KR101583866B1 - Composition for treating hyperpigmented skin diseases or for skin whitening containing 6-[N'-(3,4-Dihydroxy-benzylidene)-hydrazino]-pyridine-3-sulfonic acid diethylamide as a main ingredient - Google Patents
Composition for treating hyperpigmented skin diseases or for skin whitening containing 6-[N'-(3,4-Dihydroxy-benzylidene)-hydrazino]-pyridine-3-sulfonic acid diethylamide as a main ingredient Download PDFInfo
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Abstract
본 발명은 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드라는 성분을 유효성분으로 함유한 피부 미백용 조성물 내지 피부 과색소성 질환 예방, 치료 또는 개선용 조성물을 제공한다. 본 발명의 조성물은 멜라닌생성세포 내의 멜라노좀의 운반체인 멜라노필린과 미오신 5a 간의 결합을 억제하여, 멜라닌의 이동을 저해함으로써 우수한 미백효과를 나타내며, 멜라닌의 과다 축적으로 인한 피부 색소성 질환을 예방, 개선 또는 치료 효과를 나타낸다 . The present invention relates to a skin whitening composition comprising a component of 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide as an active ingredient, A composition for preventing, treating or ameliorating a disease. The composition of the present invention inhibits the binding between melanopyrin and myosin 5a, which is a carrier of melanocytes in melanin-producing cells, and inhibits the movement of melanin, thereby exhibiting an excellent whitening effect and preventing skin pigmentation caused by excessive accumulation of melanin, Improvement or therapeutic effect.
Description
본 발명은 피부 미백용 조성물 또는 피부 과색소성 질환 치료용 조성물에 관한 것이다. The present invention relates to a composition for whitening skin or a composition for treating skin hyperkeratotic disease.
멜라닌생성세포(melanocyte)의 멜라노좀(melanosome)은 자외선에 의한 세포의 파괴를 차단하는 기능을 갖는 멜라닌을 생성하는 세포내 소기관으로서, 각질형성세포로 이 소기관이 전달되어야만 피부에서 자외선에 의한 세포 손상을 최소화 시킬 수 있는 매우 중요한 요소이다.The melanosome of the melanocyte is an intracellular organelle that produces melanin that has the function of blocking the destruction of the cell by ultraviolet light. It is necessary to transfer this organelle to the keratinocyte, It is a very important factor that can minimize the number of
피부의 색을 조절하는 기전으로서, 멜라닌 생성의 화학적 및 효소적 기초에 대한 지식은 잘 알려져 있다. 멜라닌생성세포(melanocyte)는 멜라노좀(melanosome)이라는 소기관 내에서 멜라닌을 합성하고, 이 멜라노좀은 후에 멜라닌생성세포 덴드라이트(dendrites)를 통해 각질형성세포(케라티노사이트, keratinocyte)로 전달된다. 이렇게 각질형성세포로 전달된 멜라닌이 실제로 피부색을 결정하는 중요한 요소가 된다. 멜라노좀을 멜라닌생성세포의 덴드라이트로 이동시키는 데에는 주요 구성체들이 관여한다. 이들은 MTC(Melanosome transport complex)라고 불리며, 멜라노필린(Melanophilin), Rab27a 및 미오신(Myosin) 5a 세가지 단백질로 구성되어 있다. 상기 Rab27a는 멜라노좀의 표면에 결합하여 멜라노좀을 인지하고 이동시키는 운반체역할을 하는 단백질로서, 말단으로 이동하기 위해서는 세포내 세포골격(cytoskeleton)인 미오신 5a 단백질을 만나야 하며, 중간에서 이 두 단백질을 인지하고 연결시키는 어댑터(adapter)역할을 하는 것이 바로 멜라노필린(melanophilin)이라는 단백질이다.As a mechanism to regulate skin color, knowledge of the chemical and enzymatic basis of melanin production is well known. The melanocytes synthesize melanin in the organelles called melanosomes, which are then transferred to keratinocytes via melanin-producing cell dendrites. The melanin transferred to the keratinocyte is thus an important factor in determining the skin color. The major constituents involved in the transfer of melanomas to dendrites of melanin-producing cells. These are called MTC (Melanosome transport complex) and consist of three proteins: Melanophilin, Rab27a and Myosin 5a. Rab27a binds to the surface of melanosome and acts as a carrier to recognize and move the melanosome. To move to the end, it is necessary to meet myosin 5a protein, which is a cytoskeleton of the cell, It is a protein called melanophilin which acts as an adapter to recognize and connect.
이렇게 세 구성체가 만나 복합체(complex)를 이루면, 멜라노좀을 세포 말단으로 정상적으로 이동시키는 것이 가능하고, 궁극에는 각질형성세포로까지 전달이 가능해진다. 만일 이 세가지 구성체 중에 하나라도 이상이 있으면, 멜라닌의 생성에는 아무런 문제를 주지 않으면서도 멜라노좀의 이동에 문제가 생겨서, 결국에는 피부색이 밝아지는 현상이 관찰된다.When these three constituents meet and form a complex, it is possible to move the melanose normally to the cell end, and eventually to the keratinocyte. If any one of these three constituents is abnormal, there is a problem in the movement of the melanoma without any problem in the production of melanin, and eventually the skin color becomes bright.
본 발명은 멜라닌생성세포 내의 멜라노좀의 운반체인 멜라노필린과 미오신5a, 두 단백질간의 결합을 억제하여, 멜라닌의 이동을 저해함으로써 우수한 미백효과를 나타내는 피부 미백용 외용제 조성물을 제공하고자 한다.The present invention provides a composition for external skin application for skin whitening which exhibits excellent whitening effect by inhibiting binding between melanopyrin and myosin 5a, which are carriers of melanosomes in melanin-producing cells, and inhibiting the movement of melanin.
본 발명자들은 가상신약탐색 방법을 이용하여 멜라노필린 (Melanophilin)과 Rab27a의 결합저해를 통해 멜라노좀의 이동 억제를 위한 물질을 발굴하는 기술을 가지고 있으며, 이를 통해 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드 (6-[N'-(3,4-Dihydroxy-benzylidene)-hydrazino]-pyridine-3-sulfonic acid diethylamide)라는 화합물이 멜라닌생성세포 내에서 멜라노좀의 이동을 담당하는 운반체 단백질간의 결합을 억제함으로써 멜라노좀의 이동을 저해시키며, 이로 인해 멜라닌 합성 기능이 정상임에도 미백효능을 가질 수 있음을 발견하여 본 발명을 완성하였다. The present inventors have developed a technique for discovering a substance for inhibiting the movement of melanosomes through inhibition of binding of melanophilin and Rab27a using a novel novel drug detection method, thereby obtaining 6- [N '- (3,4 - dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide) was synthesized in the same manner as in Example 1, The compound inhibits the binding between the carrier proteins responsible for the transfer of melanosomes in the melanin-producing cells, thereby inhibiting the migration of melanosomes, thereby resulting in the whitening effect even though the melanin synthesis function is normal. Respectively.
본 발명은 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드라는 성분을 유효성분으로 함유한 피부 미백용 외용제 조성물을 제공한다. 더욱 상세하게는, 본 발명은 유효성분으로 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드를 함유함으로써 멜라닌생성세포 내의 멜라노좀의 운반체인 멜라노필린과 미오신 5a라는 두 단백질간의 결합을 억제하여, 멜라닌의 이동을 저해함으로써 우수한 미백효과를 나타내는 피부 미백용 외용제 조성물을 제공한다. The present invention provides a composition for external skin application for skin whitening comprising a component of 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide as an active ingredient . More particularly, the present invention relates to a method for producing melanin-producing melanocytes in a melanin producing cell by containing 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine- Provided is a composition for external application for skin whitening which inhibits the binding between two proteins, melanophilin and myosin 5a, which are carrier substances, and inhibits the movement of melanin, thereby exhibiting excellent whitening effect.
본 발명의 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드는 하기 화학식 1의 구조를 가진다. The 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide of the present invention has a structure represented by the following formula (1).
본 발명의 상기 화합물은 멜라닌생성세포내에서 멜라노좀의 이동을 담당하는 운반체 단백질인 멜라노필린과 Rab27a라는 단백질간의 결합을 억제함으로써 멜라노좀의 이동을 저해시켜, 이로 인해 멜라닌 합성 기능이 정상임에도 미백효능을 나타낸다.The compound of the present invention inhibits the binding of melanopyrin, which is a carrier protein responsible for the transfer of melanosomes in melanin-producing cells, to a protein called Rab27a, thereby inhibiting the movement of melanosomes, .
본 발명에 의한 피부 미백용 외용제 조성물은 유효성분으로 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드를 조성물 총 중량에 대하여 0.0001~10중량%, 바람직하게는 유효한 효과와 조성물의 안전성 및 제형 안정성을 고려하여 0.001~10중량%로 함유한다. 이는 0.001중량% 미만에서는 그 효과를 기대할 수 없고, 10중량% 초과에서는 조성물 안전성 및 제형 안정성에 어려움이 있기 때문이다.The composition for external application for skin whitening according to the present invention comprises 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide as an active ingredient, By weight, preferably 0.001 to 10% by weight, in consideration of effective effects, safety of the composition and stability of the formulation. If the amount is less than 0.001 wt%, the effect can not be expected. If the amount is more than 10 wt%, the composition stability and formulation stability are difficult.
상기 조성물은 용액, 현탁액, 유탁액, 페이스트, 겔, 크림, 로션, 파우더, 비누, 계면활성제-함유 클린싱,오일, 분말 파운데이션, 유탁액 파운데이션, 왁스 파운데이션 또는 스프레이 제형을 가진다. The composition may be a solution, suspension, emulsion, paste, gel, cream, lotion, powder, soap, surfactant-containing cleansing, oil, powder foundation, emulsion foundation, wax foundation or spray formulation.
본 발명은 또한 유효성분으로 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드를 함유하는, 멜라닌의 과다 축적으로 인한 피부 색소성 질환을 예방, 개선 또는 치료하기 위한 약학적 조성물을 제공한다. The present invention also relates to a method for the treatment of skin pigment caused by excessive accumulation of melanin, which comprises 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine- A pharmaceutical composition for preventing, ameliorating or treating a sexual disorder is provided.
멜라닌의 과다 축적으로 인한 피부 색소성 질환은 색소침착증, 예컨대, 주근깨, 유전성대측성색소이상증(遺傳性對側性色素異常症), 망상지단(網狀肢端)색소침착증, 모반(母斑), 예컨대, 편평(扁平)모반, 색소성모반 등과 같은 선천적 색소침착증, 및 기미, 노인성색소반 등과 같은 후천성 색소침착증 및, 유전적 피부 질환, 예를 들어, 백반, 바덴부르그 증후군, 후천적 피부 질환, 예를 들어, 후염증성 백색 비강진, 원인불명 물방울 멜라닌 저하증, 기미, 약물치료에 기인한 피부 질환, 예를 들어, 미노사이클린, 블레오마이신, 부술판, 지도부딘, 및 감염을 통해 전이된 피부 질환, 예를 들어, 어루러기 등을 포함한다. Skin pigmentation disorders due to excessive accumulation of melanin include, but are not limited to, pigmentation, such as freckles, hereditary dystrophychromatosis, reticuloendotheliopathy, For example, congenital indigestion such as flattened nevus, pigmented moths and the like and acquired pigmentation such as stain, senile pigment and the like, and genetic skin diseases such as albinism, Badenbürg syndrome, acquired skin disease, For example, skin diseases caused by postinflammatory white nasopharynx, undetermined melancholyesia, hypochromia, drug treatments such as minocycline, bleomycin, vesicopter, zidovudine, and skin diseases caused by infection, For example,
본 발명의 약학적 조성물은 유효성분인 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드에 추가로 약학적 조성물의 제조에 통상적으로 사용하는 적절한 담체, 부형제 및 희석제를 더 포함하여 제형화될 수 있으며, 각각 통상의 방법에 따라 산제, 과립제, 정제, 캡슐제, 현탁액, 에멀젼, 시럽, 에어로졸 등의 경구형 제형, 외용제, 좌제 및 멸균 주사용액의 형태로 제형화될 수 있으며, 가장 바람직한 제형은 외용제이다. 제제화에 관한 내용은 Remington's Pharmaceutical Science(최근판), Mack Publishing Company, Easton PA 등의 문헌을 참조할 수 있다. The pharmaceutical composition of the present invention can be used in addition to the active ingredient 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide The pharmaceutical composition of the present invention may further comprise an appropriate carrier, excipient and diluent which are conventionally used, and may be formulated in accordance with a usual manner into oral formulations such as powders, granules, tablets, capsules, suspensions, emulsions, syrups and aerosols, Suppositories, and sterile injectable solutions. The most preferred formulations are external preparations. For formulation information, see Remington's Pharmaceutical Science (recent edition), Mack Publishing Company, Easton PA et al.
본 발명에 따른 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드의 바람직한 투여량은 환자의 상태 및 체중, 질병의 정도, 약물형태, 투여경로 및 기간에 따라 다르지만, 당업자에 의해 적절하게 선택될 수 있다. 그러나 바람직한 효과를 위해서, 1일 0.0001 내지 100 mg/kg으로, 바람직하게는 0.001 내지 10 mg/kg으로 투여하는 것이 좋다. 투여는 하루에 한번 투여할 수도 있고, 수회 나누어 투여할 수도 있다. 상기 투여량은 어떠한 면으로든 본 발명의 범위를 한정하는 것은 아니다.The preferred dosage of the 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide according to the present invention depends on the condition and weight of the patient, The mode of administration, the route of administration, and the period of time, but can be appropriately selected by those skilled in the art. However, in order to obtain the desired effect, it is preferable to administer it at 0.0001 to 100 mg / kg, preferably 0.001 to 10 mg / kg per day. The administration may be carried out once a day or divided into several times. The dose is not intended to limit the scope of the invention in any way.
이하, 실시예 및 실험예를 들어 본 발명을 보다 상세히 설명하지만, 본 발명이 이들 예로만 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to Examples and Experimental Examples, but the present invention is not limited thereto.
본 발명의 유효성분인 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드는 멜라닌생성세포 내의 멜라노좀의 운반체인 멜라노필린과 미오신 5a라는 두 단백질간의 결합을 억제하여, 멜라닌의 이동을 저해함으로써 우수한 미백효과를 나타내며, 멜라닌의 과다 축적으로 인한 피부 색소성 질환을 예방, 개선 또는 치료 효과를 나타낼 수 있다. The effective ingredient of the present invention, 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide is melanopyrin, which is a carrier of melanosomes in melanin- It inhibits the binding between two proteins called myosin 5a, inhibits the movement of melanin, thereby exhibiting an excellent whitening effect and exhibiting an effect of preventing, ameliorating or treating skin pigmentation diseases due to excessive accumulation of melanin.
도 1(a)는 Rab 27a와 멜라노필린의 결합 구조 모델링을 나타낸 도이고, 도 1(b)는 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드의 결합 구조 모델링을 나타낸 도이다.
도 2는 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드에 의한 멜라닌생성세포에서 멜라닌 이동 저해 효과를 확인한 도이다. FIG. 1 (a) is a diagram showing the binding structure modeling between Rab 27a and melanopyrin, and FIG. 1 (b) 3-sulfonic acid diethylamide. ≪ / RTI >
FIG. 2 is a graph showing the effect of inhibiting melanin migration in melanin-producing cells by 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide.
이하, 본 발명을 실시예 및 시험예를 통하여 더욱 상세히 설명한다. 그러나 이들 실시예 및 시험예는 본 발명을 예시하기 위한 것으로, 본 발명의 범위가 이들 실시예 및 시험예에 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail through examples and test examples. However, these examples and test examples are for illustrating the present invention, and the scope of the present invention is not limited to these examples and test examples.
[실험예 1] 분자 모델링을 이용한 단백질 3차 구조 결정 및 리간드 결정[Experimental Example 1] Determination of protein tertiary structure and determination of ligand using molecular modeling
단백질 3차 구조 모델링을 통하여, Rab 27a와 멜라노필린의 결합 구조 모델링하여 도 1(a)에 나타내고, 여기에 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노-피리딘-3-술폰산 디에틸아미드의 결합을 모델링하여 도 1(b)에 나타내었다. The binding structure of Rab 27a and melanopyrin was modeled through protein tertiary structure modeling, which is shown in Fig. 1 (a), and 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino- Pyridine-3-sulfonic acid diethylamide was modeled as shown in Fig. 1 (b).
[실험예 2] 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드에 의한 멜라노좀 이동 억제 효과 확인Experimental Example 2 Confirmation of Melanosomal Inhibitory Effect by 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide
(1) 멜라닌 생성세포의 배양(1) Culture of melanin-producing cells
쥐의 불멸화된 멜라닌 생성세포인 멜란-a(Melan-a) 세포를 10% 우태아혈청(fetal bovine serum)이 포함된 RPMI 1640 배지에서, 3일에 한번씩 배지를 교환하면서 90% 점유율(confluency)을 보일 때까지 10% CO2 배양기에서 배양하였다.Melan-a cells, an immortalized melanocyte-producing cell of rats, were cultured in RPMI 1640 medium containing 10% fetal bovine serum for 90% confluency, until you see the the cells were cultured at 10% CO 2 incubator.
(2) 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드에 의한 멜라닌생성세포에서 멜라닌 이동 저해 확인(2) Confirmation of inhibition of melanin migration in melanin-producing cells by 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide
상기 (1) 단계에서 배양된 멜란-a(melan-a) 세포를 0.25% 트립신(Trypsin)-EDTA로 떼어내고, 24-배양용기(well-plate)에 다시 동일한 숫자(1×105 cells/well)로 깔은 후에 24시간 동안 배양하였다. 여기에 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드를 3가지 농도로 처리하고, 3일 후에 광학현미경을 통해 세포모양을 관찰하였으며, 결과는 도 2에 나타내었다.The melan-a cells cultured in the above step (1) were removed with 0.25% trypsin-EDTA and the same number (1 x 10 5 cells / well) was added to the 24- well) and cultured for 24 hours. After treatment with 3 concentrations of 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide, And the results are shown in Fig.
도 2에서 보는 바와 같이, 검게 보이는 것이 멜라노좀으로 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드를 처리하지 않은 대조군과 비교하여, 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드를 처리한 세포에서는 멜라노좀이 세포 전체적으로 고루 분포하지 못하고, 핵 주변으로 몰려 있음을 확인할 수 있었다. As shown in FIG. 2, the dark black color was observed in the control group not treated with 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine- In comparison, in the cells treated with 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide, melanosomes were not distributed throughout the cell, And it was confirmed that they were gathered around.
(3) 정량화(3) Quantification
상기 (2) 단계에서 현미경을 통해 관찰한 멜라닌이동이 저해된 세포사진을 동일한 면적하에서 멜라닌이동이 저해된 세포의 숫자를 계수하여 아래 표 1로 나타내었다. The number of cells in which melanin migration was inhibited under the same area was counted by the cell photograph in which the melanin migration inhibition observed through the microscope in the step (2) was counted.
[표 1][Table 1]
이렇게 정량화된 숫자를 통하여 6-[N'-(3,4-디히드록시-벤질리덴)-히드라지노]-피리딘-3-술폰산 디에틸아미드를 처리한 세포가 대조군에 비해 멜라닌이동이 저해된 숫자가 더 많음을 알수 있었다. Cells treated with 6- [N '- (3,4-dihydroxy-benzylidene) -hydrazino] -pyridine-3-sulfonic acid diethylamide via these quantified digits were found to have inhibited melanin migration I could see that there were more numbers.
Claims (5)
The method according to any one of claims 1 to 3, further comprising the step of selecting a solution, suspension, emulsion, paste, gel, cream, lotion, powder, soap, surfactant-containing cleansing, oil, powder foundation, emulsion foundation, wax foundation or spray Wherein the composition is any one of the formulations.
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