Near-infrared fluorescent probe compound as well as preparation method and application thereof

A technology of fluorescent probes and compounds, which is applied in the field of single-charged nitrogen-containing cyanine fluorescent dyes and their preparation, can solve the problems that the spectrum is not in the near-infrared region and the equilibration time is long, and achieve wide application prospects, low biological toxicity, and good sensitivity Effect

Inactive Publication Date: 2013-04-24
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The second example is based on the fluorescein-based Tsuji-Trost allyl oxidative intercalation reactive palladium fluorescent probe, the biggest shortcoming of which is that the spectrum is not

Method used

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  • Near-infrared fluorescent probe compound as well as preparation method and application thereof
  • Near-infrared fluorescent probe compound as well as preparation method and application thereof
  • Near-infrared fluorescent probe compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 The synthetic route of the parent Cy7 dye VIa containing chlorine bridged ring

[0039]

[0040] (1) Synthesis of intermediate 2,3,3-trimethyl-3H-indoline

[0041] In a 1000mL three-neck flask, add 150mL of glacial acetic acid, 84mL (0.8mol) of 3-methyl-2-butanone and 0.26mol of p-hydrazinobenzene in sequence. The mixture was heated to reflux for 3 h, the reactant was poured into a beaker, and after standing for cooling, a pink solid precipitated out. Filter and dry in vacuo to obtain 2,3,3-trimethyl-3H-indoline with a yield of 75%.

[0042] (2) Synthesis of intermediate N-ethyl-2,3,3-trimethyl-3H-indoline

[0043] In a 100mL round bottom flask, add 15.9g (0.1mol) 2,3,3-trimethyl-3H-indoline, 23.4g (0.15mol) ethyl iodide, and 65mL toluene in sequence, and heat to reflux under nitrogen protection After reacting for 5 hours, a pink solid was obtained. Ultrasound made the solid on the wall enter the liquid, filtered, washed several times with ether, and dri...

Embodiment 2

[0048] Synthesis and characterization of embodiment 2 dye VIIa

[0049]

[0050] Dye VIa was pre-dried in vacuum at 50-60°C for 8h, nucleophile C 2 h 5 NH 2 Refined by vacuum distillation in advance. The glassware used was pre-dried at 120°C for 3 hours, and the three-necked round-bottom flask used was cooled under a nitrogen atmosphere, and 0.12 mmol of dye VIa and 1.2 mmol of nucleophile C were added. 2 h 5 NH 2 . Add about 15 mL of anhydrous DMF as solvent and 3 mmol of acid-binding agent DIEA with a syringe under nitrogen atmosphere. The reaction mixture was kept at 40-55° C. and stirred for 2 h under the protection of nitrogen. The reaction solution was poured into rapidly stirred 300mL ether, and a large amount of blue solid precipitated. Filter the filtrate with a sand core funnel, and dissolve the solid from the funnel with methanol, evaporate the methanol to dryness, and obtain the crude dye VIIa, which is then purified by column chromatography. 1HNMR (400...

Embodiment 3

[0051] Synthesis and characterization of embodiment 3 dye VIIIa

[0052]

[0053]Dye VIIa was vacuum-dried at 50-60°C for 8 h in advance, and the nucleophile allyl chloroformate was purified by distillation under reduced pressure. The glassware used was pre-dried at 120° C. for 3 h, and the three-necked round-bottom flask used was cooled under nitrogen atmosphere, and then 0.1 mmol of dye VIIa and 1 mmol of nucleophile allyl chloroformate were added. Under a nitrogen atmosphere, add about 10 mL of anhydrous dichloromethane as a solvent and 2.5 mmol of an acid-binding agent DIEA with a syringe. The reaction mixture was stirred at room temperature for 2 h under nitrogen protection. The reaction solution was poured into rapidly stirred ether, and a large amount of green solid precipitated. Filter the filtrate with a sand core funnel, and dissolve the solid from the funnel with methanol, evaporate the methanol to dryness, and obtain the crude dye VIIIa, which is then purified...

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Abstract

The invention relates to a near-infrared fluorescent probe compound. In a formula, X is C(CH3)2, O, S or Se, R1 and R2 are independently selected from C1-C18 alkyl or benzyl, R3 and R4 are H, SO3R6, CO2R7 or NCS, R5 is saturated or unsaturated straight-chain or branched-chain C1-C18 alkyl, hydroxy C1-C18 alkyl, hydroxy C1-C18 alkyl, amino C1-C18 alkyl, acyl, phenyl, naphthyl or benzyl and Y is an anion. The heptamethine cyanine probe compound I provided by the invention can be used for selectively detecting palladium ions and zero-valent palladium with the ppb-level concentration in environment and providing enhanced fluorescence signals and can be also used for analyzing the palladium in biological imaging and complex environments. A reducing agent used for detecting the zero-valent palladium is PEG which has better biocompatibility and lower toxicity as compared with the traditional reducing agent PPh3.

Description

technical field [0001] The invention relates to a new class of near-infrared fluorescent probes in the field of fine chemicals, a preparation method and applications thereof, in particular to a class of single-charged nitrogen-containing cyanine fluorescent dyes and a preparation method thereof. This type of compound is suitable for the detection of palladium ions in the field of fine chemical industry. Background technique [0002] Fluorescent molecular probes are a type of converter that can selectively convert the information of the analyzed object (such as acidity, concentration, chemical or biological activity, etc.) into a fluorescent signal that can be easily measured by analytical instruments, thereby realizing the analysis and detection of the analyte. Fluorescent molecular probes are usually composed of the following three parts: (1) the acceptor part (receptor) that recognizes the target, that is, the bonding group or the recognition group, its function is to bind...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09B23/10G01N21/64
Inventor 宋锋玲王君玉彭孝军
Owner DALIAN UNIV OF TECH
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