Photo-responsive DNA Hydrogel Based on Photoactive Thymine Phosphoramidite Monomer

Bo Yang; Li-mei Sun; Yu-fan Pan; Yuan-chen Dong; Ya-wei Sun; Dong-sheng Liu

doi:10.11777/j.issn1000-3304.2021.21053

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Photo-responsive DNA Hydrogel Based on Photoactive Thymine Phosphoramidite Monomer

Articles | 更新时间：2022-09-30

- Photo-responsive DNA Hydrogel Based on Photoactive Thymine Phosphoramidite Monomer
- ACTA POLYMERICA SINICA Vol. 52, Issue 8, Pages: 996-1005(2021)
- 作者机构：
  
  1.生命有机磷化学及化学生物学教育部重点实验室清华大学化学系北京 100084
  2.中国石油大学（华东）化学工程学院青岛 258000
  3.中国科学院化学研究所北京 100190
- 作者简介：
  
  Ya-wei Sun, E-mail: yawsun@upc.edu.cn
  Ya-wei Sun, E-mail: yawsun@upc.edu.cn
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2021.21053
  CLC：
- Published：20 August 2021，
  
  Published Online：29 June 2021，
  
  Received：19 February 2021，
  
  Revised：13 March 2021，
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杨勃,孙立梅,潘玙璠等.基于光敏性胸腺嘧啶脱氧核苷亚膦酰胺单体的光响应DNA水凝胶[J].高分子学报,2021,52(08):996-1005.

Yang Bo,Sun Li-mei,Pan Yu-fan,et al.Photo-responsive DNA Hydrogel Based on Photoactive Thymine Phosphoramidite Monomer[J].ACTA POLYMERICA SINICA,2021,52(08):996-1005.
杨勃,孙立梅,潘玙璠等.基于光敏性胸腺嘧啶脱氧核苷亚膦酰胺单体的光响应DNA水凝胶[J].高分子学报,2021,52(08):996-1005. DOI： 10.11777/j.issn1000-3304.2021.21053.

Yang Bo,Sun Li-mei,Pan Yu-fan,et al.Photo-responsive DNA Hydrogel Based on Photoactive Thymine Phosphoramidite Monomer[J].ACTA POLYMERICA SINICA,2021,52(08):996-1005. DOI： 10.11777/j.issn1000-3304.2021.21053.

摘要

设计并合成了一种1-(4

5-二甲氧基-2-硝基苄基)乙氧基光敏基团保护的胸腺嘧啶脱氧核苷亚膦酰胺单体，将其通过固相合成引入到DNA序列中，可以实现对DNA链互补配对的光学调控；并进一步利用该单体合成了功能性的核酸序列，成功制备了快速光响应的DNA超分子水凝胶. 该结果拓展了DNA单体的多样性，为构建新型光响应功能体系提供了新途径.

Abstract

Deoxyribonucleic acid (DNA) is a natural polyester polymer with programmable sequences and precise molecular recognition. Therefore

DNA has been widely investigated in functional devices and materials recently. Taking advantage of the structural diversity of DNA

novel functional devices and materials have been endowed with a variety of physical

chemical and biological responsiveness

among which

optical regulation has attracted much attention due to its non-contact and precise temporal-spatial controllability. To bring optical responsiveness to DNA material

it is necessary to introduce rational designed unnatural bases into DNA

which has been a challenging frontier. In this work

a novel thymine phosphoramidite monomer protected by 1-(4

5-dimethoxy-2-nitrobenzyl) ethoxy group (DMONB) has been designed and synthesized. The monomer was synthesized through 6 step reactions to shield the hydrogen bond site of thymine

and the product can be achieved in gram scale with high purity. Then the monomer was applied to synthesize photo-responsive DNA with random sequence through commercial solid phase synthesis procedure

which was purified and detected by RP-HPLC with good stability. The coupling efficiency of the photo-responsive monomer is comparable to the commercially available phosphoramidite monomers

detected by monitoring the 4

4'-dimethoxytriphenylmethyl (DMT) groups. The DMONB group could effectively hinder the DNA hybridization

which was demonstrated by the 10% native polyacrylamide gel electrophoresis. Under UV light for 30 s

the DMONB group could be totally removed and result in the recover of the DNA hybridization

which illustrates that this approach is of high efficiency and fast-responsive. Taking advantage of this controllable hybridization strategy

a fast light-responsive pure DNA supramolecular hydrogel has been designed and prepared

which could realize photo-chemically control the formation of pure DNA supramolecular hydrogel. This photo-induced DNA hydrogel exhibits 730 Pa storage modulus and 100 Pa loss modulus

with reversible thermal responsiveness and shear-thining property

which is similar to previously reported DNA hydrogel by our group. Our research expands the diversity of artificial DNA monomers and provides an alternative way to construct light-responsive functional DNA based materials system.

关键词

碱基光保护光响应DNA自组装DNA超分子水凝胶

Keywords

Nucleobase-cagingPhoto-responsivenessDNA self-assemblyDNA supramolecular hydrogel

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