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Lipid droplet targeting and biological thiol sensitive fluorescent probe for cancer cell tissue diagnosis and preparation and application thereof

A technology for fluorescent probes and cancer cells, applied in the field of organic fluorescent probes and fluorescent probes, can solve problems such as the connection that has not yet been reported, and achieve the effects of superior LDs targeting ability, concise synthesis route, and simple operation.

Active Publication Date: 2022-05-27
JILIN INST OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the recently reported LDs-targeting probes focus on monitoring the dynamic movement or polarity changes of LDs, while only limited studies involve the detection of reactive sulfur species in LDs, such as sulfur dioxide (SO 2 ) derivatives, hydrogen sulfide (H 2 S) and cysteine ​​(Cys)
More importantly, the levels of biothiols (i.e., cysteine ​​(Cys), homocysteine ​​(Hcy), glutathione (GSH) and hydrogen sulfide (H 2 The link between S)) and tumors has not been reported

Method used

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  • Lipid droplet targeting and biological thiol sensitive fluorescent probe for cancer cell tissue diagnosis and preparation and application thereof
  • Lipid droplet targeting and biological thiol sensitive fluorescent probe for cancer cell tissue diagnosis and preparation and application thereof
  • Lipid droplet targeting and biological thiol sensitive fluorescent probe for cancer cell tissue diagnosis and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Preparation of lipid droplet targeting and biothiol-sensitive fluorescent probes for cancer cell tissue diagnosis

[0040] A method for preparing a lipid droplet-targeted and biologically thiol-sensitive fluorescent probe for cancer cell tissue diagnosis. The synthetic route is as follows figure 2 As shown, the specific synthesis steps are:

[0041] Step S1, compound 1 (20 mg, 0.10 mmol) was dissolved in DCM (1 mL) at 0°C, compound 2 (40 mg, 0.15 mmol) was added, followed by Et 3 N (24 μL, 0.16 mmol); the resulting solution was stirred at room temperature overnight; the solvent was then concentrated in vacuo and the residue was purified using silica gel chromatography (PE / EtOAc, 5:1, v / v) to give compound 3 as a red solid ( 25mg, 60%). 1 H NMR (400MHz, CDCl 3 )δ9.71(s,1H),8.66(d,J=2.4Hz,1H),8.54(dd,J=8.8,2.4Hz,1H),8.36(d,J=8.8Hz,1H),7.68( d,J=9.2Hz,1H),6.63(dd,J=8.8,2.4Hz,1H),6.52(d,J=2.8Hz,1H),3.43(q,J=7.2Hz,4H),1.22( t,J=7.2Hz,6H). 13 C NMR (100MHz, C...

Embodiment 2

[0043] Example 2 Spectral response of BTDA-RSS to biothiols

[0044] (1) Cys test the spectral response of BTDA-RSS in PBS / DMSO (1 / 1, v / v, pH 7.4):

[0045] like Figure 4 As shown, after adding Cys, BTDA-RSS exhibited a very weak red shift, and the solution color changed from colorless to yellow. image 3 a depicts the fluorescence spectrum of Cys by BTDA-RSS at the excitation wavelength of 458 nm. BTDA-RSS itself had almost no fluorescence signal; however, after adding 20 μM Cys, a significant fluorescence enhancement was observed around 528 nm, and the fluorescence color changed from colorless to green. The fluorescence intensity of BTDA-RSS (F 528 nm ) at 0-4.5μM (F 528 nm =444343.83C Cys +7263.99,R 2 = 0.992) also showed a good linear relationship with Cys ( image 3 b), the detection limit is as low as 78.8 nM; most importantly, the emission intensity reaches saturation in only 60 s ( image 3 c), which is faster than most previous reports.

[0046] (2) Hcy, G...

Embodiment 3

[0052] Example 3 Mechanism of BTDA-RSS in response to biothiols

[0053] To explore the response mechanism of BTDA-RSS to biothiols, BTDA-RSS was combined with Cys / Hcy / GSH and Na 2 The interactions between S were carried out by mass spectrometry analysis ( Figure 7 ). with Cys / Hcy / GSH and Na 2 After the S reaction, the mass peak of free BTDA-RSS at m / z=580.0950 was no longer observed ([BTDA-RSS+H]+, calculated value of BTDA-RSS: 579.0882), while m / z=350.1322[ BTDA-RSS+Cys]+, 350.1318[BTDA-RSS+Hcy]+, 350.1321[BTDA-RSS+GSH]+ and 350.1323[BTDA-RSS+Na2S]+ correspond to the new peaks of BTDA ([BTDA+H]+, Calculated as BTDA: 349.1249). Meanwhile, other peaks at m / z=287.15 (calcd: 287.0212), 301.14 (calcd: 302.1441), 473.34 (calcd: 474.1096) and 168.02 (calcd: 168.0199) were respectively proved to be the corresponding by-products. Based on these observations, we can propose that BTDA-RSS is associated with biothiols and Na 2 The fluorescence response of S may be figure 1 The r...

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Abstract

The invention relates to a lipid droplet targeting and biological thiol-sensitive fluorescent probe for cancer cell tissue diagnosis and preparation and application thereof, the specific structural formula of the fluorescent probe is as follows: the fluorescent probe has ultrafast response time (Cys / Hcy / GSH is 60s, and Na2S is 240s) to a biological thiol fluorescence signal, meanwhile, the fluorescent probe shows remarkable LDs targeting ability, and the fluorescent probe can be applied to the diagnosis of cancer cells. The compound has been applied to biological mercaptan selective imaging in living cell LDs; more importantly, the probe can be used for distinguishing cancer cells / tissues from normal cells / tissues, and can also be used for diagnosing surgical specimens of cancer patients.

Description

technical field [0001] The invention belongs to the field of organic fluorescent probes, and in particular relates to a lipid droplet-targeted and biological thiol-sensitive fluorescent probe for cancer cell tissue diagnosis, as well as preparation and application. Background technique [0002] Cancer, a terminal illness, has become one of the most pressing public health problems. Despite the daunting statistics of new cancer cases and deaths every day, about 30% of cancer patients can be saved if diagnosed and treated early and promptly. Current genomics and proteomic-based studies have uncovered many tumor markers that have indeed greatly improved the level of diagnosis. However, due to the genetic or phenotypic heterogeneity of cancer cells, it is often impossible to diagnose a wide range of cancers using existing markers. Therefore, there is an urgent need to develop good tumor markers to effectively distinguish various cancer cells from normal cells. [0003] Lipid d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/64C09K11/06G01N21/64
CPCC07D277/64C09K11/06G01N21/6428C09K2211/1037C09K2211/1007G01N2021/6417Y02P20/55
Inventor 张跃伟王丹于雪樊丽朱守俊张宁暂琪成乐琴
Owner JILIN INST OF CHEM TECH
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