CN113527151A - Action mechanism and application of anti-tumor small molecular compound - Google Patents
Action mechanism and application of anti-tumor small molecular compound Download PDFInfo
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- CN113527151A CN113527151A CN202010314334.1A CN202010314334A CN113527151A CN 113527151 A CN113527151 A CN 113527151A CN 202010314334 A CN202010314334 A CN 202010314334A CN 113527151 A CN113527151 A CN 113527151A
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- 229940041181 antineoplastic drug Drugs 0.000 claims abstract description 10
- 201000002743 tongue squamous cell carcinoma Diseases 0.000 claims abstract description 10
- -1 small molecule compound Chemical class 0.000 claims description 27
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- IUZGUIPYVGPQFT-UHFFFAOYSA-N N-[4-(naphthalen-2-ylmethyl)phenyl]ethenesulfonamide Chemical compound C(=C)S(=O)(=O)NC1=CC=C(C=C1)CC1=CC2=CC=CC=C2C=C1 IUZGUIPYVGPQFT-UHFFFAOYSA-N 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
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- 230000002222 downregulating effect Effects 0.000 claims description 2
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- JUJBNYBVVQSIOU-UHFFFAOYSA-M sodium;4-[2-(4-iodophenyl)-3-(4-nitrophenyl)tetrazol-2-ium-5-yl]benzene-1,3-disulfonate Chemical compound [Na+].C1=CC([N+](=O)[O-])=CC=C1N1[N+](C=2C=CC(I)=CC=2)=NC(C=2C(=CC(=CC=2)S([O-])(=O)=O)S([O-])(=O)=O)=N1 JUJBNYBVVQSIOU-UHFFFAOYSA-M 0.000 description 2
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- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/11—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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Abstract
The invention provides a function and a possible molecular mechanism of an anti-tumor small molecular compound, wherein the compound is N- (4- (naphthalene-2-ylmethyl) phenyl) ethylene sulfonamide, and the molecular formula is C18H25N3O4The molecular structural formula is:the possible molecular mechanism of the small molecular compound is that the protein expression of an important transcription factor TEAD2 molecule in tongue squamous cell carcinoma is obviously reduced, so that the abnormal increase of tumor cells is inhibited, the apoptosis of the tumor cells is promoted, and the tumor invasion and metastasis capacity is inhibited. By molecular targeted therapyThe treatment effect is improved, and the toxic and side effects brought by broad-spectrum chemotherapy medicaments are reduced. The compound has a simple structure, is easy to synthesize, lays a good foundation for the development of new antitumor drugs, particularly innovative targeted drugs for tongue squamous cell carcinoma, and provides a wider application prospect for later-stage single-drug therapy and combined therapy.
Description
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to an action mechanism and application of an anti-tumor small molecular compound.
Background
Malignant tumors are one of the diseases that seriously endanger human health. Tongue Squamous Cell Carcinoma (OTSCC) is one of the most common malignant tumors of Oral cavity, jaw and face, and seriously threatens the life and health of patients due to its biological characteristics such as high probability of lymph node metastasis and strong invasiveness. The traditional treatment method has certain influence on the long-term prognosis and the quality of life of patients, and the 5-year survival rate is low. In addition, the various molecular mechanisms involved in the disease have not been fully elucidated. Therefore, identification of effective biomarkers is crucial to improve the diagnosis, treatment and prognostic evaluation prevention of OTSCC.
The TEADs family has been shown to be an important class of transcription factors, which are widely involved in the development of malignant tumors. Since the first discovery, TEADs were found to be evolutionarily conserved and play an important role in development, tissue homeostasis, and tumorigenesis by regulating cell growth, proliferation, differentiation, and survival. Previous studies showed that the TEAD2 molecule was more highly expressed in OTSCC samples than in paracancerous samples. Meanwhile, the abnormally expressed TEAD2 is involved in the abnormal proliferation, invasion and metastasis and other biological phenotypes of tongue squamous cell carcinoma. The highly expressed TEAD2 may also affect the prognosis of tongue squamous carcinoma to some extent. Therefore, the molecule is expected to become a new target for treating tongue squamous cell carcinoma.
Throughout the research of antitumor drugs, molecular targeted therapy has gradually replaced broad-spectrum chemotherapeutic drugs and gradually moved to the market. The research and development of novel antitumor drugs according to the strategy have great significance for the development of malignant tumor treatment technology.
Disclosure of Invention
The invention aims to provide an action mechanism and application of an anti-tumor small molecule compound, wherein the compound can show good anti-tumor activity by down-regulating the expression of a transcription factor TEAD 2.
In order to achieve the purpose, the invention adopts the technical scheme that:
an anti-tumor small molecular compound, which is characterized in that the compound is N- (4- (naphthalene)-2-ylmethyl) phenyl) ethenesulfonamide having the formula C19H18NOS, molecular structural formula:
the anti-tumor small molecular compound is applied to preparing anti-tumor drugs.
The tumor is tongue squamous cell carcinoma.
The application is characterized in that the small molecule compound can specifically down regulate the expression level of the transcription factor TEAD 2.
The application is characterized in that the small molecular compound is a drug capable of inhibiting proliferation of tongue squamous carcinoma cells.
The application is characterized in that the small molecular compound is a drug capable of promoting tongue squamous cell carcinoma apoptosis.
The application is characterized in that the small molecular compound can inhibit the migration and the movement ability of tongue squamous carcinoma cells.
The anti-tumor drug is a drug prepared from N- (4- (naphthalene-2-ylmethyl) phenyl) ethenesulfonamide and one or more pharmaceutically acceptable auxiliary materials and/or pharmaceutical excipients.
The dosage forms of the antitumor drug comprise liquid preparations, tablets, medicinal granules, soft capsules, sustained-release agents, dropping pills and injections, and the administration forms comprise oral administration and injection administration.
Compared with the prior art, the invention has the beneficial effects that:
the invention provides an anti-tumor small molecule compound, N- (4- (naphthalene-2-ylmethyl) phenyl) vinylsulfonamide, which has good targeting property and good anti-tumor activity, can be used for preparing anti-tumor medicaments, and has good clinical application prospect.
Furthermore, experimental verification proves that the small molecule compound provided by the invention can reduce the expression level of the transcription factor TEAD2 protein, and has good targeting property. The TEAD2 is used as a target point to prevent and treat the oral squamous cell carcinoma, and a new strategy is provided for treating the oral squamous cell carcinoma.
Furthermore, experimental verification proves that the anti-tumor small molecule compound N- (4- (naphthalene-2-ylmethyl) phenyl) vinylsulfonamide provided by the invention has good anti-tumor activity, and has the effects of inhibiting abnormal proliferation, promoting apoptosis and inhibiting migration and metastasis of different squamous cancer cell lines, particularly oral tongue squamous cancer cell lines. Lays a good foundation and optimistic application prospect for the development of new anti-tumor drugs and brings good news for the majority of tumor patients.
Furthermore, the antitumor small molecule compound provided by the invention can be prepared into a medicament with any one or more pharmaceutically acceptable auxiliary materials and/or pharmaceutical excipients, the preparation can be any pharmaceutically acceptable dosage form, including but not limited to liquid preparations, tablets, granules, soft capsules, sustained release agents, dropping pills or injections, and the administration forms mainly include oral administration and injection administration.
Drawings
FIG. 1 is a molecular structural formula of an anti-tumor small molecule compound.
FIG. 2 shows the expression of TEAD2 protein level in Cal-27 cells at different drug concentrations.
FIG. 3 shows the effect of small molecule compounds on the proliferation ability of tumor cells under different drug concentrations detected by the WST-1 method.
FIG. 4 is a graph showing the effect of a small molecule compound on the apoptosis ability of tumor cells detected by a flow cytometry ANNEXIN-V/PI method, wherein the upper group is a schematic apoptosis flow chart; the lower panel is a statistical result chart.
Fig. 5 is the results of invasion assay to evaluate the effect of small molecule compounds on tumor invasion and motility. Wherein the upper group is a schematic representation of cell invasion; the lower panel is a statistical result chart.
Detailed Description
The present invention is described in further detail below.
The anti-tumor small molecular compound provided by the invention is N- (4- (naphthalene-2-ylmethyl) phenyl) vinylsulfonamide, and the molecule thereofFormula is C19H18NOS, molecular structural formula is shown in FIG. 1.
The anti-tumor effect of the anti-tumor small molecule compound provided by the invention is described in detail by specific experiments and the accompanying drawings.
1. Small molecule compounds down-regulate expression of TEAD2
Western blot is used for detecting the expression condition of the small molecular compound to TEAD2 molecular level in a tongue squamous carcinoma cell line Cal-27. As shown in fig. 2, the experimental results indicate that small molecule compounds can significantly down-regulate the protein expression level of TEAD2 in Cal-27 cells, and that this down-regulation is concentration-dependent. I.e., the higher the concentration of small molecule compound, the more pronounced the downregulation of TEAD 2. The test result indicates that the small molecular compound can remarkably reduce the expression of TEAD2, and is expected to become a candidate target compound of the target.
2. Small molecule compound for inhibiting proliferation capacity of Cal-27 cell
In order to detect whether the small molecular compound has influence on the proliferation activity of CAL-27 cells, the WST-1 kit is used for detection. As shown in FIG. 3, compared with the control group, the cell proliferation ability of the drug-intervention group was significantly inhibited, the cell survival rate was gradually decreased, and the concentration gradient dependence was exhibited (P < 0.05). Under the same culture time and treatment conditions, after 48 hours, the cell survival rate of the control group is still nearly 100%, while the cell survival rate of the highest concentration drug group is less than 5%, and the tumor inhibition effect is very obvious.
3. Small molecule compound for promoting CAL-27 cell apoptosis
A flow cytometer Annexin V-PI double staining test is applied to compare whether the small molecular compound can induce the tumor cells to generate apoptosis, as shown in figure 4. Considering that the solvent DMSO of small molecule compound also has some influence on the apoptosis of tumor cells, we introduced blank control group and solvent control group (DMSO) in this experiment. The results show that compared with the blank control group, the proportion of the apoptotic cells of the solvent control group is not obviously increased, no statistical difference exists between the two groups, while the proportion of the apoptotic cells of the drug intervention group is obviously increased, and the statistical difference exists between the apoptotic cells of the drug intervention group and the control group (P is less than 0.05). The compound is suggested to be capable of effectively inducing CAL-27 cells to generate apoptosis and eliminating the influence of a solvent DMSO on the apoptosis.
4. Micromolecular compound for inhibiting tongue squamous carcinoma invasion and metastasis
Tongue squamous carcinoma cells are easy to invade and transfer, can accelerate the progress of diseases, and seriously affect the prognosis. We evaluated the effect of this small molecule compound on the ability of cell invasion by the transwell cell invasion assay. Considering that the solvent DMSO of small molecule compound also has an effect on tumor invasion, blank control and solvent control (DMSO) were also introduced in this experiment. As shown in fig. 5, we found that the cell invasion ability of the solvent control group was not inhibited and was not significantly different from that of the blank control group, compared with that of the blank control group. After the drug is dried, the number of cells passing through the chamber is obviously reduced in each visual field, and the invasion and metastasis capacity of the cells is obviously inhibited. At a drug concentration of 10. mu.M, the invasive potential of tumor cells decreased by about 50%.
The data show that the possible action mechanism of the small molecular compound is that the expression level of a transcription factor TEAD2 which is important in the occurrence and development process of tongue squamous cell carcinoma is obviously reduced, so that the proliferation of tumor cells is further inhibited, the apoptosis of the tumor cells is promoted, and the invasion and metastasis capacity of the tumor cells is inhibited, thereby effectively controlling the tumor progression.
Claims (9)
2. the use of the anti-tumor small molecule compound of claim 1 in the preparation of anti-tumor drugs.
3. The tumor of claim 2, which is squamous cell carcinoma of the tongue.
4. The use of claim 2, wherein said small molecule compound is capable of specifically down-regulating the expression level of the transcription factor TEAD 2.
5. The use according to claim 2, wherein the small molecule compound is a drug capable of inhibiting proliferation of a tongue squamous carcinoma cell.
6. The use of claim 2, wherein the small molecule compound is a drug that promotes apoptosis in squamous cell carcinoma of the tongue.
7. The use according to claim 2, wherein the small molecule compound is capable of inhibiting migration and motility of squamous cell carcinoma cells.
8. The use according to any one of claims 4 to 7, wherein the antineoplastic drug is a drug prepared from N- (4- (naphthalene-2-ylmethyl) phenyl) ethenesulfonamide and one or more pharmaceutically acceptable excipients and/or pharmaceutical excipients.
9. The use of claim 8, wherein the dosage forms of the antitumor drugs include liquid preparations, tablets, granules, soft capsules, sustained-release preparations, dripping pills and injections, and the administration forms include oral administration and injection administration.
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Citations (1)
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CN112010789A (en) * | 2019-05-31 | 2020-12-01 | 中国科学院上海药物研究所 | Vinyl sulfonamide or vinyl amide compounds, and preparation method and application thereof |
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CN112010789A (en) * | 2019-05-31 | 2020-12-01 | 中国科学院上海药物研究所 | Vinyl sulfonamide or vinyl amide compounds, and preparation method and application thereof |
Non-Patent Citations (2)
Title |
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WENCHAO LU ET AL.: "Discovery and biological evaluation of vinylsulfonamide derivatives as highly potent, covalent TEAD autopalmitoylation inhibitors", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 184, 9 October 2019 (2019-10-09), pages 111767, XP085911111, DOI: 10.1016/j.ejmech.2019.111767 * |
ZHONGWU LI ET AL.: "The Hippo transducer TAZ promotes epithelial to mesenchymal transition and cancer stem cell maintenance in oral cancer", MOLECULAR ONCOLOGY, vol. 9, 9 February 2015 (2015-02-09), pages 1091 - 1105, XP029172008, DOI: 10.1016/j.molonc.2015.01.007 * |
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