1,3,4-oxadizaole structure unit-containing Rhodamine B pH fluorescence probe and applications thereof

Inactive Publication Date: 2013-04-03
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some reported rhodamine B-type pH probes have been used to monitor the pH value in lysosomes, these probes tend to cause "alkaline effects", that is, after long-term incubation, they will cause pH in lysosomes The value rises, affecting the monitoring results

Method used

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  • 1,3,4-oxadizaole structure unit-containing Rhodamine B pH fluorescence probe and applications thereof
  • 1,3,4-oxadizaole structure unit-containing Rhodamine B pH fluorescence probe and applications thereof
  • 1,3,4-oxadizaole structure unit-containing Rhodamine B pH fluorescence probe and applications thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of Rhodamine B pH Fluorescent Probes Containing 1,3,4-Oxadiazole Structural Units

[0033] 320 mg (0.5 mmol) of compound 1 and 80 mg (0.5 mmol) of compound 2 were dissolved in 10 mL of dry acetonitrile, 104 mg (0.75 mmol) of potassium carbonate was added, and the mixture was heated to reflux and reacted for 2 hours. After cooling, potassium carbonate was filtered off, and the filtrate was concentrated under reduced pressure to obtain a crude product. Purified by silica gel column chromatography (2:1, petroleum ether-ethyl acetate) to obtain 265 mg of light yellow compound 3, which is a rhodamine B-type pH fluorescent probe containing 1,3,4-oxadiazole structural units, the yield : 82.7%, melting point: 133-135°C.

[0034] Above-mentioned synthetic route reaction formula is as follows

[0035]

[0036] Infrared spectrum measurement: IR (KBr) ν: 3406 (N-H), 1615 (C=O) cm -1 .

[0037] H NMR spectrum determination: 1 HNMR(d 6 -DMSO,400MHz))δ(ppm):1.10(t,1...

Embodiment 2

[0040] Prepare 10 mL of the probe 3 (10 μM) solution (ethanol / Britton-Robinson buffer solution, 40 mM acetic acid, phosphoric acid, boric acid, 1:9, volume ratio, 0.1 M NaCl) under the gradient pH value (3.72-7.21), respectively. Perform UV-visible spectrophotometry and fluorescence spectrophotometry tests, and make a curve of the fluorescence intensity at 603nm as a function of the pH value.

[0041] The results showed that probe 3 had a good response to the pH value. After the pH value changed from 6.7 to 4.4, its fluorescence intensity was increased by about 46 times, which had a good fluorescence enhancement effect and could improve the sensitivity and accuracy of the signal. ( figure 2 , 3 )

Embodiment 3

[0043] After adding various metal ions to the solution of probe 3 (10 μM) with a pH value of 4.74 (ethanol / Britton-Robinson buffer solution, 40 mM acetic acid, phosphoric acid, boric acid, 1:9, volume ratio, 0.1M NaCl), Test its fluorescence intensity change. (excitation wavelength (λ ex ), 565nm; Al 3+ ,Cu 2+ , Fe 3+ ,Zn 2+ ,Cd 2+ ,Hg 2+ , Ni 2+ ,Co 2+ ,Pb 2+ , Ag + The concentration is 200μM, Na + and K + Both are 10mM, Ca 2+ and Mg 2+ Both are 5mM)

[0044] After adding various metal ions to the solution of probe 3 (10 μM) with a pH value of 7.21 (ethanol / Britton-Robinson buffer solution, 40 mM acetic acid, phosphoric acid, boric acid, 1:9, volume ratio, 0.1M NaCl), Test its fluorescence intensity change. (excitation wavelength (λ ex ), 565nm; Al 3+ ,Cu 2+ , Fe 3+ ,Zn 2+ ,Cd 2+ ,Hg 2+ , Ni 2+ ,Co 2+ ,Pb 2+ , Ag + The concentration is 200μM, Na + and K + Both are 10mM, Ca 2+ and Mg 2+ Both are 5mM)

[0045] The results show that the response o...

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Abstract

The invention discloses a 1,3,4-oxadizaole structure unit-containing Rhodamine B pH fluorescence probe, the structure of which is shown as the formula (I) in the specification. The invention further discloses applications of the probe to monitoring the change of pH values and specifically marking lysocome in living cells. The probe does not emit fluoresce under the neutral and alkaline conditions; after the pH value is smaller than 7, the fluorescence intensity is fast enhanced along with the reduction of the pH value and can achieve the maximum value when the pH value is about 4.4; the pH sensitivity of the fluorescence detection ranges from 6.7 to 4.4, and the fluorescence intensity and the pH are in linear relation from pH 4.7 to 5.7; good capability of interference resistance to various metal ions can be achieved under acidity condition; and the probe is very suitable for monitoring the pH value under the complicated interior environment of the living cells in real time, especially specifically marking lysocome and monitoring the change of pH value in the lysocome.

Description

technical field [0001] The invention relates to a rhodamine B class pH fluorescent probe containing 1,3,4-oxadiazole structural unit and its application as pH fluorescent probe in living cells. Background technique [0002] Important physiological processes in cells such as cell metabolism, signal transduction, cell growth, apoptosis, and autophagy are closely related to pH. Small changes in the pH value of cells can lead to cell dysfunction, affecting the physiological functions of the body and leading to the occurrence of various diseases, such as cancer and Alzheimer's disease. Lysosomes in cells have a slightly acidic environment (pH4.5–5.5), which contain a large number of hydrolytic enzymes and secreted proteins, which have important functions. Therefore, monitoring pH changes in living cells is essential for studying cellular functions and physiological and pathological processes. [0003] Rhodamine B has the advantages of high quantum yield, large molar extinction ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
Inventor 赵宝祥苗俊英张尚立吕洪水刘静
Owner SHANDONG UNIV
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