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Effects of Synthetic Pseudoceramides on Sphingosine Kinase Activity in F9-12 Cells
( Byeong Deog Park ),( Shin Hee Lee ),( Yong Moon Lee ),( Hwan Soo Yoo ),( Myung Yong Park ),( You Xun Jin ),( Kyong Oh Shin ),( Seikwan Oh ) 한국응용약물학회 2011 Biomolecules & Therapeutics(구 응용약물학회지) Vol.19 No.1
Sphingosine kinase (SPHK) has a central role to control cell death and cell proliferation, which is suggested as a sphingolipid rheostat by regulating the levels between ceramide and sphingosine 1-phosphate (S1P). Therefore, physiological regulators of SPHK will be a good candidate to develop a new targeted drug. For this purpose, a series of synthetic pseudoceramides were tested by SPHK assay either cell-based or cell-free system. K10PC-5 strongly inhibited SPHK, while K6PC-5 activated SPHK in cell-free system. Specifically, K6PC-5 activated SPHK under the co-treatment with 50 uM dimethylsphingosine (DMS), a SPHK inhibitor. Collectively, we developed a simple SPHK assay system to find SPHK regulatory pseudoceramide compounds, K10PC-5 and K6PC-5 which may be useful to cancer treatment or immune regulation like FTY720, a synthetic sphingolipid mimetic compound.
The Synthesis of New Pseudoceramides using Alkylketene Dimer and Their Physical Properties
Park, Byeong Deog,Lee, Myung Jin,Kim, Yoon,Lee, Jong Gi 한국공업화학회 1999 Journal of Industrial and Engineering Chemistry Vol.5 No.3
As cosmetic raw materials, novel pseudoceramides have been synthesized and their physical properties have been investigated. The pseudoceramides, PC-4 (N-(2,3-dihydroxypropyl)2-myristyl/palmityl-3-oxostearamide/arachidamide), and PC-5 (N-(1,3-dihydroxyisopropyl)-2-myristyl/palmityl3-oxostearamide/arachidamide), were synthesized according to the reaction between alkylketene dimer (AKD) and alkanolamines. The reduced types of new pseudoceramides, PC-4R (N-(2,3-dihydroxypropyl)-2-myristyl/palmityl-3-hydroxystearamide/arachidamide) and PC-5R (N-(1,3-dihydroxyisopropyl)2-myristyl/palmityl-3-hydroxystearamide/arachidamide) were prepared by the reduction of PC-4 and PC-5, respectively. An effective and economical synthetic pathway with high purity and high yield enabled the industrial production of these pseudoceramides. It was confirmed that there were several kinds of hydrogen bonding in them by the FT-IR study. X-ray diffraction (XRD) method and cross-polarized microscopy results make us confirm their intrinsic characteristics of lamellar structure formations. This intrinsic power to form the lamellar structure made it possible to form a pseudo-stratum corneum lipid emulsion, which shows the multi-lamellar structure.
Novel Pseudoceramides And Their Synthesis Using Alkyl Ketene Dimer
( Byeong-deog Park ),( Ki-mu Lee ),( Ik-ju Park ),( Young-jin Song ),( Jung-suk Lee ),( Myung-jin Lee ) 대한화장품학회 1997 대한화장품학회지 Vol.23 No.3
Nowadays, ceramides have been found to be an important component in the outermost layer of the skin - the stratum corneum. It is undersrood that ceramides play an important role in structure and maintenance of the interellular lipid lamella structure in the SC layer. Thus, many efforts have been made by the cosmetics and pharmaceutical industries to get human skin-identical ceramides or pseudoceramides which show similar performance with natural ceramides. The purpose of our study was to systhesize new pseudoceramides via an effective and economical systhetic pathway and to show their performance of skin restoratio. Four kinds of the new pseudoceramides were synthesized by the reaction of alcoholic amine and alkyl ketene dimer. First of all, PC-4 and PC-5 were synthesized by the reaction of 3-amino-1,2-propanidiol and serinol with alkyl ketene dimer respectively. After that, PC-4R and PC-5R were produced by changign kitone group at β-position to amide bond of above synthesized PC-4 and PC-5 into hydroxyl group using NaBH4 respectively. Their expected structures were conformed by the NMR, IR spectra, and elemental analysis. A study to show the restoration effectiveness was performed in which human skin was pretreated with high concentration of SDS surfactant solution. Using 0.5% solution of above synthesized pseudoceramides, there was the significantly faster restoration of the damaged than that of placebe itself treatment.
생체활성 각질층 지질 - 아토피 피부염 관리를 중심으로 -
박병덕 ( Byeong Deog Park ),염종경 ( Jong Kyung Youm ),안성구 ( Sung Ku Ahn ),이승헌 ( Seung Hun Lee ) 대한화장품학회 2004 대한화장품학회지 Vol.30 No.3
아토피 피부염을 설명하는 데는 두 가지 패러다임이 있는데, 첫 번째는 outside-inside paradigm이고 두 번째는 inside-ouside paradigm이다. Outside-inside paradigm에 의하면 아토피 피부염을 치료하기 위한 가장 좋은 방법은 피부 장벽 기능을 회복시키는 것이다. 장벽 기능은 각질층의 특징적인 구조에 의해 유지되는데, 각질층은 층상구조의 inter-cellular lipids와 corneocyte로 구성되어 있다. 아토피 피부염 환자, 층판상 어린선 환자의 각질층 내 층상구조는 hexagonal 구조가 많이 존재하고 있음을 보였으며, 이는 Ceramide 1 타입과 long chain fatty acid의 감소 때문이라고 보여진다. 이러한 이유에서 라멜라구조를 가지며 intercellular long periodicity phase 기능을 복원할 수 있는 보습제는 각질층의 intercellular lipid의 층상구조를 복원시킬 수 있을 것이다. 또한 세라마이드와 유사세라마이드를 함유한 보습제는 손상된 피부장벽, 피부질환, 아토피 피부염을 위한 유용한 치료제로 사용할 수 있다. Inside-outside paradigm에 따르면, 아토피 피부염 등이 보조 T cell, Ig E, eosinophil 등을 포함한 면역반응과 관계되는데, 특히 Th1/Th2 imbalance의 복원이 아토피 피부염을 치료하는데 효과적일 것이다. 현재 여러 종류의 면역억제제가 소개되고 있지만, 이들은 고유 면역기능을 감소시킬 우려를 가지고 있다. 따라서, 세라마이드 대사산물인 SPC와 S1P는 면역조절 기능 및 상처치유의 기능을 가짐으로써 향후 관심이 집중될 것이다. There are two paradigms to explain the atopic dermatitis. The first is outside-inside paradigm and the second is inside-outside paradigm. According to the outside-inside paradigm the best way to treat the atopic dermatitis is recovery of skin barrier function. The barrier function is maintained by the specific structure of stratum corneum, which is constructed from corneocytes and intercellular lipids. In terms of lipid structures of SC in atopic dermatitis and lamellar ichthyosis, they contain more fluid hexagonal gel structures in SC and show deficiencies in free fatty acids, especially long chains and certain ceramides. With this reason, moisturizer which has the lamellar structure and restoring function of intrinsic intercellualr long periodicity phase can maintain and restore the lamellar structure of intercellular lipids in SC. The moisturizers containing ceramide or pseudoceramide also seem to be reasonable therapy for atopic dermatitis and several skin diseases, which interrelated with impaired skin harrier. By the way, according to the inside-outside paradigm, immune response including helper T cells, IgE, eosinophils is related. It is effective treatment of atopic dermititis to restore imbalance between Th1 and Th2 cells. Even though several kinds of immune-suppressor were introduced, these can affect the intrinsic immune function. SPC and S1P, metabolites of ceramide, would be interesting because they have the function of wound healing and immune modulating properties.