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首页> 外文期刊>Steroids: An International Journal >Photo-conversion of two epimers (20R and 20S) of pregna-5,7-diene-3beta, 17alpha, 20-triol and their bioactivity in melanoma cells.
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Photo-conversion of two epimers (20R and 20S) of pregna-5,7-diene-3beta, 17alpha, 20-triol and their bioactivity in melanoma cells.

机译：pregna-5,7-diene-3beta，17alpha，20-triol的两个差向异构体（20R和20S）的光转化及其在黑色素瘤细胞中的生物活性。

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Pregna-5,7-dienes and their hydroxylated derivatives can be formed in vivo when there is a deficiency in 7-dehydrocholesterol (7-DHC) Delta-reductase function, e.g., Smith-Lemli-Opitz syndrome (SLOS). Ultraviolet B (UVB) radiation induces photoconversion of 7-DHC to vitamin D3, lumisterol3 and tachysterol3. Two epimers (20R and 20S) of pregna-5,7-diene-3beta,17alpha,20-triol (4R and 4S, respectively) were synthesized and their UVB photo-conversion products identified as corresponding 9,10-secosteroids with vitamin D-like and tachysterol-like structures, and 5,7-dienes with inverted configuration at C-9 and C-10 (lumisterol-like). The number and character of the products and the dynamics of the process were dependent on the UVB dose. At high UVB doses, the formation of multiple oxidized derivatives of the primary products, and the formation of 5,7,9(11)-triene, were observed. The production of vitamin D-like, tachysterol-like and lumisterol-like derivatives was also observed in human skin treated with 4R and 4S, and subjected to UV irradiation, as shown by RP-HPLC. Newly synthesized compounds inhibited melanoma growth in dose dependent manner, and some of them showed equal or higher potency than 1,25(OH)2D3. In summary, we have characterized for the first time the products of UV induced conversion of pregna-5,7-diene-3beta,17alpha,20-triols and documented that the newly synthesized compounds have antiproliferative properties against melanoma cells.
机译：当7-脱氢胆固醇（7-DHC）Delta还原酶功能不足，例如史密斯-莱姆利-奥普茨综合征（SLOS）时，体内可形成Pregna-5,7-二烯及其羟基化衍生物。紫外线B（UVB）辐射可诱导7-DHC光转换为维生素D3，lumisterol3和tachysterol3。合成了pregna-5,7-diene-3beta，17alpha，20-triol（分别为4R和4S）的两种差向异构体（20R和20S），并将其UVB光转换产物鉴定为具有维生素D的相应9,10-secosteroids状和速甾醇状的结构，以及在C-9和C-10处具有颠倒构型的5,7-二烯（类卢固醇）。产品的数量和特性以及过程的动力学取决于UVB剂量。在高UVB剂量下，观察到初级产物的多种氧化衍生物的形成以及5,7,9（11）-三烯的形成。如RP-HPLC所示，在用4R和4S处理并经受紫外线照射的人皮肤中也观察到了维生素D样，速固醇样和lumisterol样衍生物的产生。新合成的化合物以剂量依赖性的方式抑制黑素瘤的生长，其中一些化合物显示出与1,25（OH）2D3相等或更高的效力。总之，我们首次表征了紫外线诱导的pregna-5,7-二烯-3beta，17alpha，20-三醇转化产物，并记录了新合成的化合物对黑素瘤细胞具有抗增殖特性。

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