WO2022265195A1 - Nouveau peptide antibactérien et son utilisation - Google Patents

Nouveau peptide antibactérien et son utilisation Download PDF

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Publication number
WO2022265195A1
WO2022265195A1 PCT/KR2022/004429 KR2022004429W WO2022265195A1 WO 2022265195 A1 WO2022265195 A1 WO 2022265195A1 KR 2022004429 W KR2022004429 W KR 2022004429W WO 2022265195 A1 WO2022265195 A1 WO 2022265195A1
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WIPO (PCT)
Prior art keywords
peptide
composition
present
porphyromonas gingivalis
oral
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PCT/KR2022/004429
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English (en)
Korean (ko)
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박준형
정호용
나타라잔사티시쿠마
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주식회사 쓰리빅스
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Publication of WO2022265195A1 publication Critical patent/WO2022265195A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/18—Peptides; Protein hydrolysates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids

Definitions

  • the present invention relates to novel antimicrobial peptides and uses thereof.
  • Antimicrobial peptides are mainly positively charged and have amphipathic properties due to hydrophobic amino acid residues. Due to this property, they bind to negatively charged microbial cell membrane lipids to change the potential of microbial cell membranes or to change the cell membrane potential. It destroys by puncturing or enters the cell membrane and inhibits cell function, thereby exhibiting antibacterial activity.
  • Antimicrobial peptides have proven effective against a wide range of pathogenic bacteria, fungi, parasites and viruses. Despite their excellent efficacy against pathogens, they have been rarely utilized until recently. Overuse or improper administration of classical antibiotics has caused serious problems in antimicrobial resistance. Thus, antimicrobial peptides can be considered as nature's alternative pharmacological resource against antibiotic-resistant microorganisms.
  • Periodontitis is an oral inflammatory disease caused by Gram-negative bacteria, particularly Porphyromonas gingivalis .
  • Treatment of periodontitis includes mechanical treatment such as scaling and antibiotics.
  • problems such as the appearance of antibiotic-resistant strains occur due to improper use of antibiotics. Therefore, there is a need for new therapeutic agents that can solve these problems and effectively treat oral diseases.
  • An object of the present invention is to provide a novel peptide having excellent antibacterial activity and an oral disease treatment composition using the same.
  • the present invention provides an antimicrobial peptide consisting of the amino acid sequence represented by SEQ ID NO: 1.
  • the present invention provides a polynucleotide encoding the antimicrobial peptide.
  • the present invention provides a pharmaceutical composition for preventing or treating oral diseases, a quasi-drug composition, and a health functional food composition comprising the antimicrobial peptide as an active ingredient.
  • the novel antibacterial peptide according to the present invention has excellent antibacterial activity against gram-negative bacteria or antibiotic-resistant bacteria related to oral diseases, and by using this, it can improve existing problems and more effectively prevent oral diseases such as tooth decay, periodontitis, and gingivitis, can be improved or cured.
  • MIC minimum inhibitory concentration
  • FIG. 2 is a graph showing the results of a cytotoxicity test according to an embodiment of the present invention.
  • the present inventors have synthesized a novel peptide, and the peptide is Porphyromonas gingivalis ( Porphyromonas gingivalis ), thereby completing the present invention.
  • the present invention provides an antimicrobial peptide consisting of the amino acid sequence represented by SEQ ID NO: 1.
  • peptide refers to a linear molecule formed by coupling amino acid residues to each other by a peptide bond.
  • the peptide is a synthetic peptide
  • the method for the synthesis may be a conventional chemical synthesis method of peptides in the art (W. H. Freeman and Co., Proteins; structures and molecular principles (1983)), specifically, a liquid phase solid phase method (Solution Phase Peptide Synthesis), Solid Phase Peptide Syntheses, Fragment Condensation Method, and F-moc or T-BOC Chemical Method, and more preferably, Liquid Phase Solid Phase Method (Merrifield, RB., J. Am. Chem Soc., 85.2149: 196), but is not limited thereto.
  • the peptide may have antibacterial activity against gram-negative bacteria, gram-positive bacteria, or antibiotic-resistant bacteria, preferably against gram-negative bacteria or antibiotic-resistant bacteria, and more preferably against gram-negative bacteria, but may have excellent antimicrobial activity, but is limited thereto It is not.
  • the gram-negative bacteria may be gram-negative bacteria of the genus Porphyromonas , and preferably, Porphyromonas gingivalis ( Porphyromonas gingivalis ), but is not limited thereto.
  • Porphyromonas gingivalis Porphyromonas gingivalis ; P. gingivalis )
  • P. gingivalis is one of several representative causative bacteria that cause oral diseases, and it has been reported that it occurs in the oral cavity where periodontal disease occurs, and is also found in the upper part of the gastrointestinal tract, respiratory tract and colon.
  • the gram-positive bacteria may be all gram-positive bacteria known in the art as gram-positive bacteria including Staphylococcus , Lactobacillus , and Bacillus , but are not limited thereto.
  • the antibiotic-resistant bacteria may be Porphyromonas gingivalis having antibiotic resistance, but is not limited thereto.
  • the antibiotics are aminoglycoside series (aminoglycoside, gentamicin, neomycin, etc.), penicillin series (ampicillin, etc.), sulfonamide series, beta-lactam series (beta-lactam, amoxicillin/clavulanic acid, etc.), chloramphenicol antibiotics of the antibiotic class, erythromycin class, florfenicol class, fosfomycin class, kanamycin class, lincomycin class, methicillin class, quinolone class, streptomycin class, tetracycline class, trimetsoprim class, and vancomycin class. It may be, but is not limited thereto.
  • the present invention provides a polynucleotide encoding the antimicrobial peptide.
  • the present invention provides a pharmaceutical composition for preventing or treating oral diseases comprising the antimicrobial peptide as an active ingredient.
  • the composition is Porphyromonas gingivalis ( Porphyromonas gingivalis ), it can be used as a pharmaceutical composition for the prevention or treatment of oral diseases caused by the strain.
  • the oral disease is various diseases occurring in the oral cavity, and may be one or more selected from the group consisting of tooth decay, periodontitis, and gingivitis, but is not limited thereto, and any disease occurring in the oral cavity may be included regardless of its condition.
  • the pharmaceutical composition according to the present invention can be prepared according to conventional methods in the pharmaceutical field.
  • the pharmaceutical composition may be formulated with an appropriate pharmaceutically acceptable carrier according to the formulation, and, if necessary, further include excipients, diluents, dispersants, emulsifiers, buffers, stabilizers, binders, disintegrants, solvents, etc. It can be manufactured by The appropriate carrier and the like do not inhibit the activity and characteristics of the antimicrobial peptide according to the present invention, and may be selected differently depending on the dosage form and formulation.
  • the pharmaceutical composition may be applied in any dosage form, and more specifically, it may be formulated and used in parenteral dosage forms such as oral dosage forms, external preparations, suppositories and sterile injection solutions according to conventional methods.
  • the solid dosage form is in the form of tablets, pills, powders, granules, capsules, etc., and includes at least one excipient such as starch, calcium carbonate, sucrose, lactose, sorbitol, mannitol, cellulose, gelatin, etc. may be prepared by mixing, and lubricants such as magnesium stearate and talc may be included in addition to simple excipients.
  • a liquid carrier such as fatty oil may be further included in addition to the above-mentioned materials.
  • liquid formulations include suspensions, solutions for internal use, emulsions, syrups, etc.
  • various excipients such as wetting agents, sweeteners, aromatics, and preservatives may be included. there is.
  • the parenteral formulation may include a sterilized aqueous solution, a non-aqueous solvent, a suspension, an emulsion, a lyophilized formulation, and a suppository.
  • Propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyl oleate may be used as non-aqueous solvents and suspending agents.
  • As a base for the suppository witepsol, macrogol, Tween 61, cacao butter, laurin fat, glycerogeratin, and the like may be used. It is not limited thereto, and all suitable agents known in the art may be used.
  • calcium or vitamin D 3 may be further added to the pharmaceutical composition according to the present invention to enhance therapeutic efficacy.
  • composition according to the present invention can be administered in a pharmaceutically effective amount.
  • pharmaceutically effective amount means an amount that is sufficient to treat a disease with a reasonable benefit/risk ratio applicable to medical treatment and does not cause side effects.
  • the effective dosage level of the pharmaceutical composition depends on the purpose of use, the patient's age, sex, weight and health condition, disease type, severity, drug activity, drug sensitivity, administration method, administration time, administration route and excretion rate, treatment Duration, combination, or factors including drugs used concurrently and other factors well known in the medical arts may be determined differently. For example, although not constant, generally 0.001 to 100 mg/kg, preferably 0.01 to 10 mg/kg, may be administered once or several times a day. The dosage is not intended to limit the scope of the present invention in any way.
  • the pharmaceutical composition may be administered to any animal that may develop oral disease, and the animal may include, for example, humans and primates as well as livestock such as cattle, pigs, horses, and dogs.
  • the pharmaceutical composition may be administered by an appropriate administration route according to the formulation form, and may be administered through various oral or parenteral routes as long as it can reach the target tissue.
  • the method of administration is not particularly limited, and is administered by conventional methods, such as, for example, oral, rectal or intravenous, intramuscular, skin application, subcutaneous, intraventricular inhalation, intrauterine dural or intracerebroventricular injection. It can be.
  • the pharmaceutical composition may be used alone for the prevention or treatment of oral diseases, or may be used in combination with surgery or other drug treatment.
  • the present invention provides a quasi-drug composition for preventing or improving oral diseases comprising the antimicrobial peptide as an active ingredient.
  • the composition is Porphyromonas gingivalis ( Porphyromonas gingivalis ), it can be used as a quasi-drug composition for preventing or improving oral diseases caused by the strain.
  • the oral disease may be one or more selected from the group consisting of tooth decay, periodontitis and gingivitis, but is not limited thereto.
  • quasi-drugs means textiles, rubber products or similar products used for the purpose of treating, alleviating, treating or preventing human or animal diseases;
  • Non-machines and similar items items corresponding to one of preparations used for sterilization, insecticide, and similar purposes to prevent infection, and the quasi-drug composition according to the present invention may preferably include a quasi-drug for oral use .
  • the quasi-drug composition may further include ingredients commonly used in oral quasi-drug compositions in addition to the active ingredient, for example, abrasives, wetting agents, binders, foaming agents, sweeteners, preservatives, active pharmaceutical ingredients, flavoring agents, coloring agents, solvents , brighteners, solubilizers or pH adjusting agents.
  • abrasives for example, wetting agents, binders, foaming agents, sweeteners, preservatives, active pharmaceutical ingredients, flavoring agents, coloring agents, solvents , brighteners, solubilizers or pH adjusting agents.
  • the quasi-drug composition may be prepared in any dosage form conventionally prepared in the art, and for example, toothpaste, mouthwash, mouthwash, gum, candy, oral spray, oral ointment, oral varnish, mouthwash, and It may have a formulation such as gum massage cream, but is not limited thereto.
  • the quasi-drug composition may be used alone or overlapping, or overlapping with other oral quasi-drug compositions other than the present invention.
  • the present invention provides a health functional food composition for preventing or improving oral diseases comprising the antimicrobial peptide as an active ingredient.
  • the composition is Porphyromonas gingivalis ( Porphyromonas gingivalis ), it can be used as a health functional food composition for preventing or improving oral diseases caused by the strain.
  • the oral disease may be one or more selected from the group consisting of tooth decay, periodontitis and gingivitis, but is not limited thereto.
  • the health functional food may be prepared in powder, granule, tablet, capsule, syrup or beverage for the purpose of preventing or improving oral diseases, and the form that the food can take It is not limited and may include all foods in a conventional sense.
  • beverages and various drinks, fruits and their processed foods (canned fruit, jam, etc.), fish, meat and their processed foods (ham, bacon, etc.), breads and noodles, cookies and snacks, dairy products (butter, cheese, etc.) ), etc.
  • food used as feed for animals may also be included.
  • the health functional food composition may be prepared by further including food additives (food additives) commonly used in the art and appropriate other auxiliary ingredients.
  • food additives food additives commonly used in the art and appropriate other auxiliary ingredients.
  • the suitability as the food additive can be determined according to the standards and standards for the item in accordance with the general rules of the Food Additive Code and general test methods approved by the Ministry of Food and Drug Safety, unless otherwise specified.
  • Examples of the items listed in the 'Food Additive Code' include, for example, chemical compounds such as ketones, glycine, calcium citrate, nicotinic acid, and cinnamic acid; natural additives such as persimmon pigment, licorice extract, crystalline cellulose, kaoliang pigment, and guar gum; mixed preparations such as sodium L-glutamate preparations, noodle-added alkali preparations, preservative preparations, and tar color preparations; and the like.
  • the other auxiliary ingredients include, for example, flavoring agents, natural carbohydrates, sweeteners, vitamins, electrolytes, colorants, pectic acid, alginic acid, organic acids, protective colloidal thickeners, pH adjusting agents, stabilizers, preservatives, glycerin, alcohols, carbonating agents, etc. may additionally contain.
  • natural carbohydrate monosaccharides such as glucose and fructose, disaccharides such as maltose and sucrose, polysaccharides such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol, and erythritol may be used.
  • natural sweeteners such as thaumatin and stevia extract or synthetic sweeteners such as saccharin and aspartame may be used.
  • the effective dose of the antibacterial peptide contained in the health functional food according to the present invention may be appropriately adjusted according to the purpose of use, such as preventing or improving oral diseases.
  • the composition has the advantage of using food as a raw material and has no side effects that can occur when taking general medicines for a long time, and has excellent portability, so it can be taken as an adjuvant for preventing or improving oral diseases.
  • the peptide was synthesized by a solid phase method using Fmoc (9-fluorenylmethoxycarbonyl) as a protecting group for the N ⁇ -amino group of an amino acid.
  • Rink Amide MBHA-Resin was used as a starting material for peptides with -NH 2 carboxyl terminals
  • Fmoc-amino acid-Wang Resin was used for peptides with carboxyl terminals -OH type as starting materials.
  • the elongation of the peptide chain by Fmoc-amino acid coupling was performed by the DCC (N-hydroxybenzotriazole (HOBt)-dicyclo-hexylcar-bodiimide) method.
  • DCC N-hydroxybenzotriazole (HOBt)-dicyclo-hexylcar-bodiimide
  • the Fmoc group was removed with a 20% piperidine/N-methylpyrrolidone (NMP) solution, washed several times with NMP and dichloromethane (DCM), and then nitrogen dried with gas
  • the molecular weight was calculated based on the sequence of the synthesized peptide, and the exact molecular weight was measured using a matrix assisted laser desorption ionization mass spectrometer (MALDI).
  • MALDI matrix assisted laser desorption ionization mass spectrometer
  • Example 2 Porphyromonas gingivalis ( Porphyromonas gingivalis ) Confirmation of antibacterial activity against
  • Example 2 After dissolving the peptide prepared in Example 1 in distilled water at a concentration of 1 mg/mL, a broth microdilution method assay was used to confirm the antibacterial activity.
  • Porphyromonas gingivalis ( Strain number: KCTC5352 ) was cultured for 24 hours, and then a certain amount of the culture solution was added to a new BHI (Brain Heart Infusion) liquid medium and cotton red blood cells. After diluting to 0.1 at OD600 with a spectrophotometer in a medium supplemented with 5%, the peptide and positive control, oxytetracycline, were treated at a concentration of 50 ⁇ g/mL to 100 ⁇ g/mL and then treated for 24 hours. cultured. After culturing, absorbance was measured at OD600.
  • BHI Brain Heart Infusion
  • the human keratin cell line HaCat cell line is a human epidermal cell, and was identified by culturing in an environment of 37° C., 5% CO 2 using DMEM medium containing 1% penicillin-streptomycin and 10% FBS. .
  • HaCaT was seeded at 3 ⁇ 10 5 /well using DMEM medium supplemented with 10% FBS in a 6-well cell culture plate and cultured for one day. Thereafter, the cells were washed with a serum-free medium, treated with the peptide at each concentration in the serum-free medium, and then cultured for 24 hours, and cell death was confirmed.

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Abstract

La présente invention concerne un nouveau peptide antibactérien et son utilisation et plus particulièrement, fournit un peptide antibactérien constitué d'une séquence d'acides aminés représentée par SEQ ID n° : 1, et une composition pharmaceutique, une composition quasi médicamenteuse et une composition alimentaire fonctionnelle de santé destinée à la prévention ou au traitement de maladies buccales, comprenant le peptide antibactérien utilisé comme principe actif. Le peptide antibactérien présente une excellente activité antibactérienne contre des bactéries gram négatives ou des bactéries résistantes aux antibiotiques liées aux maladies buccales et peut ainsi être utilisé pour prévenir, soulager ou traiter plus efficacement les maladies buccales.
PCT/KR2022/004429 2021-06-16 2022-03-29 Nouveau peptide antibactérien et son utilisation WO2022265195A1 (fr)

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KR1020210078173A KR102302983B1 (ko) 2021-06-16 2021-06-16 신규한 항균 펩타이드 및 이의 용도
KR10-2021-0078173 2021-06-16

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KR102302983B1 (ko) * 2021-06-16 2021-09-17 주식회사 쓰리빅스 신규한 항균 펩타이드 및 이의 용도

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US20130108575A1 (en) * 2009-01-06 2013-05-02 C3 Jian, Inc. Antibacterial and antifungal peptides
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KR20160049577A (ko) * 2014-10-27 2016-05-10 경희대학교 산학협력단 항균 펩타이드 헥사머를 포함하는 구강 질환 예방 및 치료용 약학적 조성물 및 이의 용도
KR102302983B1 (ko) * 2021-06-16 2021-09-17 주식회사 쓰리빅스 신규한 항균 펩타이드 및 이의 용도

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KR101249702B1 (ko) 2010-06-16 2013-04-05 주식회사 나이벡 항균 또는 항염증 활성을 가지는 펩타이드 및 이를 유효성분으로 함유하는 약제학적 조성물

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KR20160049577A (ko) * 2014-10-27 2016-05-10 경희대학교 산학협력단 항균 펩타이드 헥사머를 포함하는 구강 질환 예방 및 치료용 약학적 조성물 및 이의 용도
KR102302983B1 (ko) * 2021-06-16 2021-09-17 주식회사 쓰리빅스 신규한 항균 펩타이드 및 이의 용도

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