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Diselenolane-mediated cellular uptake†
Chemical Science ( IF 7.6 ) Pub Date : 2018-01-17 00:00:00 , DOI: 10.1039/c7sc05151d Nicolas Chuard 1 , Amalia I Poblador-Bahamonde 1 , Lili Zong 1 , Eline Bartolami 1 , Jana Hildebrandt 2 , Wolfgang Weigand 2 , Naomi Sakai 1 , Stefan Matile 1
Chemical Science ( IF 7.6 ) Pub Date : 2018-01-17 00:00:00 , DOI: 10.1039/c7sc05151d Nicolas Chuard 1 , Amalia I Poblador-Bahamonde 1 , Lili Zong 1 , Eline Bartolami 1 , Jana Hildebrandt 2 , Wolfgang Weigand 2 , Naomi Sakai 1 , Stefan Matile 1
Affiliation
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The emerging power of thiol-mediated uptake with strained disulfides called for a move from sulfur to selenium. We report that according to results with fluorescent model substrates, cellular uptake with 1,2-diselenolanes exceeds uptake with 1,2-dithiolanes and epidithiodiketopiperazines with regard to efficiency as well as intracellular localization. The diselenide analog of lipoic acid performs best. This 1,2-diselenolane delivers fluorophores efficiently to the cytosol of HeLa Kyoto cells, without detectable endosomal capture as with 1,2-dithiolanes or dominant escape into the nucleus as with epidithiodiketopiperazines. Diselenolane-mediated cytosolic delivery is non-toxic (MTT assay), sensitive to temperature but insensitive to inhibitors of endocytosis (chlorpromazine, methyl-β-cyclodextrin, wortmannin, cytochalasin B) and conventional thiol-mediated uptake (Ellman's reagent), and to serum. Selenophilicity, the extreme CSeSeC dihedral angle of 0° and the high but different acidity of primary and secondary selenols might all contribute to uptake. Thiol-exchange affinity chromatography is introduced as operational mimic of thiol-mediated uptake that provides, in combination with rate enhancement of DTT oxidation, direct experimental evidence for existence and nature of the involved selenosulfides.
中文翻译：
二硒醇介导的细胞摄取†
硫醇介导的二硫化物吸收的新兴力量要求从硫转向硒。我们报告说，根据荧光模型底物的结果，就效率和细胞内定位而言，细胞对 1,2-二硒烷的摄取超过了对 1,2-二硫戊环和桥二硫二酮哌嗪的摄取。硫辛酸的二硒化物类似物表现最好。这种 1,2-二硒醇烷可有效地将荧光团递送至 HeLa京都细胞的细胞质，而不会像 1,2-二硫戊烷那样检测到内体捕获，也不会像桥二硫二酮哌嗪那样显着逃逸到细胞核中。二硒醇介导的胞质递送是无毒的（MTT 测定），对温度敏感，但对内吞抑制剂（氯丙嗪、甲基-β-环糊精、渥曼青霉素、细胞松弛素 B）和传统硫醇介导的摄取（埃尔曼试剂）不敏感，并且血清。亲硒性、0° 的极端 CSeSeC 二面角以及初级和次级硒醇的高但不同的酸度都可能有助于吸收。引入硫醇交换亲和层析作为硫醇介导的吸收的操作模拟，结合 DTT 氧化速率的增强，提供所涉及的硒硫化物的存在和性质的直接实验证据。
更新日期：2018-01-17
中文翻译：
二硒醇介导的细胞摄取†
硫醇介导的二硫化物吸收的新兴力量要求从硫转向硒。我们报告说，根据荧光模型底物的结果，就效率和细胞内定位而言，细胞对 1,2-二硒烷的摄取超过了对 1,2-二硫戊环和桥二硫二酮哌嗪的摄取。硫辛酸的二硒化物类似物表现最好。这种 1,2-二硒醇烷可有效地将荧光团递送至 HeLa京都细胞的细胞质，而不会像 1,2-二硫戊烷那样检测到内体捕获，也不会像桥二硫二酮哌嗪那样显着逃逸到细胞核中。二硒醇介导的胞质递送是无毒的（MTT 测定），对温度敏感，但对内吞抑制剂（氯丙嗪、甲基-β-环糊精、渥曼青霉素、细胞松弛素 B）和传统硫醇介导的摄取（埃尔曼试剂）不敏感，并且血清。亲硒性、0° 的极端 CSeSeC 二面角以及初级和次级硒醇的高但不同的酸度都可能有助于吸收。引入硫醇交换亲和层析作为硫醇介导的吸收的操作模拟，结合 DTT 氧化速率的增强，提供所涉及的硒硫化物的存在和性质的直接实验证据。
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