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Oligonucleotide-selenide conjugate: Synthesis and its inducible sequence-specific alkylation of DNA |
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| Authors: | Yuhao Du Xiaocheng Weng Jing Huang Dan Zhang Heng Ma Dong Chen Xiang Zhou Jean-François Constant |
| Institution: | 1. College of Chemistry and Molecular Sciences, Minist Educ, Key Lab Biomed, Wuhan University, Hubei, Wuhan 430072, PR China;2. DCM-UMR 5250, ICMG-FR2607, Université Joseph Fourier, BP 53, 38041 Grenoble Cédex 9, France;3. State Key Laboratory of Bio-Organic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, PR China;4. State Key Laboratory of Natural and Biomimetic Drugs and State Key Laboratory of Applied Organic Chemistry, PR China |
| Abstract: | Oligonucleotide-selenium conjugate was designed and synthesized and its sequence-specific cross-linking ability was investigated. The selenide derivatives can generate covalent interstrand cross-linking with its complementary strand through the formation of o-QM intermediate induced by periodate oxidation. A cross-linking reaction yield of up to 50% was obtained. Hydroxyl radical footprinting experiment revealed that the quinone appendage specifically alkylated the cytosine base extending the duplex formed between the conjugate and the target strand. |
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