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Lysosome targeting fluorescent probe and synthesis method and cell imaging application thereof

A technology of fluorescent probes and synthesis methods, applied in the field of fluorescent probes, can solve the problems of low penetration depth, poor photostability, poor water solubility, etc., and achieve the effect of high spatial resolution and low background signal

Active Publication Date: 2021-06-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, most of the current commercial probes are excited by visible light or ultraviolet light, which have disadvantages such as low penetration depth, pH sensitivity, poor water solubility and poor photostability, which severely limit

Method used

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  • Lysosome targeting fluorescent probe and synthesis method and cell imaging application thereof
  • Lysosome targeting fluorescent probe and synthesis method and cell imaging application thereof
  • Lysosome targeting fluorescent probe and synthesis method and cell imaging application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of lysosomal probe N-2-morpholinoethyl-1,8-naphthalimide (Lyso-405).

[0041] Synthesis of intermediate N-(2-morpholinyl)ethyl-1,8-naphthalimide (Lyso-Br):

[0042]

[0043] Dissolve 4-bromo-1,8-naphthalene anhydride (277.07mg, 1.00mmol) in 13.85mL ethanol, then add 0.03mL (0.21mmol) N-(2-aminoethyl)morpholine to the reaction solution . The reaction solution was heated to 60°C and stirred for 0.5h. After cooling down, the off-white solid was filtered with suction and washed with ethanol, and dried in vacuo to obtain 56.40 mg of N-(2-morpholinyl)ethyl-1,8-naphthoimide with a yield of 69%.

[0044] 1 H NMR (400MHz, CDCl 3 )δ8.65(d, J=8.0Hz, 1H), 8.58(d, J=8.0Hz, 1H), 8.11(d, J=8.0Hz, 1H), 8.05(d, J=8.0Hz, 1H) ,7.86(t,J=8.0Hz,1H),4.34(t,J=7.2Hz,2H),3.68(br,4H),2.72(br,2H),2.60(br,4H).

[0045] Synthesis of Probe N-2-Morpholinylethyl-1,8-Naphthimide (Lyso-405)

[0046]

[0047] N-(2-morpholinyl)ethyl-1,8-naphthalimide (50.60mg, 0.13mmol), 2-azetidinon...

Embodiment 2

[0053] Synthesis of lysosomal probe N-2-morpholinoethyl-1,8-naphthalimide (Lyso-405).

[0054] Synthesis of intermediate N-(2-morpholinyl)ethyl-1,8-naphthalimide (Lyso-Br):

[0055]

[0056] Dissolve 4-bromo-1,8-naphthalene anhydride (277.07mg, 1.00mmol) in 22.17mL ethanol, then add 0.084mL (0.64mmol) N-(2-aminoethyl)morpholine to the reaction solution . The reaction solution was heated to 100°C and stirred for 2h. After cooling down, the off-white solid was suction-filtered and washed with ethanol, and dried in vacuo to obtain 164.41 mg of N-(2-morpholinyl)ethyl-1,8-naphthoimide with a yield of 66%.

[0057] Synthesis of Probe N-2-Morpholinylethyl-1,8-Naphthimide (Lyso-405)

[0058]

[0059] N-(2-morpholinyl)ethyl-1,8-naphthalimide (50.60mg, 0.13mmol), 2-azetidinone (35.42mg, 0.50mmol), Cs 2 CO 3 (162.91mg, 0.50mmol), G3-Xantphos (XantPhos Pd G3 95%) (1mol%) was placed in a two-necked bottle and replaced with nitrogen 3-4 times. Add 4.05 mL of dry dioxane to the r...

Embodiment 3

[0062] Synthesis of lysosomal probe N-2-morpholinoethyl-1,8-naphthalimide (Lyso-405).

[0063] Intermediate N-(2-morpholinyl)ethyl-1,8-naphthalimide (Lyso-Br):

[0064]

[0065] Dissolve 4-bromo-1,8-naphthalene anhydride (277.07mg, 1.00mmol) in 30.48mL ethanol, then add 0.14mL (1.06mmol) N-(2-aminoethyl)morpholine to the reaction solution . The reaction solution was heated to 140°C and stirred for 4h. After cooling down, the off-white solid was suction-filtered and washed with ethanol, and dried in vacuo to obtain 284.15 mg of N-(2-morpholinyl)ethyl-1,8-naphthoimide with a yield of 73%.

[0066] Synthesis of Probe N-2-Morpholinylethyl-1,8-Naphthimide (Lyso-405)

[0067]

[0068] N-(2-morpholinyl)ethyl-1,8-naphthalimide (50.60mg, 0.13mmol), 2-azetidinone (50.60mg, 0.71mmol), Cs 2 CO 3 (231.33 mg, 0.71 mmol), G3-Xantphos (XantPhos Pd G3 95%) (1 mol%) was placed in a two-necked bottle and replaced with nitrogen 3-4 times. 5.06 mL of dry dioxane was added to the reacti...

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Abstract

The invention provides a lysosome targeting fluorescent probe and a synthesis method and cell imaging application thereof. The fluorescent probe takes naphthalimide as a parent, an azacyclo-ketone substituent is introduced to the 4 site, an N-(2-aminoethyl) morpholine substituent is introduced to the N site, lysosome can be rapidly and accurately marked, the fluorescent probe is shown in the formula (1), R is the azacyclo-ketone substituent, and azacyclo-rings comprise a quaternary azacyclo-ring, a five-membered azacyclo-ring, a six-membered azacyclo-ring and the like. The excitation energy required by fluorescence emission of the probe is relatively low, and the probe can be used for labeling lysosome in living cells and performing two-photon fluorescence imaging at low concentration. And the fluorescent probe can penetrate deep tissues in two-photon fluorescence imaging, so that the probe can become a powerful tool for studying life processes such as lysosome transportation.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to a fluorescent probe for lysosome targeting, a synthesis method thereof and cell imaging applications. Background technique [0002] Lysosomes are vesicular organelles with a diameter of about 500nm surrounded by a single membrane and contain a variety of acid hydrolases, which can participate in many physiological processes, such as bone and tissue remodeling, plasma membrane repair, cholesterol homeostasis, and cellular death and cell signaling, etc. Furthermore, tumor invasion and metastasis are largely associated with altered lysosomal trafficking, expression and activity of lysosomal enzymes. Therefore, fluorescent labeling of lysosomes in living cells is of great significance for studying the transport mode of lysosomes and their role in tumor invasion. [0003] However, most of the current commercial probes are excited by visible light or ultraviole...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C09K11/06G01N21/64
CPCC07D401/04C09K11/06G01N21/6428G01N21/6456G01N21/6486C09K2211/1033C09K2211/1029
Inventor 徐兆超王光英乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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