CN110041723A - The fluorescent dye and preparation method thereof of near-infrared the second window excitation/emission - Google Patents
The fluorescent dye and preparation method thereof of near-infrared the second window excitation/emission Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/16—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms
- C09B23/162—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms
- C09B23/166—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms containing two or more nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The invention belongs to technical field of biological materials, the specially fluorescent dye and preparation method thereof of the second window of near-infrared excitation/emission.The fluorescent dye of near-infrared the second window excitation/emission of the invention is the seven methine cyanine dyes fluorescent dye of small organic molecule with general formula FD fluorescent dye structure.The dye fluorescence contains active group, such as amino, carboxyl, azido group, maleimide base group, succinimide group etc., it can modify on specific protein, polypeptide or DNA, form biomarker, to realize the targeted imaging to organism privileged site or the detection to specific molecular.
Description
Technical field
Technical field of biological materials of the present invention, and in particular to the fluorescent dye of a kind of the second window of near-infrared excitation/emission
And preparation method thereof.
Background technique
Molecular image technology such as Tomography (CT) common at present, ultrasonic imaging (US) and magnetic resonance imaging
(MRI) it is used for clinical treatment diagnosis.But these imaging techniques have the shortcomings that it is corresponding, can not if spatial resolution is poor
Real time monitoring, contrast agent can not function dough etc..Fluorescence imaging have in real time, Noninvasive, required sample size be few, high-resolution
The advantages that, it has been widely used in fields such as life science, clinical treatment diagnosis and fluoroimmunoassay detections.Currently, grinding
The persons of studying carefully just are focusing on the bioluminescence imaging and detection in the second window of near-infrared (1000nm~1700nm), this is because phase
For Visible-to-Near InfaRed first window (400~900nm), biological tissue in this wave band itself absorption and scatter weaker, meeting
Greatly improve image quality and penetration depth.
So it is current research that exploitation excitation wavelength and launch wavelength, which are all located at the fluorescent dye of the second window of near-infrared,
Emphasis.Currently, inorganic material such as rare earth nanometer particle, quantum dot, carbon nanotube can be realized the hair of the second window region of near-infrared
It penetrates, but their launch wavelength is all located in near-infrared first window, has potential biology containing heavy metal element simultaneously
Toxicity, into living body after be metabolized slowly, and dissolubility is poor in water, and which greatly limits their biologic applications values.Relatively
In inorganic material, organic fluorescent dye is easy to be metabolized because its relative molecular weight is smaller, it is easier to the advantages such as clinic conversion,
Cause the extensive concern of researchers.Cyanine fluorochrome is as a member in fluorescent dye in biomarker (DNA and albumen
The label of matter), have the advantages that its is protruded in terms of living cells and living tissue imaging applications, as molar extinction coefficient is big, maximum
Absorption and launch wavelength can increase with the extension of conjugated chain.The cyanine type dye of clinical approval only has indocyanine green at present
(ICG), but the absorption maximum of its molecule and launch wavelength are respectively positioned in near-infrared first window, while molecule can not carry out biology
Label.Meanwhile polymethin cyanine dyestuff is typically all symmetrical structure, lacks the active site of single fluorescent marker reaction.?
When fluorescent biolabels, fluorescent dye preferably in the molecule containing a single activable group (such as amino, carboxyl),
Ideal fluorescent probe molecule is obtained for specific derivatization reaction.And in order to obtain in this way containing more first of single-activity group
River cyanine dyes usually synthesizes asymmetric cyanine type dye, introduces an active group in one end of molecule.But this method
So that the synthesis of dyestuff and separating-purifying become complicated and difficult.Therefore, the present invention develops absorption maximum and launch wavelength is equal
Positioned at the cyanine type dye of the second window of near-infrared, while reactivity site is introduced in its symmetrical structure, be easy to the life in later period
Substance markers.
Summary of the invention
The purpose of the present invention is for the problem that current cyanine type dye absorb and launch wavelength it is shorter, be not easy biomarker,
There is provided that a kind of preparation process is simple, good biocompatibility, photostability is high, is easy to the second window of near-infrared of later period biomarker
Excitation and the fluorescent dye of transmitting and its preparation method and application.
The fluorescent dye of the second window of the near-infrared excitation and transmitting provided by the present invention for being easy to biomarker, is organic
Seven methine cyanine dyes fluorescent dye of small molecule, is denoted as FD dyestuff, reactivity site is introduced in its symmetrical structure, after being easy to
The biomarker of phase.Its chemical combination general structure is as follows:
Wherein:
R1And R2It is each independently selected from (CH2)nR8、(CH2)mOR9、(CHR10CH2O)pR9Or CH2C6H4R8；
R3、R4And R8It is each independently selected from as H, Cl, SO3R11Or COOR12；
R5For OR15、SR16Or NHR17；
R9For H or C1-18Alkyl；
R10For H or CH3；
R11For H or M；M=Na, K, N (R13、R14)；
R12For H, M, R6、R7、NH(CH2)yR18Or C1-18Alkyl；
R13、R14For H, C1-18Alkyl, (CH2)mOR9Or (CHR10CH2O)pR9；
R15、R16、R17For R1、C6H4(CH2)sCOR19Or (CH2)tCOR19；
R18For H, R6、R7、N3；
R19For OR12；
Y-For halogen anion or OTs-；
N, m, p, s, t, y are the integer of 0-18.
Term used in the present invention " alkyl " includes straight chained alkyl and branched alkyl；Term " halogen " includes fluorine, chlorine, bromine
And iodine；OTs-Refer to p-methyl benzenesulfonic acid radical ion.
The effect of substituent group is to adjust dyestuff in organic solvent or aqueous solution on the precursor structure of the compound of the present invention
In dissolubility.Wherein preferred R1And R2It is each independently selected from (CH2)nR10。
In the compounds of this invention, preferably R3And R4It is each independently selected from H or Cl.
In the compounds of this invention, preferably R5Selected from OR15、SR16Or NHR17。
In the compounds of this invention, most preferably, R1And R2Selected from CH3、(CH2)3SO3, R3And R4Selected from H, R5For
OC6H4CH2COOH or OC6H4CH2COOR6；As following compound FD-1, FD-2, FD-3 and FD-4:
The present invention also provides the preparation method of the fluorescent dye of the excitation of above-mentioned the second window of near-infrared and transmitting, specific steps
It is as follows:
(1) it is connected with substituent R3Or R4Naphthalene lactim and sultones or R1Or R2CH2Z, which reacts, is made chemical compounds I,
Reaction equation is shown in following formula:
Wherein or OTs, reaction temperature are 80~140 DEG C, and the reaction time is 4~18 hours, and reaction dissolvent is selected from N- first
Base -2-Pyrrolidone, toluene or n,N-Dimethylformamide, alkali compounds are sodium hydride, hydrofining, sodium hydroxide, hydrogen-oxygen
Change potassium or cesium hydroxide；Benzazolyl compounds, sultones or R1Or R2CH2The molar ratio of Z and alkali compounds is 1:1.1:
2~1:1.5:3 (i.e. 1:(1.1~1.5): (2~3)).
(2) chemical compounds I is reacted with Grignard Reagent MeMgZ generates compound ii, and reaction equation is shown in following formula:
Wherein, Z is halogen, and reaction temperature is 0~80 DEG C, and the reaction time is 0.1~5 hour, and reaction dissolvent is selected from tetrahydro
Furans, acetonitrile or ethyl alcohol；Chemical compounds I and the molar ratio of Grignard Reagent are 1:3~1:5 (i.e. 1:(3~5)).
(3) compound ii is reacted with condensing agent III generates compound FD dyestuff, and reaction equation is shown in following formula:
Wherein, reaction dissolvent is acetic anhydride, and catalyst is sodium acetate, and reaction temperature is 20~140 DEG C, the reaction time 1
~5 hours；Molar ratio 1:0.9:0.45~1:1.2:0.55 (i.e. 1:(0.9 of compound ii and sodium acetate and condensing agent III
~1.2): (0.45~0.55)).
(4) object FD and HOR are closed13、HSR14Or NH2R15Reaction generates compound FD-O, FD-S or FD-N, and reaction equation is
Shown in following formula:
Wherein, reaction dissolvent is n,N-Dimethylformamide, ethyl alcohol, methanol or acetonitrile, and reaction temperature is 20~60 DEG C, instead
It is 0.2~4 hour between seasonable, triethylamine, ammonium hydroxide is as catalyst or alkali compounds is not added.Compound FD and HOR13、HSR14
Or NH2R15Molar ratio 1:0.9~1:5 (i.e. 1:(0.9~5)).
The fluorescent dye of the second window of near-infrared excitation and transmitting provided by the invention, it is specific to can be used for organism blood vessel etc.
The targeted imaging at position or detection to specific molecular, and it is easy to biomarker.Since it contains active group, such as ammonia
Base, carboxyl, azido group, maleimide base group, succinimide group etc. can modify specific protein, polypeptide or DNA
On, biomarker is formed, to realize the targeted imaging to organism privileged site or the detection to specific molecular.
Specific embodiment
Embodiment 1:
The preparation of seven methine cyanines fluorescence probe FD dyestuffs.Specific step is as follows.
(1) synthesis of compound 1
It weighs naphthalene lactim (170mg, 1mmol) and sodium hydride (84mg, 2mmol) and is dissolved in 5mL N, N- dimethyl formyl
In solution, 15min is stirred at room temperature in amine, and iodoethane (171mg, 1.1mmol) then is added, and temperature rises to 80 DEG C, reacts 12h, cold
But to being spin-dried for after room temperature, column is crossed, compound 1 (184mg, 94%) is obtained.
(2) synthesis of compound 2
10mL N- methyl -2- pyrrole is added in naphthalene lactim (170mg, 1mmol) and potassium hydroxide (125mg, 2mmol)
In pyrrolidone, 30min is stirred at room temperature, butyl sultone (153mg, 1.1mmol) then is added, is heated to 90 DEG C, reacts 12h,
Acetone is added after being cooled to room temperature, filters to obtain compound 2 (317mg, 96%).
(3) synthesis of compound 3
Compound 2 (300mg, 1mmol) and tetrabutylammonium chloride (275mg, 1.1mmol) is dissolved in 4mL acetic acid, 90 DEG C
Lower reaction 0.5h, is added ethyl acetate, and filtering is spin-dried for, obtains yellow oily liquid, i.e. compound 3 (516mg, 85%).
(4) synthesis of compound 4 or 5
Weigh Compound 1 or 3 (1mmol) is dissolved in 10mL anhydrous tetrahydro furan (THF), under nitrogen protection, first is added
Base magnesium chloride (THF of 3.0M), 4.5mmol), dilute hydrochloric acid is then added in 60 DEG C of reaction 1h, generates precipitating, filters to obtain compound 4
Or 5.
The synthesis of (5) seven methine cyanine dyes 6 and 7
By compound 4 or 5 (1mmol), 20mL acetic anhydride is dissolved in condensing agent III (0.5mmol) and sodium acetate (1mmol)
In, 110 degree of lower reaction 2h are spin-dried for, column chromatography for separation obtains black solid i.e. compound 6 or 7.
The synthesis of (6) seven methine cyanine dye FD-1 and FD-2
By compound 6 or 7 (1mmol), it is dissolved in 10mL n,N-Dimethylformamide with p-hydroxyphenylaceticacid (5mmol),
60 degree of lower reaction 2h, are spin-dried for, column chromatography for separation obtains solid i.e. compound FD-1 or FD-2.
The synthesis of (7) seven methine cyanine dye FD-3 and FD-4
By compound FD-1 or FD-2 (1mmol), 10mL N, N- diformazan are dissolved in n-hydroxysuccinimide (5mmol)
In base formamide, 25 degree of lower reaction 2h are spin-dried for, column chromatography for separation obtains solid i.e. compound FD-3 or FD-4.
Claims (6)
1. a kind of fluorescent dye of the second window of near-infrared excitation/emission is seven methine cyanine dyes fluorescent dye of small organic molecule,
It is denoted as FD dyestuff, reactivity site is introduced in symmetrical structure, is easy to the biomarker in later period；Its chemical combination general structure is such as
Under:
Wherein:
R1And R2It is each independently selected from (CH2)nR8、(CH2)mOR9、(CHR10CH2O)pR9Or CH2C6H4R8；
R3、R4And R8It is each independently selected from as H, Cl, SO3R11Or COOR12；
R5For OR15、SR16Or NHR17；
R9For H or C1-18Alkyl；
R10For H or CH3；
R11For H or M; M=Na,K,N(R13、R14)；
R12For H, M, R6、R7、NH(CH2)yR18Or C1-18Alkyl；
R13、R14For H, C1-18Alkyl, (CH2)mOR9Or (CHR10CH2O)pR9；
R15、R16、R17For R1、C6H4(CH2)sCOR19Or (CH2)tCOR19；
R18For H, R6、R7、N3；
R19For OR12；
Y-For halogen anion or OTs-；
N, m, p, s, t, y are the integer of 0-18.
2. the fluorescent dye of the second window of near-infrared excitation/emission as described in claim 1, which is characterized in that R1、R2Respectively solely
It is vertical to be selected from (CH2)nR8。
3. the fluorescent dye of the second window of near-infrared excitation/emission as claimed in claim 2, which is characterized in that R3And R4Respectively solely
It is vertical to be selected from H or Cl.
4. the fluorescent dye of the second window of near-infrared excitation/emission as claimed in claim 13, which is characterized in that R5It is selected from
OR15、SR16Or NHR17。
5. the fluorescent dye of the second window of near-infrared excitation/emission as described in claim 1, which is characterized in that R1And R2It is selected from
CH3、(CH2)3SO3, R3And R4Selected from H, R5For OC6H4CH2COOH or OC6H4CH2COOR6, the compound FD- of as following structures
1, FD-2, FD-3 and FD-4:
。
6. a kind of preparation method of the fluorescent dye such as claim 1 near-infrared the second window excitation/emission, feature exist
In, the specific steps are as follows:
(1) it is connected with substituent R3Or R4Naphthalene lactim and sultones or R1Or R2CH2Z, which reacts, is made chemical compounds I, reaction
Formula is shown in following formula:
Wherein or OTs, reaction temperature are 80 ~ 140 DEG C, and the reaction time is 4 ~ 18 hours, and reaction dissolvent is selected from N- first
Base -2-Pyrrolidone, toluene or n,N-Dimethylformamide, alkali compounds are sodium hydride, hydrofining, sodium hydroxide, hydrogen-oxygen
Change potassium or cesium hydroxide；Benzazolyl compounds, sultones or R1Or R2CH2The molar ratio of Z and alkali compounds is 1:1.1:
2~1:1.5:3 ；
(2) chemical compounds I is reacted with Grignard Reagent MeMgZ generates compound ii, and reaction equation is shown in following formula:
Wherein, Z is halogen, and reaction temperature is 0 ~ 80 DEG C, and the reaction time is 0.1 ~ 5 hour, and reaction dissolvent is selected from tetrahydro furan
It mutters, acetonitrile or ethyl alcohol；Chemical compounds I and the molar ratio of Grignard Reagent are 1:3 ~ 1:5；
(3) compound ii is reacted with condensing agent III generates compound FD dyestuff, and reaction equation is shown in following formula:
Wherein, reaction dissolvent is acetic anhydride, and catalyst is sodium acetate, and reaction temperature is 20 ~ 140 DEG C, and the reaction time is 1 ~ 5
Hour；Molar ratio 1:0.9:0.45 ~ 1:1.2:0.55 of compound ii and sodium acetate and condensing agent III；
(4) object FD and HOR are closed13、HSR14Or NH2R15Reaction generates compound FD-O, FD-S or FD-N, and reaction equation is following formula institute
Show:
Wherein, reaction dissolvent is n,N-Dimethylformamide, ethyl alcohol, methanol or acetonitrile, and reaction temperature is 20 ~ 60 DEG C, reaction
Time is 0.2 ~ 4 hour, and as catalyst or alkali compounds is not added in triethylamine, ammonium hydroxide；Compound FD and HOR13、HSR14
Or NH2R15Molar ratio 1:0.9 ~ 1:5.
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Cited By (5)
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| CN110642839A (en) * | 2019-08-14 | 2020-01-03 | 深圳大学 | Nano probe and preparation method and application thereof |
| CN111187413A (en) * | 2020-01-10 | 2020-05-22 | 东华大学 | Sulfonated polyethyleneimine, nanofiltration membrane and preparation method thereof |
| CN112759946A (en) * | 2020-12-31 | 2021-05-07 | 上海戎科特种装备有限公司 | 1064nm laser absorption dye, preparation method thereof and optical-infrared-laser compatible stealth coating |
| CN112876873A (en) * | 2021-02-03 | 2021-06-01 | 中国科学技术大学 | Near-infrared two-region heptamethine cyanine dye and preparation method thereof |
| CN114644920A (en) * | 2022-02-14 | 2022-06-21 | 深圳大学 | Nano probe with self-detection function, preparation method and biomedical application thereof |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110642839A (en) * | 2019-08-14 | 2020-01-03 | 深圳大学 | Nano probe and preparation method and application thereof |
| CN110642839B (en) * | 2019-08-14 | 2022-04-01 | 深圳大学 | Nano probe and preparation method and application thereof |
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| CN111187413B (en) * | 2020-01-10 | 2021-03-23 | 东华大学 | Sulfonated polyethyleneimine, nanofiltration membrane and preparation method thereof |
| CN112759946A (en) * | 2020-12-31 | 2021-05-07 | 上海戎科特种装备有限公司 | 1064nm laser absorption dye, preparation method thereof and optical-infrared-laser compatible stealth coating |
| CN112876873A (en) * | 2021-02-03 | 2021-06-01 | 中国科学技术大学 | Near-infrared two-region heptamethine cyanine dye and preparation method thereof |
| CN112876873B (en) * | 2021-02-03 | 2022-01-11 | 中国科学技术大学 | Near-infrared two-region heptamethine cyanine dye and preparation method thereof |
| CN114644920A (en) * | 2022-02-14 | 2022-06-21 | 深圳大学 | Nano probe with self-detection function, preparation method and biomedical application thereof |
| CN114644920B (en) * | 2022-02-14 | 2023-10-27 | 深圳大学 | Nanometer probe with self-detection function, preparation method thereof and biomedical application |
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