RESUMO
The scope and limitation of Lubineau's reaction were evaluated for the synthesis of C-glycosides (compounds 1-13). Further transformation of side chain carbonyl was also achieved (compounds 16-23). Optimization of these two steps was investigated in xylose case. Some of the compounds were shown to stimulate sulfated glycosaminoglycans (GAGs) synthesis. Compound 20 (called Pro-Xylane) was identified as the best activator of GAGs biosynthesis. Pro-Xylane was developed using environmentally friendly conditions relevant to 'Green-Chemistry' principles and launched on the market in September 2006. This compound is the first example of 'Green' chemical used in cosmetic.
Assuntos
Química Farmacêutica/métodos , Glicosaminoglicanos/química , Glicosídeos/química , Álcoois/química , Carbono/química , Desenho de Fármacos , Humanos , Cetonas/química , Modelos Químicos , Proteoglicanas/química , Solventes/química , Temperatura , Água/química , Xilose/químicaRESUMO
NAD(+) dependent 15-hydroxyprostaglandin dehydrogenate (15-PGDH) catalyses oxidation of 15(S)-hydroxyl group of prostaglandins and as a result inactivates their physiological potential. Positive effects of prostaglandins or prostaglandin analogues were reported on terminal hair, vellus hair or eyelash growth and a complex prostaglandin network was recently described in human hair follicle. In the present study, we showed that 15-PGDH was expressed in human hair follicle mainly in melanocytes and keratinocytes, which brought us to consider this enzyme as a possible target to sustain local prostaglandin production. Using a recombinant enzymatic strategy, specific 15-PGDH inhibitors were screened. We identified a thiazolidine dione derivative exhibiting efficacy on follicular outer root sheath keratinocytes, since it concomitantly decreased the production of deactivated 13,14 dihydro 15-ketoprostaglandin F(2alpha) and sustained prostaglandin F(2alpha)in vitro production. In the context of recent interest in prostaglandins and prostaglandin analogues as hair regrowth agents, we postulated that the use of selected 15-PGDH inhibitors could reinforce or prolong the effect of these physiological mediators on hair and skin.
Assuntos
Regulação Enzimológica da Expressão Gênica , Folículo Piloso/citologia , Folículo Piloso/enzimologia , Hidroxiprostaglandina Desidrogenases/genética , Prostaglandinas/metabolismo , Biópsia , Western Blotting , Células Cultivadas , Clonagem Molecular , Inibidores Enzimáticos/farmacologia , Feminino , Humanos , Hidroxiprostaglandina Desidrogenases/antagonistas & inibidores , Hidroxiprostaglandina Desidrogenases/metabolismo , Queratinócitos/citologia , Queratinócitos/enzimologia , Melanócitos/citologia , Melanócitos/enzimologia , Pessoa de Meia-IdadeRESUMO
A logical precursor of macrocycle C60 H6 , cyclophane C60 H6 (CO)12 (1) represents a building block in a possible total synthesis of C60 . In Fourier transform ion cyclotron resonance laser desorption mass spectroscopic experiments in the negative-ion mode, 1 fragments to C60 H6 (2) under successive loss of CO. Further loss of six H atoms and rearrangement gives C60 ions with a fullerenic structure.