CN108484619A - A kind of rhodamine base Fe3+Fluorescence probe and preparation method thereof - Google Patents
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Abstract
The invention belongs to field of biological detection, and in particular to a kind of rhodamine base Fe3+Fluorescence probe and preparation method thereof, structural formula design a kind of rhodamine base Fe of special construction as shown, based on rhodamine and glucose with preferable water solubility3+Fluorescence probe.A certain amount of rhodamine lactams and 1,8 naphthalic anhydride derivatives occur condensation reaction and obtain rhodamine base Fe under certain condition3+Fluorescence probe, building-up process raw material is simple and easy to get, reaction condition is mild, easy to operate, and the probe is to Fe3+It has good selectivity, is not interfered by other metal ions, Fe in biological cell can be quickly detected under water environment3+, the probe and Fe3+Combination be belong to corrdination type identification, and have invertibity, Fe in biological cell can be quickly detected under water environment3+。
Description
Technical field
The invention belongs to field of biological detection, and in particular to a kind of rhodamine base Fe3+Fluorescence probe and preparation method thereof.
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.It is directed to ferro element in most cellular processes in human body, such as metabolism, the conjunction of electronics transfer and DNA
At.It is Fe that usual ferro element, which exists in human body with two kinds of ionic species,2+And Fe3+, two kinds of ion meetings in cellular physiological processes
In certain equilibrium state.Therefore the content of iron in cell, distribution and iron ion form must be controlled, if normal in human body
Ferro element operation destroyed, the unbalance of body will be caused, such as anaemia, hemochromatosis and senile dementia, therefore right
The detection of iron ion is of great significance.
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.Fluorescence method can using suitable probe
It is lossless to realize that efficient, " bore hole " detects to object, while qualitative and quantitative analysis is carried out to object.Have at present
The fluorogen of difference excitation and launch wavelength is used as the signal recipient of chemical detector, such as cumarin, pyrene, 1,8- naphthalenes two
Formamide, rhodamine, flower cyanines class, BODIPY classes etc..The fluorescence probe wherein built as fluorophor using rhodamine, due to its tool
There are excellent fluorescence property and good modifiability, has become one of fluorescence probe of greatest concern at present.
Rhodamine is a kind of fluorescent dye for belonging to xanthene class, and the following A of structure is oxygen anthracene heterocycle structure, and B is rhodamine
Dyestuff.Since it is with superior Photophysics, such as high molar extinction coefficient, good light stability, fluorescence quantum yield is high, hair
The advantages that ejected wave length is long so that it is widely used.Conjunction was reported for the first time from Noelting and Dziewonsky in 1905
At rhodamine compound (Noelting, E.；Dziewonski,K.To the knowledge of the
Rhodamine [J] .Ber.Dtsch Chem.Ges., 1905,38,3516-3527.), hereafter rhodamine compound is just wide
It is general to be applied to each field, but current rhodamine iron ion fluorescence is poor in the presence of water solubility, and synthesis step is cumbersome, sensitivity degree
It is low, the problems such as poor anti jamming capability.
As patent No. CN201610554440.0 discloses a kind of fluorescent probe compounds and its preparation method and application, institute
It is rhodamine hydrazide derivatives, the first bright hydrazine hydrate of synthesizing rhodamine, then synthesising probing needle molecule to state fluorescence probe；Probe molecule of the present invention
Raw material is easy to get, and synthetic route is simple, and post-processing is simple and convenient.Probe dissolubility in the mixed solution of second alcohol and water is preferable, most
Big launch wavelength is at 581nm, and fluorescence signal is weaker, and with the addition of ferric ion, probe molecule goes out at wavelength 581nm
Existing stronger emission peak.Therefore can be used for detecting the ferric ion in aqueous solution, this probe can be detected effectively in addition
Ferric ion in living cells, can be applied in biomedicine field, but the probe can be influenced by aluminum ions, resist
Interference performance is poor.
Patent No. CN102391150A provides a kind of iron-ion fluorescent probe compound p-phenylenediamine contracting ethyl diacetate base
Benzaldehyde and preparation method thereof, the compound show identity in buffer solution to iron ion, minimum detectable iron from
Son a concentration of 10-6Mol/L, but there are the fluorescence probes not to have linear rule, the survey of no standard measure to the response of iron ion
The concentration of iron ion is tried, and fluorescence probe detection minimum only has 10-6Mol/L cannot meet the test of lower iron concentration,
Its sensitivity is poor.
Patent No. CN201510013814.3 discloses a kind of ferric ion fluorescent probe compounds and its prepares and answer
With.The iron ion fluorescence probe preparation method is：Rhodamine B is mixed with anhydrous ethylenediamine, and reflux is made in ethanol
The amide of rhodamine；The hydroxyl that dinaphthol is protected with chloromethyl methyl ether, under the action of butyl lithium, with n,N-Dimethylformamide
After reaction, methyl ether methyl is sloughed with hydrochloric acid, obtains the dinaphthol with aldehyde radical；Finally by the amide of rhodamine and the connection for carrying aldehyde radical
Naphthols flows back in ethanol, and washing obtains the fluorescent probe compounds of pure ferric ion.The probe to ferric iron from
Son has good selectivity and sensitivity, and detection sample pre-treatments are simple, and do not have toxicity to cell, is used for water body environment
And the detection of the ferric ion in biological cell, but its synthesis step is cumbersome, the reaction time is long, the probe tetrahydrochysene
Furans dissolves, it is seen that its water solubility is poor, and tetrahydrofuran has certain toxicity to biological cell.
Therefore strongly professional in order to overcome analytical instrument expensive, it takes, there is destructiveness will also result in inspection simultaneously sample
That there are synthesis steps is cumbersome for the problems such as surveying the loss of object and fluorescence probe, and water-soluble poor, sensitivity degree is low, poor anti jamming capability
The problems such as, design synthesizes a kind of good water solubility, and specificity is strong, and the novel fluorescence probe of high sensitivity has great importance.
Invention content
In order to solve above-mentioned analytical instrument it is expensive, it is strongly professional, time-consuming, have destructive to sample while will also result in inspection
That there are synthesis steps is cumbersome for the problems such as surveying the loss of object and fluorescence probe, it is water-soluble it is poor, sensitivity degree is low, poor anti jamming capability
The problems such as, the present invention provides a kind of rhodamine base Fe3+Fluorescence probe and preparation method thereof.
A kind of rhodamine base Fe3+Fluorescence probe, structural formula are as shown in Figure 1.
Further, rhodamine base Fe3+Group R1, R2, R3, R4 H or group R1 and R2 are in fluorescence probe structural formula
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 be
H, group R4 is CH3。
Further, rhodamine base Fe3+N is 0,2,3 in fluorescence probe structural formula ... n.
A kind of rhodamine base Fe3+The synthetic method of fluorescence probe prepares above-mentioned rhodamine base Fe3+Fluorescence probe closes
It is as follows at method：
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 liquor, be heated to 50-65 DEG C, Luo Dan is obtained after back flow reaction 2-7h
Bright lactam intermediate；
Step 2：Synthesize 1,8- naphthalic anhydride derivatives：2-3g 1 is weighed, 8- naphthalic anhydrides carry out nitration reaction,
Then it carries out reduction reaction and obtains 4- amino -1,8- naphthalic anhydrides, by gained 4- amino -1,8- naphthalic anhydride and grape
Sugar carries out condensation reaction and obtains 1,8- naphthalic anhydride derivatives in organic solvent；
Step 3：The bright base Fe of synthesizing rhodamine3+Fluorescence probe weighs 1-2mmol rhodamine lactams, is dissolved in organic molten
1,8- naphthalic anhydride derivative solutions are then added dropwise in rhodamine lactams solution, are heated to 60-85 DEG C by agent,
Reflux, thin-layer chromatography, which tracks to reaction, to be terminated, and obtains rhodamine base Fe by column chromatographic isolation and purification after reaction3+Fluorescence is visited
Needle.
Further, organic solvent is methanol, ethyl alcohol, acetonitrile.
Further, the molar ratio of 4- amino -1,8- naphthalic anhydride and glucose is 1:1.0-2.0.
Further, the molar ratio of rhodamine lactams and 1,8- naphthalic anhydride derivatives is 1:1.0-1.5.
Further, column chromatographic isolation and purification solvent is dichloromethane and ethyl alcohol.
The present invention is based on rhodamines and glucose to have preferable water solubility, designs a kind of Luo Dan of special construction
Bright base Fe3+Fluorescence probe, a certain amount of rhodamine lactams and 1,8- naphthalic anhydride derivatives contract under certain condition
Rhodamine base Fe is obtained by the reaction in conjunction3+Fluorescence probe, building-up process raw material is simple and easy to get, and reaction condition is mild, easy to operate, described
Probe is to Fe3+It has good selectivity, is not interfered by other metal ions, it can the quickly detection life under water environment
The intracellular Fe of object3+, the probe and Fe3+Combination be belong to corrdination type identification, and have invertibity.
Description of the drawings
Fig. 1 is rhodamine base Fe3+The structural formula of fluorescence probe；
Fig. 2 is rhodamine base Fe3+Fluorescence emission spectrogram of compound of the fluorescence probe to metalloform-selective；
Fig. 3 is rhodamine base Fe3+Fluorescence probe is to different Fe3+The fluorescence emission spectrogram of compound of concentration；
Fig. 4 is rhodamine base Fe3+The fluorescence range of linearity of fluorescence probe；
Fig. 5 is rhodamine base Fe3+The fluorescence emission spectrogram of compound of fluorescence probe reversibility test.
Specific implementation mode
As shown in Figure 1, a kind of rhodamine base Fe3+Fluorescence probe, specific embodiment are as follows：
Embodiment one
A kind of rhodamine 110Fe3+Fluorescence probe, synthesis group R1, R2, R3, R4 H, the rhodamine 110Fe that n is 23+
Fluorescence probe.
A kind of rhodamine 110Fe3+The synthetic method of fluorescence probe prepares above-mentioned rhodamine 110Fe3+Fluorescence probe,
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 2：1,8- naphthalic anhydride derivatives are synthesized, 2g 1 is weighed, 8- naphthalic anhydrides carry out nitration reaction, connect
Carry out reduction reaction and obtain 4- amino -1,8- naphthalic anhydrides, by gained 1mol 4- amino -1,8- naphthalic anhydrides with
1.2mol glucose carries out condensation reaction in alcohol solvent and obtains 1,8- naphthalic anhydride derivatives；
Step 3：The bright 110Fe of synthesizing rhodamine3+Fluorescence probe weighs 110 lactams of 1mmol rhodamines, is dissolved in ethyl alcohol
Solvent, then by 1.2mmol 1,8- naphthalic anhydride derivative solutions are added dropwise in 110 lactams solution of rhodamine, are added
Heat is to 80 DEG C, and reflux, thin-layer chromatography, which tracks to reaction, to be terminated, and obtains target chemical combination by column chromatographic isolation and purification after reaction
Object, column chromatographic isolation and purification etoh solvent are 1 with methylene chloride volume ratio:200.
Embodiment two
A kind of tetramethylrhodamine Fe3+Fluorescence probe, synthesis group R1 and R2 are CH3, group R3 and R4 be H, n is 2
Tetramethylrhodamine Fe3+Fluorescence probe.
A kind of tetramethylrhodamine Fe3+The synthetic method of fluorescence probe prepares above-mentioned tetramethylrhodamine Fe3+Fluorescence
Probe, 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 2：1,8- naphthalic anhydride derivatives are synthesized, 2g 1 is weighed, 8- naphthalic anhydrides carry out nitration reaction, connect
Carry out reduction reaction and obtain 4- amino -1,8- naphthalic anhydrides, by gained 1mol 4- amino -1,8- naphthalic anhydrides with
1.2mol glucose carries out condensation reaction in alcohol solvent and obtains 1,8- naphthalic anhydride derivatives；
Step 3：Synthesize tetramethylrhodamine Fe3+Fluorescence probe weighs 1mmol tetramethylrhodamine lactams, its is molten
In alcohol solvent, then by 1.2mmol 1,8- naphthalic anhydride derivative solutions are added dropwise to tetramethylrhodamine lactams
In solution, 80 DEG C are heated to, reflux, thin-layer chromatography, which tracks to reaction, to be terminated, and is obtained after reaction by column chromatographic isolation and purification
To target compound, column chromatographic isolation and purification etoh solvent is 1 with methylene chloride volume ratio:200.
Embodiment three
A kind of rhodamine B Fe3+Fluorescence probe, synthesis group R1 and R2 are C2H5, group R3 and R4 be H, n be 2 sieve
Dan Mingji Fe3+Fluorescence probe.
A kind of rhodamine B Fe3+The synthetic method of fluorescence probe prepares above-mentioned rhodamine B Fe3+Fluorescence probe closes
It is as follows at method：
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 2：1,8- naphthalic anhydride derivatives are synthesized, 2g 1 is weighed, 8- naphthalic anhydrides carry out nitration reaction, connect
Carry out reduction reaction and obtain 4- amino -1,8- naphthalic anhydrides, by gained 1mol 4- amino -1,8- naphthalic anhydrides with
1.2mol glucose carries out condensation reaction in alcohol solvent and obtains 1,8- naphthalic anhydride derivatives；
Step 3：The bright B Fe of synthesizing rhodamine3+Fluorescence probe weighs 1mmol rhodamine B lactams, it is molten to be dissolved in ethyl alcohol
Agent, then by 1.2mmol 1,8- naphthalic anhydride derivative solutions are added dropwise in rhodamine B lactams solution, are heated to
80 DEG C, reflux, thin-layer chromatography, which tracks to reaction, to be terminated, and obtains target compound by column chromatographic isolation and purification after reaction,
Column chromatographic isolation and purification etoh solvent is 1 with methylene chloride volume ratio:200.
Example IV
A kind of rhodamine 6G Fe3+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 rhodamine 6G Fe3+The synthetic method of fluorescence probe prepares above-mentioned rhodamine 6G Fe3+Fluorescence probe,
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 2：1,8- naphthalic anhydride derivatives are synthesized, 2g 1 is weighed, 8- naphthalic anhydrides carry out nitration reaction, connect
Carry out reduction reaction and obtain 4- amino -1,8- naphthalic anhydrides, by gained 1mol 4- amino -1,8- naphthalic anhydrides with
1.2mol glucose carries out condensation reaction in alcohol solvent and obtains 1,8- naphthalic anhydride derivatives；
Step 3：The bright 6G Fe of synthesizing rhodamine3+Fluorescence probe weighs 1mmol rhodamine 6G lactams, is dissolved in ethyl alcohol
Solvent, then by 1.2mmol 1,8- naphthalic anhydride derivative solutions are added dropwise in rhodamine 6G lactams solution, add
Heat is to 80 DEG C, and reflux, thin-layer chromatography, which tracks to reaction, to be terminated, and obtains target chemical combination by column chromatographic isolation and purification after reaction
Object, column chromatographic isolation and purification etoh solvent are 1 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 and Figure 4,5 μM of probe solutions for preparing 16 parts of 5mL, are separately added into 0-240 μM of iron ion, carry out
Fluoroscopic examination (λEx=520nm), fluorescence intensity in each system is calculated, by analyzing fluorescence intensity and Fe at 580nm3+Concentration
Relationship, assessment probe to Fe3+Response performance.Fig. 3 shows with Fe3+The fluorescence intensity of the increase of concentration, solution gradually increases
By force, until maximum emission intensity is not changing.Fig. 4 shows probe in Fe3+Concentration 4 × 10-6Mol/L~6 × 10-5Mol/L ranges
It is interior in a linear relationship, linearly dependent coefficient R2=0.9964, and probe is to Fe3+Detection be limited to 1.29 × 10-7mol/L。
Embodiment seven
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 adds the EDTA solution fluorescence remitted its furys of 5eq, this is
Due to EDTA and complexing, the Fe that part is complexed with probe has been seized3+, continuously add the Fe of 2eq3+Afterwards, the fluorescence intensity of system is again
Enhancing, 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 (8)
1. a kind of rhodamine base Fe3+Fluorescence probe, it is characterised in that：Rhodamine base Fe3+Fluorescence probe structural formula is as follows：
2. rhodamine base Fe according to claim 13+Fluorescence probe, it is characterised in that：The rhodamine base Fe3+Fluorescence probe
Group R1, R2, R3, R4 H or group R1 and R2 are CH in structural formula3, group R3 and R4 are H or group R1 and R2 are C2H5、
Group R3 and R4 is H or group R1 is C2H5, group R2 and R3 be H, group R4 is CH3。
3. rhodamine base Fe according to claim 13+Fluorescence probe, it is characterised in that：The rhodamine base Fe3+Fluorescence probe
N is 0,2,3 in structural formula ... n.
4. a kind of rhodamine base Fe3+The synthetic method of fluorescence probe, which is characterized in that prepare rhodamine described in claim 1
Base Fe3+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 2：1,8- naphthalic anhydride derivatives are synthesized, 2-3g 1 is weighed, 8- naphthalic anhydrides carry out nitration reaction, then
It carries out reduction reaction and obtains 4- amino -1,8- naphthalic anhydrides, gained 4- amino -1,8- naphthalic anhydride is being had with glucose
Condensation reaction is carried out in solvent obtains 1,8- naphthalic anhydride derivatives；
Step 3：The bright base Fe of synthesizing rhodamine3+Fluorescence probe weighs 1-2mmol rhodamine lactams, is dissolved in organic solvent,
Then 1,8- naphthalic anhydride derivative solutions are added dropwise in rhodamine lactams solution, are heated to 60-85 DEG C, returned
Stream, thin-layer chromatography, which tracks to reaction, to be terminated, and obtains target compound by column chromatographic isolation and purification after reaction.
5. rhodamine base Fe according to claim 43+The synthetic method of fluorescence probe, it is characterised in that：The organic solvent
For methanol, ethyl alcohol, acetonitrile.
6. rhodamine base Fe according to claim 43+The synthetic method of fluorescence probe, it is characterised in that：In the rhodamine
The molar ratio of amide and 1,8- naphthalic anhydride derivatives is 1:1.0-1.5.
7. rhodamine base Fe according to claim 43+The synthetic method of fluorescence probe, it is characterised in that：Amino -1 4-,
The molar ratio of 8- naphthalic anhydrides and glucose is 1:1.0-2.0.
8. rhodamine base Fe according to claim 43+The synthetic method of fluorescence probe, it is characterised in that：The column chromatography point
It is dichloromethane and ethyl alcohol from purification solvent.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109490267A (en) * | 2018-11-23 | 2019-03-19 | 西北师范大学 | It is enclosed with application of the UiO-66 of rhodamine 6G in fluorescence detection iron ion |
| CN114106004A (en) * | 2021-11-30 | 2022-03-01 | 福建师范大学 | Chelate zinc ion fluorescent probe and preparation method and biological application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110008970A (en) * | 2009-07-21 | 2011-01-27 | 포항공과대학교 산학협력단 | Rhodamin b derivative compound as the fluorigenic and chromogenic probe for ag+/ag nanoparticles in aqueous media |
| CN103524516A (en) * | 2013-09-11 | 2014-01-22 | 江南大学 | Novel rhodamine fluorescence probe |
| CN104936966A (en) * | 2012-10-29 | 2015-09-23 | 布约迪姆实验室 | New antibacterial compounds and biological applications thereof |
-
2018
- 2018-04-26 CN CN201810387044.2A patent/CN108484619A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110008970A (en) * | 2009-07-21 | 2011-01-27 | 포항공과대학교 산학협력단 | Rhodamin b derivative compound as the fluorigenic and chromogenic probe for ag+/ag nanoparticles in aqueous media |
| CN104936966A (en) * | 2012-10-29 | 2015-09-23 | 布约迪姆实验室 | New antibacterial compounds and biological applications thereof |
| CN103524516A (en) * | 2013-09-11 | 2014-01-22 | 江南大学 | Novel rhodamine fluorescence probe |
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| CN109490267A (en) * | 2018-11-23 | 2019-03-19 | 西北师范大学 | It is enclosed with application of the UiO-66 of rhodamine 6G in fluorescence detection iron ion |
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