Synthesis of a new disulfide Fmoc monomer for creating biologically susceptible linkages in peptide nucleic acid oligomers |
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| Institution: | 1. College of Chemistry & Environment South China Normal University, Guangzhou 510006, China;2. Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;1. Department of Chemistry, Indiana University, Bloomington, Indiana;1. College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 34134, Republic of Korea;2. College of Pharmacy, Chungbuk National University, Cheongju 19421, Republic of Korea;1. School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, PR China;2. Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, PR China;3. Key Laboratory of Technology of Drug Preparation, Ministry of Education of China, Zhengzhou 450001, PR China;4. State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210023, Jiangsu, PR China |
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| Abstract: | Peptide nucleic acids (PNA) are one of many synthetic mimics of DNA and RNA that have found applications as biological probes, as nano-scaffold components, and in diagnostics. In an effort to use PNA as constructs for cellular delivery we investigated the possibility of installing a biologically susceptible disulfide bond in the backbone of a PNA oligomer. Here we report the synthesis of a new abasic Fmoc monomer containing a disulfide bond that can be incorporated into a PNA oligomer (DS-PNA) using standard solid phase peptide synthesis. The disulfide bond survives cleavage from the resin and DS-PNA forms duplexes with complementary PNA oligomers. Initial studies aimed at determining if the disulfide bond is cleavable to reducing agents while in a duplex are explored using UV thermal analysis and HPLC. |
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| Keywords: | Peptide nucleic acid Abasic site Disulfide cleavage Antisense |
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