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WO2019078645A1 - Composition pharmaceutique pour un traitement anti-cancereux et procédé de préparation associé - Google Patents

Composition pharmaceutique pour un traitement anti-cancereux et procédé de préparation associé Download PDF

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Publication number
WO2019078645A1
WO2019078645A1 PCT/KR2018/012350 KR2018012350W WO2019078645A1 WO 2019078645 A1 WO2019078645 A1 WO 2019078645A1 KR 2018012350 W KR2018012350 W KR 2018012350W WO 2019078645 A1 WO2019078645 A1 WO 2019078645A1
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WO
WIPO (PCT)
Prior art keywords
cancer
cells
hydroxy
octyl
present
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Ceased
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PCT/KR2018/012350
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English (en)
Korean (ko)
Inventor
김기광
천성혜
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Industry and Academy Cooperation In Chungnam National University
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Industry and Academy Cooperation In Chungnam National University
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Priority claimed from KR1020180124248A external-priority patent/KR102142880B1/ko
Publication of WO2019078645A1 publication Critical patent/WO2019078645A1/fr
Anticipated expiration legal-status Critical
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    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form

Definitions

  • the present invention relates to a method of treating cancer in a mammal, compositions useful for such treatment, and medicaments comprising the same. More particularly, the present invention relates to a composition for chemotherapy comprising an alkyl 4-hydroxy-3,5-dialkoxybenzoate derivative or a pharmaceutically acceptable salt thereof, And pharmaceutical compositions comprising such compositions.
  • apoptosis a mechanism of apoptosis (apoptosis), a form of necrosis and self - destruction, which is a cell accident caused by cell damage.
  • apoptosis is involved in the proper regulation of cell number and plays an essential role in embryonic development and various illnesses such as degenerative neurological diseases, cardiovascular diseases and cancer.
  • cancer is caused by abnormalities in the regulation of normal processes that control cell division, differentiation, and apoptotic cell death. Since cancer cells, unlike normal cells, do not have proper self-apoptotic function, it is possible to inhibit the proliferation of cancer cells by inducing self-destructive function.
  • induction of apoptosis in cancer cells may have a positive effect on the mutual reaction between the cancer cells and the patient, in particular, the immune response as well as the direct reduction of cancer cells.
  • the present invention provides a composition for chemotherapy comprising an alkyl 4-hydroxy-3,5-dialkoxybenzoate derivative compound or a pharmaceutically acceptable salt thereof , Preferably an alkyl 4-hydroxy-3,5-dimethoxybenzoate, more preferably an octyl 4-hydroxy-3,5-dimethoxybenzoate compound Or a pharmaceutically acceptable salt thereof.
  • the present invention also provides a composition for chemotherapeutic treatment, which comprises the compound at a concentration of 60 ⁇ M or more and 120 ⁇ M or less.
  • composition of the present invention is administered intraperitoneally.
  • the present invention also provides a medicament for chemotherapy comprising the above composition for chemotherapy.
  • the present invention also provides a method of chemotherapeutic treatment using the composition for chemotherapy.
  • the anticancer therapy of the present invention is particularly directed to breast cancer, stomach cancer, cervical cancer, liver cancer, and colon cancer.
  • the present invention has the effect of reducing cell viability by specifically inducing cell cycle destruction and cell death of cancer cells without affecting cell viability of normal cells.
  • FIG. 1 shows the structures of four kinds of octyl benzoate derivative compounds (Compound A, B, C and D), wherein a compound referred to as Compound D is octyl 4- Corresponds to hydroxy-3,5-dimethoxybenzoate (Octyl 4-hydroxy-3,5-dimethoxybenzoate).
  • FIG. 2 shows the results obtained when compounds A, B, C, and D were administered at various concentrations (0, 15, and 10 mM) to breast cancer cells (MCF7 cell, MDA-MB-231 cell, SK- 30, 60, 90, and 120 [mu] M) for 24 hours. Cell viability was measured by MTS assay.
  • Figure 3 shows the effect of Compound D (octyl 4-hydroxy-3,5-dimethoxybenzoate) on MCF7 cells ( Figure 3A) and MCF 10A cells ( Figure 3B) at various concentrations (0, 60, ) For 12 hours and then measured by flow cytometry to determine the effect on the cell cycle.
  • Compound D octyl 4-hydroxy-3,5-dimethoxybenzoate
  • Figure 4 is a representative plot showing annexin V-5-fluorescein isothiocyanate (FITC) / propidium iodine (PI) staining of MCF7 cell and MCF 10A.
  • FITC annexin V-5-fluorescein isothiocyanate
  • PI propidium iodine staining of MCF7 cell and MCF 10A.
  • MCF7 cells treated with octyl 4-hydroxy-3,5-dimethoxybenzoate at a concentration of 60 ⁇ M (B in FIG. 4 and C in FIG. 4) and 120 ⁇ M (D in FIG. 4 and E in FIG. 4) is a flow cytometric analysis that measures apoptosis / necrosis using annexin V-FITC / PI staining.
  • Q1 is annexin V-FITC- / PI +
  • Q2 is annexin V-FITC + / PI +
  • Q3 is annexin V-FITC- / PI-
  • Q4 is annexin V-FITC + / PI-.
  • FIG. 5A shows the cell viability of CT26 cells treated with various concentrations (0, 15, 30, 60, 90, 120 ⁇ M) of octyl 4-hydroxy-3,5-dimethoxybenzoate.
  • 5, B, C, and D show that BALB / c mice were subcutaneously injected with CT26 cells and treated with octyl 4-hydroxy-3,5-dimethoxybenzoate every 3 days when the tumor size reached 100 mm 3
  • FIG. 5B is a photograph showing a comparison of the tumor size change in the case of not treating (Control) with that of octyl 4-hydroxy-3,5-dimethoxybenzoate (IP injection)
  • FIG. 5C shows changes in the weight of rats according to whether or not octyl 4-hydroxy-3,5-dimethoxybenzoate was injected at intervals of 3 days
  • FIG. 5D shows changes in the weight of octyl 4-hydroxy- And the change in tumor size according to the injection of 3,5-dimethoxybenzoate.
  • 6 is a graph showing changes in the concentration of octyl-4-hydroxy-3,5-dimethoxybenzoate at various concentrations (0, 1, 2, 30, 60, 90, and 120 [mu] M) for 24 hours. Cell viability was measured by MTS assay.
  • the inventors of the present invention experimented with four types of Octyl benzoate derivative compounds (Compound 1, Compound A, B, C, and D) with different functional groups substituted on the benzene ring, The present inventors have found that octyl 4-hydroxy-3,5-dimethoxybenzoate is excellent in anticancer effect and completed the present invention.
  • the present invention relates to a composition for chemotherapy for inducing cell death of cancer cells.
  • the present invention relates to an anticancer therapy comprising 4-hydroxy-3,5-dialkoxybenzoate derivative represented by the following formula (1) or a pharmaceutically acceptable salt thereof: ≪ / RTI >
  • R One -CH 3 , -CH 2 CH 3 Or - (CH 2 ) 2 CH 3 , R 2 -CH 3 , -CH 2 CH 3 Or - (CH 2 ) 2 CH 3 And R 3 - (CH 2 ) n CH 3 And n is from 6 to 10.
  • R 1 is CH 3 and R 2 is CH 3 .
  • the present invention includes an octyl 4-hydroxy-3,5-dimethoxybenzoate compound represented by the following formula (2) or a pharmaceutically acceptable salt thereof: Or a pharmaceutically acceptable salt thereof.
  • the pharmaceutical composition of the present invention can be used for the treatment or prevention of cancer.
  • Cancers that can be treated or prevented by the pharmaceutical composition of the present invention include breast cancer, colon cancer, colon cancer, rectal cancer, pancreatic cancer, gastric cancer, lung cancer, liver cancer, bladder cancer, cervical cancer, head and neck cancer, ovarian cancer, thyroid cancer, But is not limited thereto.
  • the composition of the present invention is effective for treatment and prevention of breast cancer.
  • the composition of the present invention also has a therapeutic / preventive effect on gastric cancer, cervical cancer, liver cancer and colon cancer .
  • composition refers to a therapeutically effective amount of an alkyl 4-hydroxy-3,5-dialkoxybenzoate derivative, preferably alkyl 4- Hydroxy-3,5-dialkoxybenzoate derivatives, more preferably octyl 4-hydroxy-3,5-dimethoxybenzoate (Octyl 4-hydroxy- , 5-dimethoxybenzoate) or a pharmaceutically acceptable salt thereof.
  • the pharmaceutical composition of the present invention may be selected from the group consisting of carriers, excipients, disintegrants, sweeteners, coating agents, swelling agents, lubricants, lubricants, flavors, antioxidants, buffers, bacteriostats, diluents, dispersants, surfactants, Or < / RTI >
  • a compound that exhibits activity in a pharmaceutical composition can generally be mixed with a carrier, or diluted by a carrier, or enclosed within a carrier that can be in the form of an ampoule, capsule, sachet, paper or other container have.
  • a carrier or the carrier is used as a diluent, it may be a solid, semi-solid or liquid substance, which may serve as a vehicle, excipient or medium for the present compounds.
  • the present compounds may be adsorbed to a particulate solid carrier, for example, contained in a body.
  • suitable carriers are water, salt solutions, alcohols, polyethylene glycols, polyhydroxyethoxylated castor oil, peanut oil, olive oil, gelatin, lactose, terra alba, sucrose, dextrin, magnesium carbonate Lower alkyl ethers of cellulose, silicic acid, fatty acids, fatty acid amines, fatty acids such as sucrose, cyclodextrin, amylose, magnesium stearate, talc, gelatin, agar, pectin, acacia, stearic acid or cellulose Monoglycerides and diglycerides, pentaerythritol fatty acid esters, polyoxyethylene, hydroxymethylcellulose and polyvinylpyrrolidone.
  • the carrier or diluent may include any sustained release material known in the art, such as glyceryl monostearate or glyceryl distearate, alone or mixed with wax.
  • the pharmaceutical composition according to the present invention may be formulated in the form of powders, granules, tablets, capsules, suspensions, emulsions, syrups, aerosols and the like, oral preparations, suppositories and sterilized injection solutions according to a conventional method .
  • Formulations may be mixed with adjuvants which do not react naturally with the compounds exhibiting activity.
  • adjuvants may include wetting agents, emulsifying and suspending agents, salts for influencing osmotic pressure, buffering agents and / or coloring matter preservatives, sweetening or flavoring agents.
  • salt includes organic compounds such as carboxylic acids, sulfonic acids, or amines in ionic form combined with counter ions.
  • the acid in the anionic form may be a cation such as a metallic cation such as, for example, sodium, potassium, and the like, a metallic cation;
  • Can form salts with NH 4 + and ammonium salts such as the cations of various amines, and include tetraalkylammonium such as tetramethylammonium, or cations such as trimethylsulfonium, and the like.
  • a “pharmaceutically acceptable,””pharmaceuticallyacceptable,” or “pharmacologically acceptable,” pharmacologically acceptable salt is a salt formed from an edible, It is non-toxic, such as a salt or sodium salt.
  • a “ zwitterion " is an intramolecular salt that can be in the form of a molecule having at least two ionizable groups that form anions and other cations, each providing a balance. For example, amino acids such as glycine can be present in the form of positive ions. &Quot; Positive ions " are salts within the meaning of this specification.
  • the compounds of the present invention may take the form of a salt.
  • salt means a free base or a free acid addition salt of a compound of the invention.
  • the salt may be a " pharmaceutically acceptable salt ".&Quot; Pharmaceutically acceptable salt " refers to a salt having a toxicity profile within a range that is useful in the pharmaceutical arts.
  • Suitable pharmaceutically acceptable acid addition salts may be prepared from organic or inorganic acids.
  • treatment means: (1) relieving one or more of the biological signs of the condition, (2) (a) at least one point in the biological cascade causing or causing the condition, or (b) alleviating one or more biological signs of the condition, (3) alleviating one or more symptoms, effects or side effects associated with the condition or its treatment, or (4) delaying the progress of one or more biological symptoms of the condition or condition. .
  • administration may be administered via the oral, intradermal, subcutaneous, have.
  • the pharmaceutical composition of the present invention effectively inhibits the growth of cancer cells and thus can be used for the treatment of cancer patients such as breast cancer, colon cancer, colon cancer, rectal cancer, pancreatic cancer, stomach cancer, liver cancer, bladder cancer, cervical cancer, head and neck cancer, lung cancer, ovarian cancer and prostate cancer
  • cancer patients such as breast cancer, colon cancer, colon cancer, rectal cancer, pancreatic cancer, stomach cancer, liver cancer, bladder cancer, cervical cancer, head and neck cancer, lung cancer, ovarian cancer and prostate cancer
  • the appropriate dosage may vary depending on factors such as the formulation method, the manner of administration, the patient's age, body weight, sex, pathological condition, food, time of administration, route of administration, excretion rate and responsiveness It can be prescribed.
  • the pharmaceutical composition of the present invention is characterized by containing octyl 4-hydroxy-3,5-dimethoxybenzoate in a total composition at a concentration of 60 ⁇ M to 150 ⁇ M, It is understood that the concentration is preferably 60 [mu] M to 120 [mu] M or 90 [mu] M to 150 [mu] M, more preferably 90 [mu] M to 120 [
  • individual refers to all animals, including humans, who have developed or may have developed cancer. As a specific example, it may be a mammal including a human.
  • MCF 10A cells are maintained in Dulbecco's Modified Eagle Medium.
  • Dulbecco's Modified Eagle Medium contains 10% heat-inactivated horse serum (Gibco), 100 U / ml penicillin and 100 ⁇ g / ml streptomycin (Hyclone), 10 ⁇ g / ml insulin, 100 ng / ml 12 medium (DMEM / F12, WELGENE) using cholera toxin, 0.5 ⁇ g / ml hydrocortisone and 20 ng / ml recombinant human epidermal growth factor, to be.
  • All these cells are maintained in a humidified incubator at 37 ° C, 5% CO 2 .
  • tumor volume [mm 3 ] (length [mm]) ⁇ (width [mm]) 2 ⁇ 0.5.
  • tumor volume [mm 3 ] (length [mm]) ⁇ (width [mm]) 2 ⁇ 0.5.
  • Cell viability is measured using the MTS assay. After seeding 10,000 cells per well in a 96-well plate, the next day, cells treated with various amounts of compounds or untreated are cultured for 24 hours.
  • the concentration that reduces the cell viability of cancer cells without affecting normal cells corresponds to 60 ⁇ M to 150 ⁇ M, preferably 60 ⁇ M to 120 ⁇ M or 90 ⁇ M to 150 ⁇ M, more preferably 90 ⁇ M to 120 ⁇ M (See FIG. 2).
  • Octyl 4-hydroxy-3,5-dimethoxybenzoate which is Compound D
  • AGS human caucasian gastric adenocarcinoma
  • HeLa cervical cancer Cells were treated with human cervix adenocarcinoma
  • HepG2 human hepatocellular carcinoma
  • HT29 human colorectal adenocarcinoma
  • octyl 4-hydroxy-3,5-dimethoxybenzoate has the effect of reducing the cell viability of gastric cancer, cervical cancer, liver cancer and colon cancer cells at a concentration of 60 ⁇ M to 120 ⁇ M, preferably 90 ⁇ M to 120 ⁇ M (See FIG. 6).
  • the cells After the cells reach 60-80% confluence, treat the compounds at various concentrations. After 24 hours, the cells are harvested, washed twice with cold PBS, and fixed with 70% ethanol at 4 ° C for 1 hour. Immobilized cells are washed with PBS, resuspended with propidium iodide (PI) solution (Sigma, P4170) containing RNase, and incubated for 30 minutes in dark room at room temperature. The amount of DNA is analyzed by flow cytometry.
  • PI propidium iodide
  • FIG. 3 shows the effect of the addition of octyl 4-hydroxy-3,5-dimethoxybenzoate to MCF7 cell (FIG. 3A) and MCF 10A cell (FIG. 120 ⁇ M) for 12 hours and then measured by flow cytometry to determine the effects on the cell cycle.
  • octyl 4-hydroxy-3,5-dimethoxybenzoate induces apoptosis by dysfunctioning cell cycle of MCF7 cell.
  • MCF 10A cells induce G1 arrest but do not affect cell death.
  • the cells were treated with 60, 120 ⁇ M of octyl 4-hydroxy-3,5-dimethoxybenzoate and cultured for 4 and 12 hours .
  • Cell death was observed using the FITC Annexin V Apoptosis Detection kit (BD Biosciences). Following the manufacturer's protocol, suspend the pellet with trypsin, wash twice with cold PBS, and resuspend in 100 ⁇ l buffer to a cell concentration of 1 ⁇ 10 6 cells / ml. The cells are incubated for 15 minutes in 5 ⁇ l of FITC Annexin V and 5 ⁇ l of PI at room temperature in dark space, and 400 ⁇ l buffer is added after staining. Fluorescence intensity is detected by flow cytometer.
  • FIG. 4 shows the results of measuring the apoptosis / necrosis of MCF7 cells treated with octyl 4-hydroxy-3,5-dimethoxybenzoate using annexin V-FITC / PI staining It is flow cytometric analysis.
  • Q1 annexin V-FITC- / PI +
  • Q2 is annexin V-FITC + / PI + V-FITC + / PI-
  • the ratio of Q1, Q2, Q3 and Q4 shows that octyl 4-hydroxy-3,5-dimethoxybenzoate causes cell death of MCF7 cells associated with necrosis.
  • the prepared animal model was treated with octyl 4-hydroxy-3,5-dimethoxybenzoate to compare the tumor size with the untreated control (Control).
  • FIG. 5A shows the cell viability of CT26 cells treated with various concentrations (0, 15, 30, 60, 90, 120 ⁇ M) of octyl 4-hydroxy-3,5-dimethoxybenzoate.
  • octyl 4-hydroxy-3,5-dimethoxybenzoate decreases cell viability of CT26 (see A in FIG. 5).
  • FIG. 5B, FIG. 5C, and FIG. 5D show that BALB / c mice were subcutaneously injected with CT26 cells and when the tumor size reached 100 mm 3 , Methoxybenzoate, which is comparable to control (IP) injection in the case of treatment with octyl 4-hydroxy-3,5-dimethoxybenzoate (IP) (See FIG. 5D), as well as visually (see FIG. 5B), the growth rate of the tumor is greatly reduced.
  • IP control
  • the octyl 4-hydroxy-3,5-dimethoxybenzoate shows a decrease in tumor growth rate while increasing survival rate, while also less toxicity than other conventional chemotherapeutic methods.
  • the present invention has the effect of reducing cell viability by inducing cell cycle destruction and cell death of cancer cells specifically without affecting cell viability of normal cells, and thus can be usefully used in the field of cancer treatment.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Emergency Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention concerne un dérivé d'alkyle 4-hydroxy -3,5-dialcoxybenzoate qui a l'activité d'inhiber la croissance de cellules cancéreuses et de tuer des cellules cancéreuses avec l'induction de la mort cellulaire et une composition anticancéreuse le comprenant. Un composé et une composition selon la présente invention présentent l'effet de réduire la viabilité de cellules cancéreuses en induisant une interruption de cycle cellulaire et une apoptose spécifiquement dans des cellules cancéreuses sans affecter la viabilité de cellules normales.
PCT/KR2018/012350 2017-10-18 2018-10-18 Composition pharmaceutique pour un traitement anti-cancereux et procédé de préparation associé Ceased WO2019078645A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2017-0135325 2017-10-18
KR20170135325 2017-10-18
KR10-2018-0124248 2018-10-18
KR1020180124248A KR102142880B1 (ko) 2017-10-18 2018-10-18 항암치료용 약학 조성물 및 이의 제조방법

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005281164A (ja) * 2004-03-29 2005-10-13 Api Co Ltd 没食子酸エステル化合物、その製造方法、抗癌剤及び製剤
US20150313925A1 (en) * 2012-09-11 2015-11-05 Pontificia Universidad Javeriana Combination of compounds derived from gallic acid for the treatment of cancer
KR20170061562A (ko) * 2015-11-26 2017-06-05 주식회사 알엔에스 피부 상태개선용 조성물

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005281164A (ja) * 2004-03-29 2005-10-13 Api Co Ltd 没食子酸エステル化合物、その製造方法、抗癌剤及び製剤
US20150313925A1 (en) * 2012-09-11 2015-11-05 Pontificia Universidad Javeriana Combination of compounds derived from gallic acid for the treatment of cancer
KR20170061562A (ko) * 2015-11-26 2017-06-05 주식회사 알엔에스 피부 상태개선용 조성물

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CORDOVA, C. A. S. ET AL.: "Solid Lipid Nanoparticles Improve Octyl Gallate Antimetastatic Activity and Ameliorate Its Renal and Hepatic Toxic Effects", ANTICANCER DRUGS., vol. 28, no. 9, 1 October 2017 (2017-10-01), pages 977 - 988 *
NAKAMURA, E. S. ET AL.: "Cancer Chemopreventive Effects of Constituents of Caesalpinia Ferrea and Related Compounds", CANCER LETTERS, vol. 177, 2002, pages 119 - 124, XP002996965 *

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