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Heptamethine cyanine small-molecular compound containing diphosphate structure and preparation method and application thereof

A small molecule compound, the technology of heptacyanine, which is applied in the field of small molecule compounds and preparation of heptacyanine, can solve the problem of not having bone-targeted accumulation and the like, and achieve the effect of preventing bone loss.

Pending Publication Date: 2021-11-30
ARMY MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the early stage, the applicant reported a new type of organic small molecule NIRCP-61 of Qijiachuan, and confirmed that it can significantly improve the protection of stem cells against radiation (γ irradiation, 5Gy), but the disadvantage is that the small molecule does not have a bone target accumulative properties

Method used

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  • Heptamethine cyanine small-molecular compound containing diphosphate structure and preparation method and application thereof
  • Heptamethine cyanine small-molecular compound containing diphosphate structure and preparation method and application thereof
  • Heptamethine cyanine small-molecular compound containing diphosphate structure and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The synthesis of embodiment 1 intermediate compound (IR-3Q)

[0040]

[0041] IR-783 (982.9 mg) was charged into a 25 mL round bottom reaction vial and dissolved with 12 mL of anhydrous DMF. Add 3-mercaptopropionic acid (206.7mg) under stirring, heat up to 40°C after completion, continue to stir the reaction, and monitor the reaction by thin-layer chromatography. When thin-layer chromatography showed that there was no remaining IR-783, the heating was stopped, and the mixture was naturally cooled to room temperature. The solvent in the reaction solution was distilled off under reduced pressure to obtain a dark red viscous substance, which was purified by silica gel column chromatography as a dark green solid.

[0042] IR-3Q: 1H NMR (600MHz, DMSO-d): δ8.68, 8.66, 7.59, 7.58, 7.42, 7.41, 7.40, 7.40, 7.39, 7.38, 7.37, 7.37, 7.25, 7.25, 7.24, 7.23, 7.22, 7.22, 6.31, 6.29,5.73,4.16,4.15,4.14,3.35,3.34,3.33,3.31,3.05,3.03,3.02,3.01,2.97,2.95,2.94,2.86,2.70,2.63,2.62,2.6...

Embodiment 2

[0044] The synthesis of embodiment 2 target compound IR-ALN

[0045]

[0046] The above-prepared compound IR-3Q (150 mg) was added to a 25 mL reaction bottle, and 8 mL of dichloromethane was added. After stirring and dissolving, the condensing agent dicyclohexylcarbodiimide (DCC, 340.4 mg) and the activator N-hydroxysuccinimide (NHS, 190 mg) were added. After the addition was complete, the stirring reaction was continued at 20° C. for 12 h, and a large amount of white solid was formed. After suction filtration under reduced pressure, the filtrate was concentrated under reduced pressure to obtain the carboxyl-activated intermediate compound IR-3Q, which was carried out to the next step without further purification.

[0047] Sodium alendronate (26 mg) was dissolved in 4 mL of boric acid buffer (pH=8.4) to obtain solution a. At the same time, the intermediate IR-3Q prepared above was redissolved with anhydrous acetonitrile (2 mL) to obtain solution b. Under stirring at room...

Embodiment 3

[0049] Optical performance test of embodiment 3 IR-ALN

[0050] Dissolve IR-ALN in DMSO, prepare a stock solution with a concentration of 10 mM, and store it at -20°C until use; before use, dilute with phosphate buffer (PBS, pH 7.22) to obtain a final concentration of 2 μM IR-ALN working fluid. Utilize ultraviolet-visible-near-infrared spectrometer (purple UV-3600 scanning spectrophotometer, Japan Shimadzu) to test this solution and obtain its absorption spectrum; Fluorescence spectra in the wavelength range of 750-900nm (such as image 3 shown).

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Abstract

The invention relates to a heptamethine cyanine small-molecular compound containing a diphosphate structure and a preparation method and application thereof. According to the invention, a diphosphate structure with a bone targeting characteristic is introduced into a conjugated parent structure of a heptamethine cyanine small molecule, and the heptamethine cyanine small-molecular compound with high-selectivity recognition of bone tissues and near-infrared fluorescence imaging is constructed. The heptamethine cyanine compound has a good prevention and treatment function on radiation-induced bone loss, and has potential significance in prevention of radiation damage. The compound has the advantages of simple preparation method and low cost.

Description

technical field [0001] The present invention relates to a heptacyanine compound, in particular to a heptacyanine small molecule compound, a preparation method and an application thereof. Background technique [0002] With the development of nuclear energy and nuclear technology applications, the potential risk of people suffering from radiation damage has greatly increased, including nuclear radiation accidents, space exploration, cancer treatment, radiological diagnosis and radiation processing and other fields. Related studies have shown that the clinical symptoms of radiation damage to the body are hematopoietic dysfunction, and bone marrow damage is more common in radiation damage. As the main source of hematopoietic stem cells in the human body, bone marrow is located in the medullary cavity of long bones and all cancellous bone, and is the most sensitive organ to the cytotoxic response of ionizing radiation; in addition, radiation can reduce the proliferation and diffe...

Claims

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Application Information

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IPC IPC(8): C07F9/572C09K11/06A61K31/675A61P39/00A61P19/08A61K49/00
CPCC07F9/5728C09K11/06A61P39/00A61P19/08A61K49/0032C09K2211/1029Y02P20/55
Inventor 史春梦隆磊王钰吴峰谭旭
Owner ARMY MEDICAL UNIV
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