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Near infrared fluorescence probe capable of simultaneously detecting hydrogen peroxide and peroxynitrite anoin as well as synthetic method and application thereof

A technology of peroxynitroso group and fluorescent probe is applied in the field of biological detection technology and clinical medical detection, which can solve the problem that the specific recognition of peroxidative free radicals cannot be realized, the probe lacks mitochondrial targeting functional groups, and cannot reflect quantitative changes. Regularity and other issues, to achieve the effect of being conducive to live detection, low equipment investment and production and operation costs, and improved selectivity and sensitivity

Active Publication Date: 2018-09-04
HENAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, these probes have been reported only for H 2 o 2 or ONOO - Single recognition of (Yu F, Li P, Li G, et al. Journal of the American Chemical Society, 2011, 133(29): 11030-11033; Xu K, Qiang M, Gao W, et al. Chemical Science, 2013, 4(3):1079-1086.), ignoring that the occurrence and development of tumors and other diseases are the result of the interaction of various superoxides in cells, which cannot reflect the intracellular H 2 o 2 and ONOO - Horizontal real-time and dynamic quantitative change rules, and the accuracy of repeated and step-by-step tests is low, and the system error is high
On the other hand, the existing probes lack mitochondria-targeting functional groups, have poor tissue penetration, are easily interfered by factors such as biothiols in the cytoplasm and cell membrane, and cannot achieve exclusive recognition of peroxide free radicals in mitochondria
Mitochondrial targeting function of H 2 o 2 and ONOO - Near-infrared fluorescent probes with dual recognition and simultaneous detection have not been reported yet

Method used

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  • Near infrared fluorescence probe capable of simultaneously detecting hydrogen peroxide and peroxynitrite anoin as well as synthetic method and application thereof
  • Near infrared fluorescence probe capable of simultaneously detecting hydrogen peroxide and peroxynitrite anoin as well as synthetic method and application thereof
  • Near infrared fluorescence probe capable of simultaneously detecting hydrogen peroxide and peroxynitrite anoin as well as synthetic method and application thereof

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Effect test

Embodiment 1

[0047] The synthetic method of the near-infrared fluorescent probe that simultaneously detects hydrogen peroxide and peroxynitroso anion as described above, the synthetic method comprises the steps:

[0048] Step 1, commercially available p-iodoaniline (220g, 1mol), add selenium powder (40g, 0.5mol), Cu 2 O (1.4g, 0.01mol), ethylenediamine (0.6g, 0.01mol), KOH (12g, 0.01mol), DMSO (500mL), microwave reaction at 100℃, 1h. After the reaction was completed, it was poured into 5 L of ice water, stirred, filtered, washed with a large amount of water, and dried to obtain di-p-amino-phenylselenide with a yield of 72%.

[0049] Step 2, place the two-p-aminophenylselenide prepared in step 1 in a 1500ml three-necked bottle, add 200ml water and 200ml ether, K 2 CO 3 50g. Slowly add 200ml of ether solution of 105g (0.5mol) of compound 2-chloroselenoylbenzoyl chloride dropwise under ice-cooling condition, a milky yellow precipitate is formed, then stir at -5°C for about 2h, then filter ...

Embodiment 2

[0054] The synthetic method of the near-infrared fluorescent probe that simultaneously detects hydrogen peroxide and peroxynitroso anion as described above, the synthetic method comprises the steps:

[0055] Step 1, commercially available p-iodoaniline (220g, 1mol), add selenium powder (80g, 1.05mol), Cu 2 O (7g, 0.05mol), ethylenediamine (3g, 0.05mol), KOH (30g, 0.05mol), DMSO (1000mL), reflux at 180°C for 3h. After the reaction was completed, it was poured into 10L of ice water, stirred, filtered, washed with a large amount of water, and dried to obtain di-p-amino-phenylselenide with a yield of 86%.

[0056] Step 2, place the two-p-aminophenylselenide prepared in step 1 in a 5000ml three-necked bottle, add 500ml water and 500ml ether, K 2 CO 3 500g. Slowly add 210g (1.05mol) of compound 2-chloroselenoylbenzoyl chloride in 500ml of diethyl ether solution under ice-cooling condition, a milky yellow precipitate is formed, then stir at 35°C for about 12h, then filter with suc...

Embodiment 3

[0061] The synthetic method of the near-infrared fluorescent probe that simultaneously detects hydrogen peroxide and peroxynitroso anion as described above, the synthetic method comprises the steps:

[0062] Step 1, commercially available p-iodoaniline (220g, 1mol), add selenium powder (40g, 0.5mol), Cu 2 O (7g, 0.05mol), ethylenediamine (3g, 0.05mol), KOH (30g, 0.05mol), DMSO (1000mL), microwave reaction at 120°C for 1h. After the reaction, pour into 10L of ice water, stir, filter, wash the solid with a large amount of water, and dry to obtain di-p-amino-phenylselenide with a yield of 90%.

[0063]Step 2, place the two-p-aminophenylselenide prepared in step 1 in a 3000ml three-necked bottle, add 500ml acetonitrile, K 2 CO 3 300g. Slowly add 300ml of ether solution of 165g (0.75mol) of compound 2-chloroselenoylbenzoyl chloride dropwise under ice-cooling condition, a milky yellow precipitate is formed, then stir at 15°C for about 6h, then suction filter, take the filter resi...

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Abstract

The invention relates to a near infrared fluorescence probe capable of simultaneously detecting hydrogen peroxide and peroxynitrite anoin as well as a synthetic method and application thereof. The near infrared fluorescence probe is formed by binding near infrared cyanine fluorescent dyes, a mitochondrial targeted group triphenylphosphonium salt and diselenium constitutional units by virtue of chemical covalent bonds. An excitation-emission wavelength is in a near infrared region, the detection sensitivity of the method can be improved, and the detection limit of the testing method is reduced.The near infrared fluorescence probe is expected to realize differentiated simultaneous quantitative determination of H2O2 and ONOO- in cells, and has a certain theoretical significance for dynamically observing and researching production, metabolism and mutual transformation of reactive oxide species in living mitochondria as well as process pathways and mechanisms that dynamically damage livingorganisms. Moreover, a useful tool is provided for detecting indexes in aspects of cell functions including cell activity, cytotoxicity, cell apoptosis, cell membrane potential, cell cycle and the like.

Description

technical field [0001] The invention relates to the fields of biological detection technology and clinical medical detection, in particular to a near-infrared fluorescent probe for simultaneous detection of hydrogen peroxide and peroxynitroso anions, a synthesis method and application thereof. Background technique [0002] Mitochondria are organelles wrapped in a double-membrane structure that play a vital role in the energy metabolism of cells. Studies have found that various regulation of cellular functions, including cell signaling, metabolism, autophagy, aging, and tumorigenesis, are directly related to the quality and activity of mitochondria. Excessive superoxide ion free radicals (including hydrogen peroxide and peroxynitrite anions, etc.) produced by mitochondria are the main cause of many oxidative stress diseases (such as Parkinson's disease, Alzheimer's disease, etc.). [0003] In recent years, near-infrared fluorescence bioimaging technology has attracted more a...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F9/6558G01N21/64
CPCC07F9/65583C09K11/06C09K2211/1007C09K2211/1029C09K2211/104G01N21/6486
Inventor 冯书晓杨春梅
Owner HENAN UNIV OF SCI & TECH
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