Phloroglucinol derivative capable of inhibiting PTP1B activity, and preparation method and applications thereof

A technology of phloroglucinol and inhibitory activity, which is applied in the field of phloroglucinol derivatives that can inhibit PTP1B activity and its preparation and application, and can solve problems such as type 2 diabetes

Active Publication Date: 2017-07-04
NORTHEASTERN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The technical effect of this patented method described by researchers has been explored through experiments conducted over different types of lipophilic substances called Phlorogenins A (PPT1) and B (Phlorigenin). These chemicals were found effective against various enzyme proteases involved in blood sugar metabolism such as p-glutathione peroxidase-1 , α -amyltransferase-2, transaminases, carboxypeptide hydrolase-3, amylopexymethyl transferring factor-4, cyclooxygenase 1, catalysed reactions involving other molecules like prostaglandine synthetase, gluconeotensors, adenosynthesis factors, histone deacetylating agents, etc., which are associated with abnormalities including type 2 diarrhea caused by insulitis, hyperlipemia, liver disease, necrosis, heart failure, stroke, arteriosclerotic diseases, cancer, Parkinson' s syndrome, Alzheimer’s Disease, autistic disorders, multiple sidedness, muscle spasms, dystonia, anxiety, sleep apnea, menstrual irregularities, gastrointestinal bleeding, hypopituitaria, sexual problems due to excessive weight loss, bariatric surgery, chronic renal impairment, cardiovascular conditions, strokes, brain damage from high levels of free radical oxygen species, inflammations, autoimmune responses, gene silencing, aging processes, tumor growth, painful joint movement, rheumatoid arthritis, skin burnings, eye injuries, wounds, ulcers, asthma attacks, immunological defenses, tissue regenerative medicine treatments, and drug development efforts aimed at finding new therapies targeting these mechanisms without causing negative side effects.

Problems solved by technology

This patented technical problem addressed in this patents relates to finding novel substances able to prevent excessive activation of certain enzyme proteins called pltype II/type 2 diabtesmimetics like Insulin Phenyl Sulfotransferases-1(PST1) and Stabilizers against glucose intake into cells due to their ability to lower glycaemia without causing harmful symptoms associated therewith.

Method used

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  • Phloroglucinol derivative capable of inhibiting PTP1B activity, and preparation method and applications thereof
  • Phloroglucinol derivative capable of inhibiting PTP1B activity, and preparation method and applications thereof
  • Phloroglucinol derivative capable of inhibiting PTP1B activity, and preparation method and applications thereof

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Embodiment 1

[0036] Preparation of acylphloroglucinol derivatives with fatty side chains

[0037] 1. Preparation of black ink seed extract extract

[0038] (1) Preparation of extract

[0039] The black ink seeds (5kg) were pulverized, and the pulverized seed powder was cold-soaked for 24 hours with petroleum ether 10L, filtered, and this step was repeated 2 times. The petroleum ether extract was discarded, and the filter residue was cold-soaked in 10 L of 70% acetone-water solution for 4 times, each time for 24 hours, filtered, and the filtrates were combined to obtain the black black seed extract.

[0040] (2) Preparation of extract extract

[0041] The above extract was concentrated under reduced pressure at a temperature of ≤40°C to remove acetone and water to obtain 1200 g of crude extract.

[0042] 2. Separation and purification

[0043] (1) Disperse the above-mentioned 70% acetone-water extract in 2.5L water to make a suspension, and extract the suspension 4 times with ethyl acet...

Embodiment 2

[0080] PTP1B inhibitory activity assay

[0081] 1 Experimental principle and method

[0082] (1) The activity of PTP1B was determined based on the principle that the product of PTP1B hydrolyzing one phosphate group of p-nitrophenylphosphate (p-NPP) has absorption at a wavelength of 405 nm.

[0083] (2) 100μL reaction system: p-NPP 2mM; 1.15μg / mL GST-PTP1B1-321 protein solution; sample or DMSO; buffer [50mM 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES), pH7. 3; 100 mM NaCl; 0.1% bovine serum albumin (BSA); 1 mM dithiothreitol (DTT)].

[0084] (3) Experimental method: Add 1 μL of PTP1B protein solution (0.115 mg / mL), 1 μL of test sample or positive control sample or 1 μL of DMSO, and 96 μL of buffer solution in a 96-well plate, mix well, and incubate at 30°C for 10 minutes. Then 2 μL of p-NPP (20 mM) was added to react for 30 min, and finally 3M NAOH was added to terminate the reaction, and the absorbance was measured at 405 nm using a SpectraMax MD5 microplate re...

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PUM

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Abstract

The invention discloses a phloroglucinol derivative capable of inhibiting PTP1B activity, and a preparation method and applications thereof, and more specifically relates to a phloroglucinol compound which is obtained via extraction and separation from Eugenia jambolana Lam seeds, a preparation method thereof, and applications of the phloroglucinol compound in preparing drugs used for treating diabetes and obesity, or inhibitors of protein tyrosine phosphatase 1B (PTP1B). The general molecular formula of the phloroglucinol compound is represented by formula I, wherein R1 is used for representing methyl or hydrogen, R2 is used for representing methyl or hydrogen, R1 and R2 are used for representing the same or the different groups, and R3 is used for representing an alkane or olefin side chain containing 12 to 26 carbon atoms. The phloroglucinol compound is a novel compound with excellent PTP1B inhibition effect; the PTP1B inhibition activity IC50 value ranges from 0.42 to 3.16<mu>M; the phloroglucinol compound can be used for preparing PTP1B inhibitors, and drugs used for treating diabetes, obesity, and complications of diabetes and obesity.

Description

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Claims

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Application Information

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Owner NORTHEASTERN UNIV
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