基于深穴偶氮杯［4］芳烃构筑的乏氧响应超分子水凝胶

姚顺雨; 蔡康; 郭东升

doi:10.11777/j.issn1000-3304.2022.22201

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基于深穴偶氮杯［4］芳烃构筑的乏氧响应超分子水凝胶

研究论文 | 更新时间：2024-10-08

- 基于深穴偶氮杯［4］芳烃构筑的乏氧响应超分子水凝胶
- A Hypoxia-responsive Supramolecular Hydrogel Based on a Deep-cavity Azocalix[4]arene
- 高分子学报 2022年53卷第10期页码：1271-1278
- 作者机构：
  
  1.南开大学，化学学院，天津 300071
  2.南开大学，功能高分子材料教育部重点实验室，天津 300071
  3.南开大学，元素有机化学国家重点实验室，天津 300071
- 作者简介：
  
  E-mail: kangcai@nankai.edu.cn
  dshguo@nankai.edu.cn
- 基金信息：
  
  国家自然科学基金(基金号 U20A20259);中央高校基本科研业务费专项资金和南开沧州渤海新区绿色化工研究有限公司基金资助项目
- DOI：10.11777/j.issn1000-3304.2022.22201
  中图分类号：
- 纸质出版日期：2022-10-20，
  
  网络出版日期：2022-08-11，
  
  收稿日期：2022-05-25，
  
  录用日期：2022-06-14
- 稿件说明：
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姚顺雨,蔡康,郭东升.基于深穴偶氮杯［4］芳烃构筑的乏氧响应超分子水凝胶[J].高分子学报,2022,53(10):1271-1278.

Yao Shun-yu,Cai Kang,Guo Dong-sheng.A Hypoxia-responsive Supramolecular Hydrogel Based on a Deep-cavity Azocalix[4]arene[J].ACTA POLYMERICA SINICA,2022,53(10):1271-1278.
姚顺雨,蔡康,郭东升.基于深穴偶氮杯［4］芳烃构筑的乏氧响应超分子水凝胶[J].高分子学报,2022,53(10):1271-1278. DOI： 10.11777/j.issn1000-3304.2022.22201.

Yao Shun-yu,Cai Kang,Guo Dong-sheng.A Hypoxia-responsive Supramolecular Hydrogel Based on a Deep-cavity Azocalix[4]arene[J].ACTA POLYMERICA SINICA,2022,53(10):1271-1278. DOI： 10.11777/j.issn1000-3304.2022.22201.

摘要

以

-乙胺基-4-氮杂环丁基-1

8-萘酰亚胺(EANA)染料客体接枝的透明质酸(HA)为水凝胶骨架，以乏氧响应的深穴偶氮杯[4

]

芳烃(CSAC4A)为交联剂

利用CSAC4A和EANA形成1:2主客体复合物的识别作用，制备了一种新型超分子水凝胶(HA-CA)，并对其形貌、力学性能和刺激响应性进行了表征和分析. 实验表明，当处于乏氧环境时，HA-CA中的CSAC4A能够发生响应断裂，物理交联点被破坏，释放出其中包裹的EANA染料，进而导致荧光信号恢复.

Abstract

Stimulus-responsive hydrogels based on host-guest interactions have attractive tremendous attentions in recent years

and have been applied successfully in a variety of research areas. Currently

a lot of macrocyclic hosts—such as cyclodextrin

crown ether

calixarenes

cucurbiturils

and pillararenes

etc

.—have been widely investigated in the preparation of stimulus-responsive supramolecular hydrogels. The major approach to introduce stimulus-responsive properties into these supramolecular hydrogels is exploiting specially designed guests which can response to external stimuli. However

most of functional guests—such as organic dyes—are fail to manifest stimulus-responsive properties

which is a big limitation for the development of functional host-guest supramolecular hydrogels. Introducing stimulus-responsive hosts with excellent guest-binding abilities as the building blocks of supramolecular hydrogels may be an efficient way to address this problem. Herein

hyaluronic acid (HA) was modified with

-ethylamino-4-azetidinyl-1

8-naphthalene anhydride (EANA) dyes and used as the polymeric backbone of the hydrogel

and a hypoxia-responsive

deep-cavity azocalix[4

]

arene (CSAC4A) was exploited as the noncovalent cross-linking agent. By utilizing the strong 1:2 recognition interactions between CSAC4A and the EANA moieties on the HA backbones

a new supramolecular hydrogel with hypoxia-responsiveness was prepared

and its morphology

mechanical properties

and hypoxia-responsive behavior were fully characterized. It has been showed that

the pore sizes of HA-CA are mainly distributed in the range of 40-70 μm

which indicates HA-CA is a typical microporous supramolecular hydrogel. Besides

the storage modulus (

') of HA-CA is stable at around 100 Pa

under the evaluation conditions of 0.5% strain

1 Hz. When HA-CA was put under a hypoxia environment

the azo bonds of CSAC4A were reduced and cleaved

leading to the release of the encapsulated EANA dyes

along with the recovery of their fluorescent emission. At the same time

due to the destruction of the physical cross-linking points

the cross-linked structure of the supramolecular hydrogel was destroyed

and its mechanical strength was significantly reduced. Therefore

HA-CA represents a novel type of hypoxia-responsive supramolecular hydrogel which might be potentially useful for biomedical applications.

关键词

超分子水凝胶主客体相互作用乏氧响应大环主体偶氮杯芳烃

Keywords

Supramolecular hydrogelHost-guest interactionHypoxia responseMacrocyclic hostAzocalix[4]arene

references

Kollman P A. Acc Chem Res, 1977, 10(10): 365-371. doi:10.1021/ar50118a003http://dx.doi.org/10.1021/ar50118a003

Ouyang G, Liu M. Mater Chem Front, 2020, 4(1): 155-167. doi:10.1039/c9qm00571dhttp://dx.doi.org/10.1039/c9qm00571d

Estroff L A, Hamilton A D. Chem Rev, 2004, 104(3): 1201-1218. doi:10.1021/cr0302049http://dx.doi.org/10.1021/cr0302049

Wojtecki R J, Meador M A, Rowan S J. Nat Mater, 2011, 10(1): 14-27. doi:10.1038/nmat2891http://dx.doi.org/10.1038/nmat2891

Chang G, Yang L, Yang J, Stoykovich M P, Deng X, Cui J, Wang D. Adv Mater, 2018, 30(7): 1704234. doi:10.1002/adma.201704234http://dx.doi.org/10.1002/adma.201704234

Tepper R, Bode S, Geitner R, Jäger M, Görls H, Vitz J, Dietzek B, Schmitt M, Popp J, Hager M D, Schubert U S. Angew Chem Int Ed, 2017, 56(14): 4047-4051. doi:10.1002/anie.201610406http://dx.doi.org/10.1002/anie.201610406

Voorhaar L, Hoogenboom R. Chem Soc Rev, 2016, 45(14): 4013-4031. doi:10.1039/c6cs00130khttp://dx.doi.org/10.1039/c6cs00130k

Yang Bo(杨勃), Sun Limei(孙立梅), Pan Yufan(潘玙璠), Dong Yuanchen(董原辰), Sun Yawei(孙亚伟), Liu Dongsheng(刘冬生). Acta Polymerica Sinica(高分子学报), 2021, 52(8): 996-1005. doi:10.11777/j.issn1000-3304.2021.21053http://dx.doi.org/10.11777/j.issn1000-3304.2021.21053

Amabilino D B, Smith D K, Steed J W. Chem Soc Rev, 2017, 46(9): 2404-2420. doi:10.1039/c7cs00163khttp://dx.doi.org/10.1039/c7cs00163k

Dong S, Zheng B, Wang F, Huang F. Acc Chem Res, 2014, 47(7): 1982-1994. doi:10.1021/ar5000456http://dx.doi.org/10.1021/ar5000456

Yan X, Liu Z, Zhang Q, Lopez J, Wang H, Wu H C, Niu S, Yan H, Wang S, Lei T, Li J, Qi D, Huang P, Huang J, Zhang Y, Wang Y, Li G, Tok J B H, Chen X, Bao Z. J Am Chem Soc, 2018, 140(15): 5280-5289. doi:10.1021/jacs.8b01682http://dx.doi.org/10.1021/jacs.8b01682

Zhou B, Jo Y H, Wang R, He D, Zhou X, Xie X, Xue Z. J Mater Chem A, 2019, 7(17): 10354-10362. doi:10.1039/c9ta01214ahttp://dx.doi.org/10.1039/c9ta01214a

Zhang X. Chinese J Polym Sci, 2022, (40): 541-542. doi:10.1007/s10118-022-2748-7http://dx.doi.org/10.1007/s10118-022-2748-7

Guo D S, Liu Y. Chem Soc Rev, 2012, 41(18): 5907-5921. doi:10.1039/c2cs35075khttp://dx.doi.org/10.1039/c2cs35075k

Ma X, Tian H. Acc Chem Res, 2014, 47(7): 1971-1981. doi:10.1021/ar500033nhttp://dx.doi.org/10.1021/ar500033n

Xia D, Wang L, Lv X, Chao J, Wei X, Wang P. Macromolecules, 2018, 51(7): 2716-2722. doi:10.1021/acs.macromol.8b00354http://dx.doi.org/10.1021/acs.macromol.8b00354

Liu Yuanxun(刘元勋),Liu Yang(刘洋), Yang Han(杨汉), Chen Lv(陈侣), Zhang Xiongzhi(张雄志), Liu Simin(刘思敏). Acta Polymerica Sinica(高分子学报), 2021, 52(10): 1361-1371. doi:10.11777/j.issn1000-3304.2021.21062http://dx.doi.org/10.11777/j.issn1000-3304.2021.21062

Manouras T, Vamvakaki M. Polym Chem, 2017, 8(1): 74-96. doi:10.1039/c6py01455khttp://dx.doi.org/10.1039/c6py01455k

Takashima Y, Hayashi Y, Osaki M, Kaneko F, Yamaguchi H, Harada A. Macromolecules, 2018, 51(12): 4688-4693. doi:10.1021/acs.macromol.8b00939http://dx.doi.org/10.1021/acs.macromol.8b00939

Tan C S Y, Liu J, Groombridge A S, Barrow S J, Dreiss C A, Scherman O A. Adv Funct Mater, 2018, 28(7): 1702994. doi:10.1002/adfm.201702994http://dx.doi.org/10.1002/adfm.201702994

Wang H, Zhu C N, Zeng H, Ji X ,Xie T, Yan X, Wu Z L, Huang F. Adv Mater, 2019, 31(12): 1807328. doi:10.1002/adma.201807328http://dx.doi.org/10.1002/adma.201807328

Zhou J, Yu G, Huang F. Chem Soc Rev, 2017, 46(22): 7021-7053. doi:10.1039/c6cs00898dhttp://dx.doi.org/10.1039/c6cs00898d

Zhu H, Shangguan L, Shi B, Yu G, Huang F. Mater Chem Front, 2018, 2(12): 2152-2174. doi:10.1039/c8qm00314ahttp://dx.doi.org/10.1039/c8qm00314a

Hou X, Chang Y X, Yue Y X, Wang Z H, Ding F, Li Z H, Li H B, Xu Y, Kong X, Huang F, Guo D S, Liu J. Adv Sci, 2022, 9(6): 2104349. doi:10.1002/advs.202104349http://dx.doi.org/10.1002/advs.202104349

Liu Q, Zhang T X, Zheng Y, Wang C, Kang Z, Zhao Y, Chai J, Li H B, Guo D S, Liu Y, Shi L. Small, 2021, 17(8): 2006223. doi:10.1002/smll.202006223http://dx.doi.org/10.1002/smll.202006223

Zhang T X, Hou X, Kong Y, Yang F, Yue Y X, Shah M R, Li H B, Huang F, Liu J, Guo D S. Theranostics, 2022, 12(1): 396-409. doi:10.7150/thno.67036http://dx.doi.org/10.7150/thno.67036

Zhang T X, Zhang Z Z, Yue Y X, Hu X Y, Huang F, Shi L, Liu Y, Guo D S. Adv Mater, 2020, 32(28): 1908435. doi:10.1002/adma.201908435http://dx.doi.org/10.1002/adma.201908435

Zhang Z, Yue Y X, Xu L, Wang Y, Geng W C, Li J J, Kong X L, Zhao X, Zheng Y, Zhao Y, Shi L, Guo D S, Liu Y. Adv Mater, 2021, 33(12): 2007719. doi:10.1002/adma.202007719http://dx.doi.org/10.1002/adma.202007719

Gutsche C D, Lin L G. Tetrahedron, 1986, 42(6): 1633-1640. doi:10.1016/s0040-4020(01)87580-3http://dx.doi.org/10.1016/s0040-4020(01)87580-3

Morita Y, Agawa T, Nomura E, Taniguchi H. J Org Chem, 1992, 57(13): 3658-3662. doi:10.1021/jo00039a027http://dx.doi.org/10.1021/jo00039a027

Liu X, Qiao Q, Tian W, Liu W, Chen J, Lang M J, Xu Z. J Am Chem Soc, 2016, 138(22): 6960-6963. doi:10.1021/jacs.6b03924http://dx.doi.org/10.1021/jacs.6b03924

Guo D S, Uzunova V D, Su X, Liu Y, Nau W M. Chem Sci, 2011, 2(9): 1722-1734. doi:10.1039/c1sc00231ghttp://dx.doi.org/10.1039/c1sc00231g

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