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Double-open-loop derivatives and preparation methods of cyperapuinone and analogues and application in CIK cell culture

A double ring-opening and derivative technology, which is applied in the direction of biochemical equipment and methods, cell culture active agents, and the preparation of organic compounds, can solve the problems that have not been disclosed for the proliferation of sedgequinone and the promotion of stem cell differentiation, and there is no single furan ring. , reports on ring-opening derivatives of bisfuran rings, etc.

Active Publication Date: 2018-04-06
上海美白臻生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] After searching, the prior art has not disclosed the use of sedgequinone and its analogs to promote the proliferation of CIK cells and NK cells and to promote the differentiation of stem cells, and there is no single-furan ring and difuran ring-opening derivatives of sedgequinone and its analogues. reports

Method used

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  • Double-open-loop derivatives and preparation methods of cyperapuinone and analogues and application in CIK cell culture
  • Double-open-loop derivatives and preparation methods of cyperapuinone and analogues and application in CIK cell culture
  • Double-open-loop derivatives and preparation methods of cyperapuinone and analogues and application in CIK cell culture

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Preparation of single ring-opened derivatives of sedgequinone and its analogues

[0047] First, add syringoquinone, norsyringoquinone, and hydroxysyringoquinone respectively to acidic aqueous solution (deionized water is adjusted to pH 6.3 with hydrochloric acid, of course other volatile acids such as nitric acid or formic acid can also be used instead), 4 mg of starting material was added to 1 mL of acidic aqueous solution. Then move the solution into a reaction kettle, seal it and carry out a hydrothermal reaction at a temperature of 180° C. for a reaction time of 10 hours, and naturally drop to normal temperature after the reaction is completed. Finally, heat and concentrate, freeze-dry when the pH of the solution is close to neutral to obtain the single-ring-opening derivatives of syringoquinone, the single-ring-opening derivatives of norsyringoquinone, and the single-ring-opening derivatives of hydroxysyringoquinone, all with a purity of 95 %above. See...

Embodiment 2

[0048] Example 2: Preparation of double ring-opened derivatives of sedgequinone and its analogues

[0049] First, add syringoquinone, norsyringoquinone, and hydroxysyringoquinone respectively to acidic aqueous solution (deionized water is adjusted to pH 5.4 with hydrochloric acid, of course other volatile acids such as nitric acid or formic acid can also be used instead), 4 mg of starting material was added to 1 mL of acidic aqueous solution. Then move the solution into a reaction kettle, seal it and carry out a hydrothermal reaction at a temperature of 180° C. for a reaction time of 10 hours, and naturally drop to normal temperature after the reaction is completed. Finally, heat and concentrate, and freeze-dry when the pH of the solution is near neutral to obtain syringoquinone double-ring-opening derivatives, norsyringoquinone double-ring-opening derivatives, and hydroxysyringoquinone double-ring-opening derivatives, all of which have a purity of more than 95%. See Table 1-...

Embodiment 3

[0056] Example 3: Cycloquinone and its analogues improve CIK cell cryopreservation recovery rate

[0057] 1. Experimental materials

[0058] AIM-VCTS TM The medium was purchased from Gibco, recombinant human interleukin 2 (rh IL-2) was purchased from Shuanglu Pharmaceutical; lymphocyte separation fluid was purchased from Nycomed Pharma (Nycomed PharmaAS, Oslo, Norway), and APC-labeled anti-CD56 ( CD56-APC), PE-labeled CD4 (CD4-PE), PerCP-labeled CD3 (CD3-PerCP), APC-H7-labeled CD8 (CD8-APC-H7) monoclonal antibodies were all purchased from BD Company.

[0059] 2. CIK cell isolation, culture expansion, flow detection

[0060] The peripheral blood of healthy volunteers was drawn into a centrifuge tube containing sodium heparin, and the serum and whole blood cells were obtained by centrifugation, and the whole blood cells were subjected to density gradient centrifugation to obtain mononuclear cells (PBMCs). Harvested PBMCs were resuspended in AIM-VCTS containing 10% inactivated...

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Abstract

The invention discloses double-open-loop derivatives and preparation methods of cyperapuinone and analogues and application in CIK cell culture. It is found in the invention that the cyperapuinone andits analogues demethylcyperapuinone and hydroxycyperapuinone have multiple types of pharmacological activity, for example, the cyperapuinone and its analogues can serve as cryoprotective agents for CIK and NK cells and can promote in-vitro proliferation of the CIK and NK cells and promote osteogenesis and differentiation of adipose-derived stem cells. The invention also provides single-open-loopderivatives and double-open-loop derivatives and preparation methods of the cyperapuinone and its analogues. The single-open-loop derivatives and double-open-loop derivatives of the cyperapuinone andits analogues can promote in-vitro proliferation of the CIK cells. It is found through retrieval that the application of the cyperapuinone and its analogues in promotion of CIK and NK cell proliferation and osteogenesis and differentiation of adipose-derived stem cells is not disclosed in the prior art and single-furan-ring derivatives and double-furan-ring open-ring derivatives of the cyperapuinone and its analogues is also not reported.

Description

technical field [0001] The present invention belongs to the field of chemistry and relates to the development and utilization of known natural products, in particular to the application of sedgequinone and its analogues norsyringone and hydroxysyringone in promoting the proliferation of CIK cells and NK cells and the differentiation of stem cells. It also relates to single-ring-opening derivatives and double-ring-opening derivatives of sedgequinone and its analogues, their preparation methods and their application in CIK cell culture. Background technique [0002] Cycloquinone and its analogues, norsycloquinone and hydroxysycloquinone, are three quinone compounds isolated from the whole plant of P. bifida. Their chemical structures and other information are shown below. [0003] [0004] There are very few studies on these three compounds, and the relevant activity reports are almost blank. The applicant's research found that these three compounds have excellent effects ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/38C07C46/00C07D307/80C07D307/79A61K31/122A61K31/343A61P19/08C12N5/0783
CPCC07C50/38C07D307/79C07D307/80C12N5/0638C12N5/0646C12N2501/999
Inventor 钟弦王倩付俊毅林溪
Owner 上海美白臻生物科技有限公司
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