A - A kind of Fe containing amino acid3+Fluorescence probe and its synthetic method - Google Patents
A kind of Fe containing amino acid3+Fluorescence probe and its synthetic method Download PDFInfo
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- CN108285454A CN108285454A CN201810387045.7A CN201810387045A CN108285454A CN 108285454 A CN108285454 A CN 108285454A CN 201810387045 A CN201810387045 A CN 201810387045A CN 108285454 A CN108285454 A CN 108285454A
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Abstract
The invention belongs to fluorescence probe material and its preparation fields, and in particular to a kind of Fe containing amino acid3+Fluorescence probe and its synthetic method, its structural formula is as shown in the figure, including high sensitivity, good light stability, fluorescence quantum yield is high, the rhodamine fluorogen of wavelength length, the serine of good water solubility, a certain amount of rhodamine lactams occur condensation reaction with serine and obtain the Fe containing amino acid of special construction under certain condition3+Fluorescence probe, building-up process raw material is simple and easy to get, reaction condition is mild, easy to operate, while gained Rhodamine fluorescent probe can quickly detect Fe in biological cell under water environment3+, to Fe3+Combination belong to corrdination type identification, have invertibity.
Description
Technical field
The invention belongs to fluorescence probe material and its preparation fields, and in particular to a kind of Fe containing amino acid3+Fluorescence probe
And its synthetic method.
Background technology
Contain abundant ferro element in human body, average each adult about contains 3-5g, and the concentration in entire cell is about
For 50-100 μ Μ (Epsztejn, S., Glickstein, H., Picard, V., Slotki, I.N., Breuer, W.,
Beaumont,C.,Cabantchik,Z.I.H-ferritin subunit overexpression in erythroid
cells reduces the oxidative stress response and induces multidrug resistance
propertie[J].Blood 1999,94(10),3593-3603).It is directed to ferro element in most cellular processes in human body,
Such as metabolism, the synthesis of electronics transfer and DNA.It is Fe that usual ferro element, which exists in human body with two kinds of ionic species,2+And Fe3+,
Two kinds of ions can be in certain equilibrium state in cellular physiological processes.Therefore the content of iron in cell must be controlled, point
Cloth and iron ion form will cause the unbalance of body, such as anaemia, blood if normal ferro element operation is destroyed in human body
Color thesaurismosis and senile dementia, therefore be of great significance to the detection of iron ion.
The main method of detection ferro element has at present：Atomic absorption spectrography (AAS), plasma incude spectroscopic methodology, inductive coupling
Plasma emission spectrometry, Inductively coupled plasma-mass spectrometry, electrochemical sensing etc., but these methods are there are expensive equipment,
It is strongly professional, it takes, there is the destructive loss that will also result in detectable substance simultaneously to sample.
It can be seen that the method for early detection iron ion lacks and influences its biological function, and fluorescence probe is very attractive
Tool, can distribution and species of the direct visual perception to unstable iron ion formed.However since iron has paramagnetism, meeting
Cause Quenching of fluorescence, therefore the fluorescence probe of early stage is mostly quenching type, and at the same time two kinds of ionic conditions of detection ferro element,
Gu the selectivity and sensitivity to detection have a great impact.Therefore the synthesis of rhodamine off-on mechanismic designs is utilized in recent years
Rhodamine fluorescence probe being capable of selective enumeration method Fe well2+Or Fe3+。
Hirayama et al. (Hirayama, T., Okuda, K., Nagasawa, H.A highly selective turn-
on fluorescent probe for iron(II)to visualize labile iron in living cells[J]
.Chem.Sci.2013,4 (3), 1250-1256.) synthesize a kind of and Fe2+The rhodamine base fluorescent probe reacted, it is former
Reason is Fe2+By N-O- radical decompositions on probe, it is reduced to tertiary amino group.When there are Fe in cell3+When, this reaction will not carry out,
Therefore cell need to be handled with chelating agent.Although probe can selectively identify Fe as the fluorescence imaging of active somatic cell2+, still
Its detection mechanism can't show invertibity, to limit ability Fe unstable under probe in detecting flowing2+。
Yang et al. (Han OuYang, Yong Gao, Yaofeng Yuan.A highly selective
rhodamine-based optical-electrochemical multichannel chemosensor for Fe3+[J]
.Tetrahedron Letters, 2013,54,2964-2966.) using rhodamine lactams conjunction is reacted with ferrocene formyl chloride
At fluorescence probe, this probe is in CH3CN-H2O(1:1, v/v) to Fe in solution3+With good selectivity, in addition to Cr3+,Fe2+,
Hg2+And Cu2+Have outside interference, solution occurs significantly becoming red from colourless, the UV absorption enhancing at 560nm, at 583nm
Fluorescence intensity enhancing, can obviously see solution after addition EDTA into solution and become colorless by red, this illustrates that probe has
Invertibity.But this probe need to 50% CH3It could be dissolved in CN aqueous solutions, there is certain toxicity to cell.
Patent No. CN201310409868.2 discloses a kind of Novel rhodamine fluorescence probe, belongs to functional material neck
Domain.For raw material, rhodamine lactams is prepared with diamine modification RhB with rhodamine B (RhB) for the fluorescence probe of the present invention,
And then reacted with maleic anhydride (MAH) and amantadine, rhodamine fluorescence probe is prepared, containing in structure can be with gold
Belong to multiple amido functional groups for having an effect of ion and can be with Hg2+The carbon-carbon double bond of effect.Helical form rhodamine lactams chemical combination
Object with heavy metal particles after being combined, and the protonation of lactams nitrogen-atoms will cause nitrogen-atoms charge density to reduce, to cause
The cracking of spiral center C-N keys generates change in fluorescence and color change.The Rhodamine Derivatives of gained of the invention are in aqueous solution
Mercury ion and iron ion all have preferable recognition capability, reach 8.3ppm to iron ion detectable limit, to mercury ion detecting pole
Limit for height reaches 4.7ppm, therefore the probe does not have specificity, is easily influenced or detected mercury by mercury ion when detecting iron ion
It is easily influenced by iron ion when ion.
Therefore in order to overcome analytical instrument it is expensive, it is strongly professional, time-consuming, there is the problems such as destructive and current glimmering to sample
The problems such as light probe has irreversibility, and specificity is poor, poorly water-soluble, design synthesis is a kind of, and there is invertibity, good water solubility to resist
The strong novel fluorescence probe of interference performance has great importance.
Invention content
In order to solve above-mentioned expensive equipment, it is strongly professional, time-consuming, there is the problems such as destructive and current fluorescence to visit to sample
The problems such as irreversibility, specificity existing for needle be poor, poorly water-soluble, the present invention provides a kind of Fe containing amino acid3+Fluorescence probe
And its synthetic method.
A kind of Fe containing amino acid3+Fluorescence probe, structural formula are as shown in Figure 1.
Further, the Fe containing amino acid3+Group R1, R2, R3, R4 H or group R1 and R2 in fluorescence probe structural formula
For CH3, group R3 and R4 are H or group R1 and R2 are C2H5, group R3 and R4 are H or group R1 is C2H5, group R2 and R3
It is CH for H, group R43。
Further, the Fe containing amino acid3+N is 0,2,3 in fluorescence probe structural formula ... n.
A kind of Fe containing amino acid3+The synthetic method of fluorescence probe prepares the above-mentioned Fe containing amino acid3+Fluorescence probe,
Its synthetic method is as follows：
Step 1：The bright lactam intermediate of synthesizing rhodamine, weighs 2-3g rhodamines, is dissolved in organic solvent, connect
It and aminated compounds solution is added dropwise in rhodamine solution, be heated to 50-60 DEG C, obtained after back flow reaction 2-7h
Rhodamine lactam intermediate；
Step 2：Synthesize the Fe containing amino acid3+Fluorescence probe weighs 1-2mmol rhodamine lactams, is dissolved in organic
Serine solution is then added dropwise in rhodamine lactams solution by solvent, is heated to 60-85 DEG C, is flowed back, thin-layer chromatography
It tracks to reaction to terminate, target compound is obtained by column chromatographic isolation and purification after reaction.
Further, organic solvent is methanol, ethyl alcohol, acetonitrile.
Further, the molar ratio of rhodamine lactams and serine is 1:1.0-1.5.
Further, the reaction temperature of synthesising target compound is 80 DEG C.
Further, column chromatographic isolation and purification solvent is dichloromethane and ethyl alcohol.
Further, column chromatographic isolation and purification methylene chloride and the volume ratio of ethyl alcohol are 160-220:1.
Have preferable water-soluble the present invention is based on rhodamine and serine, designs a kind of the water-soluble of special construction
Fe of the property containing amino acid3+Fluorescence probe.With serine condensation reaction occurs under certain condition for a certain amount of rhodamine lactams
Obtain the Fe containing amino acid3+Fluorescence probe, building-up process raw material is simple and easy to get, reaction condition is mild, easy to operate, while gained
Rhodamine fluorescent probe can quickly detect Fe in biological cell under water environment3+, and do not interfered by other metal ions, have
There is specificity, to Fe3+Combination belong to corrdination type identification, have invertibity.
Description of the drawings
Fig. 1 is the Fe containing amino acid3+The structural formula of fluorescence probe；
Fig. 2 is the Fe containing amino acid3+Fluorescence emission spectrogram of compound of the fluorescence probe to metalloform-selective；
Fig. 3 is the Fe containing amino acid3+Fe of the fluorescence probe to 3eq3+With the fluorescence emission spectrum of the other interfering ions of 5eq
Figure；
Fig. 4 is the Fe containing amino acid3+Fluorescence probe is to different Fe3+The fluorescence emission spectrogram of compound of concentration；
Fig. 5 is the Fe containing amino acid3+The fluorescence emission spectrogram of compound of fluorescence probe reversibility test.
Specific implementation mode
As shown in Figure 1, a kind of Fe containing amino acid3+Fluorescence probe, specific embodiment are as follows：
Embodiment one
A kind of Fe containing amino acid3+Fluorescence probe, synthesis group R1, R2, R3, R4 H, the rhodamine 110Fe that n is 23+
Fluorescence probe.
A kind of Fe containing amino acid3+The synthetic method of fluorescence probe prepares above-mentioned rhodamine 110Fe3+Fluorescence probe,
Its synthetic method is as follows：
Step 1：Among bright 110 lactams of synthesizing rhodamine, 110 dyestuff of 2g rhodamines is weighed, alcohol solvent is dissolved in,
Then ethylenediamine solution is added dropwise in 110 solution of rhodamine, is heated to 50 DEG C, back flow reaction 6h, it is molten in reaction process
Liquid becomes orange-yellow by purplish red, obtains 110 lactam intermediate of rhodamine；
Step 2：The bright 110Fe of synthesizing rhodamine3+Fluorescence probe weighs 110 lactams of 1mmol rhodamines, is dissolved in ethyl alcohol
1.2mmol serine solution is then added dropwise in 110 lactams solution of rhodamine by solvent, is heated to 80 DEG C, is flowed back,
Thin-layer chromatography, which tracks to reaction, to be terminated, and obtains target compound, column chromatography for separation by column chromatographic isolation and purification after reaction
Purification solvent ethyl alcohol is 1 with methylene chloride volume ratio:200.
Embodiment two
A kind of Fe containing amino acid3+Fluorescence probe, synthesis group R1 and R2 are CH3, group R3 and R4 be H, n be 2 four
Rhodamine Fe3+Fluorescence probe.
A kind of Fe containing amino acid3+The synthetic method of fluorescence probe prepares above-mentioned tetramethylrhodamine Fe3+Fluorescence is visited
Needle, synthetic method are as follows：
Step 1：It synthesizes among tetramethylrhodamine lactams, weighs 2g tetramethylrhodaminedye dyes, be dissolved in ethyl alcohol
Ethylenediamine solution is then added dropwise in tetramethylrhodamine solution by solvent, is heated to 50 DEG C, back flow reaction 6h, reaction
Solution becomes orange-yellow by purplish red in the process, obtains tetramethylrhodamine lactam intermediate；
Step 2：Synthesize the Fe containing amino acid3+Fluorescence probe weighs 1mmol tetramethylrhodamine lactams, is dissolved in
1.2mmol serine solution is then added dropwise in tetramethylrhodamine lactams solution, is heated to 80 by alcohol solvent
DEG C, reflux, thin-layer chromatography, which tracks to reaction, to be terminated, and obtains target compound, column by column chromatographic isolation and purification after reaction
Chromatography purification solvent ethyl alcohol is 1 with methylene chloride volume ratio:200.
Embodiment three
A kind of Fe containing amino acid3+Fluorescence probe, synthesis group R1 and R2 are C2H5, group R3 and R4 be H, n is 2 to contain
The Fe of amino acid3+Fluorescence probe.
A kind of Fe containing amino acid3+The synthetic method of fluorescence probe prepares above-mentioned rhodamine B Fe3+Fluorescence probe,
Synthetic method is as follows：
Step 1：Among the bright B lactams of synthesizing rhodamine, 2g rhdamine Bs are weighed, are dissolved in alcohol solvent, then
Ethylenediamine solution is added dropwise in rhodamine B solution, is heated to 50 DEG C, back flow reaction 6h, solution is by jujube in reaction process
Red becomes orange-yellow, obtains rhodamine B lactam intermediate；
Step 2：Synthesize the Fe containing amino acid3+Fluorescence probe weighs 1mmol rhodamine B lactams, is dissolved in ethyl alcohol
1.2mmol serine solution is then added dropwise in rhodamine B lactams solution by solvent, is heated to 80 DEG C, reflux is thin
Analysis tracks to reaction and terminates layer by layer, obtains target compound by column chromatographic isolation and purification after reaction, column chromatography for separation is pure
It is 1 to change etoh solvent with methylene chloride volume ratio:200.
Example IV
A kind of Fe containing amino acid3+Fluorescence probe, synthesis group R1 are C2H5, group R2 and R3 be H, group R4 is CH3, n
For 2 rhodamine 6G Fe3+Fluorescence probe.
A kind of Fe containing amino acid3+The synthetic method of fluorescence probe prepares above-mentioned rhodamine 6G Fe3+Fluorescence probe,
Its synthetic method is as follows：
Step 1：Among the bright 6G lactams of synthesizing rhodamine, 2g rhodamine 6G dyestuffs are weighed, alcohol solvent is dissolved in, connects
And ethylenediamine solution be added dropwise in rhodamine 6G solution, be heated to 50 DEG C, back flow reaction 6h, in reaction process solution by
Purplish red becomes orange-yellow, obtains rhodamine 6G lactam intermediate；
Step 2：Synthesize the Fe containing amino acid3+Fluorescence probe weighs 1mmol rhodamine 6G lactams, is dissolved in ethyl alcohol
1.2mmol serine solution is then added dropwise in rhodamine 6G lactams solution by solvent, is heated to 80 DEG C, reflux is thin
Analysis tracks to reaction and terminates layer by layer, obtains target compound by column chromatographic isolation and purification after reaction, column chromatography for separation is pure
It is 1 to change etoh solvent with methylene chloride volume ratio:200.
Embodiment five
As shown in Fig. 2, being separately added into the K of 5 times of equivalents into probe solution+、Na+、Ca2+、Mg2+、Zn2+、Cd2+、Mn2+、
Cu2+、Pb2+When ion, probe solution is colourless, and fluorescence intensity does not also change at 580nm, it is seen that probe keeps former
The structure come, can be stable in the presence of in these solution systems.When Fe is added in probe solution3+Afterwards, solution becomes red from colourless
Color, fluorescence intensity is remarkably reinforced at 580nm, a strong emission peak occurs.This is because Fe3+With probe reaction so that Luo Dan
Bright loop coil is opened, and fluorescent emission is generated.
Embodiment six
As shown in figure 3, using the fluorescence intensity of maximum emission peak position as ordinate, metal ion is abscissa, past first
Interfering ion (the K of 5 times of equivalents is separately added into probe solution+、Na+、Ca2+、Mg2+、Zn2+、Cd2+、Mn2+、Cu2+、Pb2+), then
The Fe of 3 times of equivalents is added3+, solution immediately becomes red from colorless state, tests its fluorescence intensity, as seen from the figure, dry at other
In the presence of disturbing ion, probe is to Fe3+Still there is good recognition capability.
Embodiment seven
As shown in figure 4, preparing 5 μM of probe solutions of 15 parts of 5mL, it is separately added into 0-240 μM of iron ion, carries out fluorescence inspection
Survey (λEx=520nm), fluorescence intensity in each system is calculated, by analyzing fluorescence intensity and Fe at 580nm3+The relationship of concentration,
Probe is assessed to Fe3+Response performance, as seen from the figure with Fe3+The fluorescence intensity of the increase of concentration, solution gradually increases, directly
Do not changing to maximum emission intensity, probe is in Fe3+Concentration 5 × 10-6Mol/L~6 × 10-5It is linearly closed within the scope of mol/L
System, linearly dependent coefficient R2=0.9958, and probe is to Fe3+Detection be limited to 1.29 × 10-7mol/L。
Embodiment eight
As shown in figure 5, fixed 10 μM of concentration and probe concentration, is added the Fe of 2eq3+Solutions Solution becomes red from colourless, at 580nm
Fluorescence intensity be remarkably reinforced, display probe to Fe3+Response, continuously add the EDTA solution fluorescence remitted its furys of 5eq, this be by
In EDTA and Fe3+Complexing has seized the Fe that part is complexed with probe3+, continuously add the Fe of 2eq3+Afterwards, the fluorescence intensity of system
Enhance again, shows probe and Fe3+Combination be belong to corrdination type identification, and have invertibity.
The preferred embodiment of the present invention is above are only, but the design concept of the present invention is not limited thereto, all profits
The change for carrying out unsubstantiality to the present invention with this design, should all belong to the behavior for invading the scope of the present invention.
Claims (9)
1. a kind of Fe containing amino acid3+Fluorescence probe, it is characterised in that：Fe containing amino acid3+The following institute of fluorescence probe structural formula
Show：
2. the Fe containing amino acid according to claim 13+Fluorescence probe, it is characterised in that：The Fe containing amino acid3+Fluorescence
Group R1, R2, R3, R4 H or group R1 and R2 are CH in probe structure formula3, group R3 and R4 are H or group R1 and R2 are
C2H5, group R3 and R4 are H or group R1 is C2H5, group R2 and R3 be H, group R4 is CH3。
3. the Fe containing amino acid according to claim 13+Fluorescence probe, it is characterised in that：The Fe containing amino acid3+Fluorescence
N is 0,2,3 in probe structure formula ... n.
4. a kind of Fe containing amino acid3+The synthetic method of fluorescence probe, it is characterised in that：It prepares described in claim 1 containing ammonia
The Fe of base acid3+Fluorescence probe, synthetic method are as follows：
Step 1：The bright lactam intermediate of synthesizing rhodamine, weighs 2-3g rhodamines, is dissolved in organic solvent, then will
Aminated compounds solution is added dropwise in rhodamine solution, is heated to 50-60 DEG C, Luo Dan is obtained after back flow reaction 2-7h
Bright lactam intermediate；
Step 2：Synthesize the Fe containing amino acid3+Fluorescence probe weighs 1-2mmol rhodamine lactams, is dissolved in organic molten
Serine solution is then added dropwise in rhodamine lactams solution by agent, is heated to 60-85 DEG C, reflux, thin-layer chromatography with
Track to reaction terminates, and obtains target compound by column chromatographic isolation and purification after reaction.
5. the Fe containing amino acid according to claim 43+The synthetic method of fluorescence probe, it is characterised in that：It is described organic molten
Agent is methanol, ethyl alcohol, acetonitrile.
6. the Fe containing amino acid according to claim 43+The synthetic method of fluorescence probe, it is characterised in that：The rhodamine
The molar ratio of lactams and serine is 1:1.0-1.5.
7. the Fe containing amino acid according to claim 43+The synthetic method of fluorescence probe, it is characterised in that：The synthesis mesh
The reaction temperature for marking compound is 80 DEG C.
8. the Fe containing amino acid according to claim 43+The synthetic method of fluorescence probe, it is characterised in that：The column chromatography
It is dichloromethane and ethyl alcohol to isolate and purify solvent.
9. the Fe containing amino acid according to claim 43+The synthetic method of fluorescence probe, it is characterised in that：The column chromatography
The volume ratio for isolating and purifying methylene chloride and ethyl alcohol is 160-220:1.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113045591A (en) * | 2021-04-12 | 2021-06-29 | 延安大学 | Double-molecular rhodamine fluorescent probe R6G-PA and preparation method and application thereof |
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| CN113045591A (en) * | 2021-04-12 | 2021-06-29 | 延安大学 | Double-molecular rhodamine fluorescent probe R6G-PA and preparation method and application thereof |
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