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Artificial deoxyribose responding to low-oxygen microenvironment and application of artificial deoxyribose

A nucleotide and cycloalkyl technology, applied in artificial deoxyribose and its application in cancer diagnosis and treatment, can solve the problems of unsatisfactory targeting and biological stability in low-oxygen microenvironment

Pending Publication Date: 2022-05-20
RENJI HOSPITAL AFFILIATED TO SHANGHAI JIAO TONG UNIV SCHOOL OF MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the targeting and biological stability of PET probes in the hypoxic microenvironment are still unsatisfactory

Method used

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  • Artificial deoxyribose responding to low-oxygen microenvironment and application of artificial deoxyribose
  • Artificial deoxyribose responding to low-oxygen microenvironment and application of artificial deoxyribose
  • Artificial deoxyribose responding to low-oxygen microenvironment and application of artificial deoxyribose

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0082] In the preparation method of the present invention, each reaction is usually carried out in an inert solvent at a reaction temperature of -78°C to 150°C (preferably 20 to 120°C). The reaction time of each step is usually 0.5-48 hours, preferably 2-12 hours.

[0083] Pharmaceutically acceptable salts, solvates, stereoisomers, tautomers

[0084] As used herein, the term "pharmaceutically acceptable salt" refers to the salts formed between the compounds of the present invention and pharmaceutically acceptable inorganic and organic acids, wherein preferred inorganic acids include (but are not limited to): hydrochloric acid, hydrogen Bromic acid, phosphoric acid, nitric acid, sulfuric acid; preferred organic acids include (but are not limited to): formic acid, acetic acid, propionic acid, succinic acid, naphthalene disulfonic acid (1,5), subacidic acid, oxalic acid, tartaric acid, lactic acid , salicylic acid, benzoic acid, valeric acid, diethylacetic acid, malonic acid, succ...

Embodiment 1

[0107] Example 1 Preparation of a stress-responsive deoxyribose probe based on 5-(bromomethyl)-1-methyl-2-nitro-1H-imidazole

[0108] 1.1 Preparation of compound 1 (5-(bromomethyl)-1-methyl-2-nitro-1H-imidazole)

[0109] The specific operation process is as follows:

[0110]

[0111] Under the protection of nitrogen, slowly add PPhBr 3 (19 mmol) and maintained at 0° C. for 5 hours. After the reaction was monitored by TLC, the solvent was concentrated under reduced pressure to remove the solvent, and the target compound was separated by column chromatography with high yield (yield 81%).

[0112] Compound 1: (5-(Bromomethyl)-1-methyl-2-nitro-1H-imidazole):

[0113] 1 H NMR (500MHz, CDCl 3 ), δ (ppm) = 7.21 (s, 1H), 4.50 (s, 2H), 4.07 (s, 3H); 13 C NMR (126MHz, CDCl 3 ), δ (ppm) = 152.20, 133.08, 128.35, 34.07, 18.95. MS (ESI) m / z for C 5 h 6 BrN 3 o 2 :218.9643 (calcd.), 218.9651 (expt.).

[0114] 1.2 Preparation of Compound 2

[0115]

[0116] Under nitrogen p...

Embodiment 2

[0155] Example 2 Preparation of a stress-responsive deoxyribose probe based on 2-(bromomethyl)-1-methyl-5-nitro-1H-imidazole

[0156] 2.1 Preparation of compound 10 (2-(bromomethyl)-1-methyl-5-nitro-1H-imidazole)

[0157]

[0158] Under the protection of nitrogen, slowly add PPhBr 3 (19 mmol), and maintained at 0 ° C for 30 min, then slowly rose to room temperature to continue the reaction for 5 h. After the reaction was monitored by TLC, the solvent was concentrated under reduced pressure to remove the solvent, and the target compound was obtained by column chromatography with high yield (yield 85%).

[0159] Compound 10: 2-(Bromomethyl)-1-methyl-5-nitro-1H-imidazole:

[0160] 1 H NMR (500MHz, CDCl 3 ), δ (ppm) = 7.81 (s, 1H), 4.50 (s, 2H), 3.82 (s, 3H); 13 C NMR (126MHz, CDCl 3 ), δ (ppm) = 162.08, 139.44, 136.35, 34.06, 28.85; MS (ESI) m / z for C 5 h 6 BrN 3 o 2 :218.9643 (calcd.), 218.9655 (expt.).

[0161] 2.2 Preparation of compound 11

[0162]

[0163] U...

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Abstract

The invention provides artificial deoxyribose responding to a low-oxygen microenvironment and application. Specifically, the invention provides a compound as shown in formula (I), or an optical isomer, a hydrate, a solvate or a pharmaceutically acceptable salt thereof. The compound disclosed by the invention can be used as a molecular probe for stress response to a low-oxygen microenvironment, has excellent microenvironment targeting property and biological stability, and can be used for diagnosing and treating cancers or tumors (especially solid tumors) characterized by the low-oxygen microenvironment.

Description

technical field [0001] The invention relates to the technical field of compounds and biochemistry, in particular to artificial deoxyribose in response to hypoxic microenvironment and its application in cancer diagnosis and treatment. Background technique [0002] The hypoxic microenvironment is the most significant physiological feature of malignant solid tumors, and it is also one of the determinants of the therapeutic effect of the disease. As early as the 1960s, Tomlinson and Gray discovered that hypoxia existed in human tumor tissues. Semenza, Ratcliffe and Kaelin conducted in-depth studies on this phenomenon, first explaining how cells perceive and adapt to changes in the oxygen supply environment, and found that hypoxia inducible factors (HIF) are the key proteins that control changes in oxygen in cells. [0003] At present, a large number of research results have proved that the hypoxic microenvironment not only has an important impact on tumor cell proliferation, ap...

Claims

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Application Information

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IPC IPC(8): C07H19/10C07H1/02C07H1/00A61K31/7068A61K31/713A61K31/7088A61P35/00A61K51/04
CPCC07H19/10C07H1/02C07H1/00A61P35/00A61K51/0491
Inventor 不公告发明人
Owner RENJI HOSPITAL AFFILIATED TO SHANGHAI JIAO TONG UNIV SCHOOL OF MEDICINE
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