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Redox-Active Glycol Nucleic Acid (GNA) Components: Synthesis and Properties of the Ferrocenyl-GNA Nucleoside, Phosphoramidite, and Semicanonical Dinucleoside Phosphate
Organometallics ( IF 2.5 ) Pub Date : 2020-02-28 , DOI: 10.1021/acs.organomet.9b00851 Michał Piotrowicz 1 , Aleksandra Kowalczyk 2 , Damian Trzybiński 3 , Krzysztof Woźniak 3 , Konrad Kowalski 1
Organometallics ( IF 2.5 ) Pub Date : 2020-02-28 , DOI: 10.1021/acs.organomet.9b00851 Michał Piotrowicz 1 , Aleksandra Kowalczyk 2 , Damian Trzybiński 3 , Krzysztof Woźniak 3 , Konrad Kowalski 1
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Ferrocenylated glycol nucleic acid (Fc-GNA) components are rarely studied in the field of xeno nucleic acid (XNA) chemistry. As an attempt to contribute to XNA chemistry, in the present article we report a seven-step synthesis of the first semicanonical dinucleoside containing the Fc-GNA nucleoside linked to the adenosine nucleoside with a phosphodiester bond. First, the nucleoside-bearing ethynylferrocenyl moiety in the C5 position of the uracil nucleobase was obtained. In the following steps, the nucleoside was transformed into the phosphoramidite intermediate that in turn was reacted with N6-benzoyl-2′,3′-O-isopropylideneadenosine to afford the target dinucleoside phosphate with 47% yield. The newly obtained Fc-GNA nucleoside is redox-active, and on the basis of this property (function), it belongs to a new class of functional GNA (fun-GNA) nucleosides. The electrochemistry of the Fc-GNA nucleoside, dinucleoside phosphate, and ferrocenyl furanopyrimidone nucleoside that was obtained as an undesired byproduct of Fc-GNA nucleoside synthesis was investigated by cyclic voltammetry (CV). The CV result showed the presence of a one-electron ferrocenyl-centered redox wave in each case. The half-wave potentials of the Fc-GNA nucleoside and dinucleoside phosphate were 89 and 99 mV, respectively, against the FcH/FcH+ couple. Finally, the activity of the newly obtained Fc-GNA components was studied against the nontumorigenic mouse L929 and human cervix adenocarcinoma HeLa cells. The synthesized compounds showed no cytotoxic activity against the tested cell lines.
中文翻译：
氧化还原活性乙二醇核酸（GNA）成分：二茂铁基-GNA核苷，亚磷酰胺和半规范性双核苷磷酸酯的合成和性质
在异种核酸（XNA）化学领域中，很少研究二茂铁基化的二醇核酸（Fc-GNA）组分。为了促进XNA化学的发展，在本文中，我们报告了第一步的半规规二核苷的七步合成方法，该方法包含通过磷酸二酯键与腺苷核苷连接的Fc-GNA核苷。首先，获得在尿嘧啶核碱基的C5位上的具有核苷的乙炔基二茂铁基部分。在以下步骤中，将核苷转化为亚磷酰胺中间体，然后使其与N 6-苯甲酰基-2'，3'- O反应-异丙基腺苷腺苷以47％的产率提供目标磷酸二核苷。新获得的Fc-GNA核苷具有氧化还原活性，基于此特性（功能），它属于一类新的功能性GNA（fun -GNA）核苷。通过循环伏安法（CV）研究了作为Fc-GNA核苷合成的不良副产物获得的Fc-GNA核苷，磷酸二核苷和二茂铁基呋喃并嘧啶酮核苷的电化学。CV结果表明在每种情况下均存在以单电子二茂铁为中心的氧化还原波。Fc-GNA核苷和磷酸二核苷对FcH / FcH +的半波电势分别为89和99 mV。一对。最后，研究了新获得的Fc-GNA组分对非致瘤小鼠L929和人宫颈腺癌HeLa细胞的活性。合成的化合物对测试的细胞系没有细胞毒活性。
更新日期：2020-02-28
中文翻译：
氧化还原活性乙二醇核酸（GNA）成分：二茂铁基-GNA核苷，亚磷酰胺和半规范性双核苷磷酸酯的合成和性质
在异种核酸（XNA）化学领域中，很少研究二茂铁基化的二醇核酸（Fc-GNA）组分。为了促进XNA化学的发展，在本文中，我们报告了第一步的半规规二核苷的七步合成方法，该方法包含通过磷酸二酯键与腺苷核苷连接的Fc-GNA核苷。首先，获得在尿嘧啶核碱基的C5位上的具有核苷的乙炔基二茂铁基部分。在以下步骤中，将核苷转化为亚磷酰胺中间体，然后使其与N 6-苯甲酰基-2'，3'- O反应-异丙基腺苷腺苷以47％的产率提供目标磷酸二核苷。新获得的Fc-GNA核苷具有氧化还原活性，基于此特性（功能），它属于一类新的功能性GNA（fun -GNA）核苷。通过循环伏安法（CV）研究了作为Fc-GNA核苷合成的不良副产物获得的Fc-GNA核苷，磷酸二核苷和二茂铁基呋喃并嘧啶酮核苷的电化学。CV结果表明在每种情况下均存在以单电子二茂铁为中心的氧化还原波。Fc-GNA核苷和磷酸二核苷对FcH / FcH +的半波电势分别为89和99 mV。一对。最后，研究了新获得的Fc-GNA组分对非致瘤小鼠L929和人宫颈腺癌HeLa细胞的活性。合成的化合物对测试的细胞系没有细胞毒活性。
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