ACS Publications. Most Trusted. Most Cited. Most Read

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Appl. Mater. Interfaces 2018, 10, 36, 30071-30080
RETURN TO ISSUEPREVResearch ArticleNEXT

Enhanced Release of Molecules upon Ultraviolet (UV) Light Irradiation from Photoresponsive Hydrogels Prepared from Bifunctional Azobenzene and Four-Arm Poly(ethylene glycol)

  • Shiva K. Rastogi*
    Shiva K. Rastogi
    Department of Chemistry and Biochemistry, Texas State University, San Marcos, Texas 78666, United States
    *E-mail: [email protected]
    More by Shiva K. Rastogi
    Orcidhttp://orcid.org/0000-0002-1589-6124
  • , 
  • Hailee E. Anderson
    Hailee E. Anderson
    Department of Chemistry and Biochemistry, Texas State University, San Marcos, Texas 78666, United States
    More by Hailee E. Anderson
  • , 
  • Joseph Lamas
    Joseph Lamas
    Department of Mechanical Engineering and Materials Science, Duke University, Durham, North Carolina 27708, United States
    More by Joseph Lamas
  • , 
  • Scott Barret
    Scott Barret
    Department of Chemistry and Biochemistry, Texas State University, San Marcos, Texas 78666, United States
    More by Scott Barret
  • , 
  • Travis Cantu
    Travis Cantu
    Materials Science, Engineering, and Commercialization Program, Texas State University, San Marcos, Texas 78666, United States
    More by Travis Cantu
  • , 
  • Stefan Zauscher
    Stefan Zauscher
    Department of Mechanical Engineering and Materials Science, Duke University, Durham, North Carolina 27708, United States
    More by Stefan Zauscher
    Orcidhttp://orcid.org/0000-0002-2290-7178
  • , 
  • William J. Brittain
    William J. Brittain
    Department of Chemistry and Biochemistry, Texas State University, San Marcos, Texas 78666, United States
    More by William J. Brittain
  • , and 
  • Tania Betancourt
    Tania Betancourt
    Department of Chemistry and Biochemistry, Texas State University, San Marcos, Texas 78666, United States
    Materials Science, Engineering, and Commercialization Program, Texas State University, San Marcos, Texas 78666, United States
    More by Tania Betancourt
    Orcidhttp://orcid.org/0000-0002-2460-6133
Cite this: ACS Appl. Mater. Interfaces 2018, 10, 36, 30071–30080
Publication Date (Web):February 21, 2017
https://doi.org/10.1021/acsami.6b16183
Copyright © 2017 American Chemical Society
Request reuse permissions

    Article Views

    4601

    Altmetric

    -

    Citations

    40
    LEARN ABOUT THESE METRICS
    Read OnlinePDF (10 MB)
    Get e-Alerts
    Supporting Info (1)»
    SUBJECTS:

    Abstract

    Abstract Image

    Advances in biosensors and drug delivery are dependent on hydrogels that respond to external stimuli. In this work, we describe the preparation and characterization of photoresponsive hydrogels prepared by cross-linking of di-NHS ester of azobenzoic acid and four-armed, amine-terminated poly(ethylene glycol). The porous structure and composition of the hydrogels were confirmed by scanning electron microscopy (SEM) and Fourier transform infrared (FTIR) spectroscopy. The reversible photoisomerization of the azobenzene-containing hydrogel cross-linkers in the gels was confirmed by absorption spectroscopy. Specifically, the photoisomerization of the cross-linkers between their trans and cis configurations was observed by monitoring the absorbance of the hydrogels at the two characteristic peaks of azobenzene (π–π* at 330 nm and n–π* at 435 nm). The effect of photoisomerization on the hydrogel structure was investigated by microscopy. Ultraviolet (UV) irradiation-induced reduction in hydrogel size was observed, which may be a result of the inherently smaller footprint of the cis azobenzene conformation, as well as dipole–dipole interactions between the polar cis azobenzene and the polymer network. The UV-triggered reduction in hydrogel size was accompanied by enhanced release of the near-infrared fluorescent dye Alexa Fluor 750 (AF750). Enhanced release of AF750 was observed in samples irradiated with UV versus dark control. Together, these data demonstrate the potential of these systems as reversible photoresponsive biomaterials.

    KEYWORDS:

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acsami.6b16183.

    • Figures S1–S7 (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 40 publications.

    1. Anna Tverdokhlebova, Ilya Sterin, Costel C. Darie, Evgeny Katz, Oleh Smutok. Stimulation–Inhibition of Protein Release from Alginate Hydrogels Using Electrochemically Generated Local pH Changes. ACS Applied Materials & Interfaces 2022, 14 (51) , 57408-57418. https://doi.org/10.1021/acsami.2c17914
    2. Xiaoqiang Xue, Kang Liang, Wenyan Huang, Hongjun Yang, Li Jiang, Qimin Jiang, Tao Jiang, Binzhe Lin, Yangjing Chen, Bibiao Jiang, Sridhar Komarneni. Molecular Engineering of Injectable, Fast Self-Repairing Hydrogels with Tunable Gelation Time: Characterization by Diffusing Wave Spectroscopy. Macromolecules 2022, 55 (15) , 6474-6486. https://doi.org/10.1021/acs.macromol.2c00899
    3. Zhiyong Zhao, Rui Yan, Michael Zharnikov. The Effect of Ultraviolet Light on Biorepulsive Hydrogel Poly(ethylene glycol) Films. ACS Applied Polymer Materials 2021, 3 (7) , 3446-3454. https://doi.org/10.1021/acsapm.1c00381
    4. Laura Chambre, Rachael N. Parker, Benjamin J. Allardyce, Filippo Valente, Rangam Rajkhowa, Rodney J. Dilley, Xungai Wang, David L. Kaplan. Tunable Biodegradable Silk-Based Memory Foams with Controlled Release of Antibiotics. ACS Applied Bio Materials 2020, 3 (4) , 2466-2472. https://doi.org/10.1021/acsabm.0c00186
    5. Adrianne M. Rosales, Christopher B. Rodell, Minna H. Chen, Matthew G. Morrow, Kristi S. Anseth, Jason A. Burdick. Reversible Control of Network Properties in Azobenzene-Containing Hyaluronic Acid-Based Hydrogels. Bioconjugate Chemistry 2018, 29 (4) , 905-913. https://doi.org/10.1021/acs.bioconjchem.7b00802
    6. Zheng Wu, Rongrong Xue, Mengqi Xie, Xuejiao Wang, Zihao Liu, Markus Drechsler, Jianbin Huang, and Yun Yan . Self-Assembly-Triggered Cis-to-Trans Conversion of Azobenzene Compounds. The Journal of Physical Chemistry Letters 2018, 9 (1) , 163-169. https://doi.org/10.1021/acs.jpclett.7b03060
    7. Tianhao Wang, Feixue Gao, Yan Zhang, Shaohua Wang, Xinjin Li, Zengdian Zhao, Yunhui Dong, Xiangye Li. Construction of multiresponsive supramacromolecular hydrogels with a novel azobenzene derivative as crosslinkers. Journal of Materials Research and Technology 2023, 22 , 1781-1790. https://doi.org/10.1016/j.jmrt.2022.11.178
    8. Yanghui Xing, Buhui Zeng, Wang Yang. Light responsive hydrogels for controlled drug delivery. Frontiers in Bioengineering and Biotechnology 2022, 10 https://doi.org/10.3389/fbioe.2022.1075670
    9. Siddhi S. Panchal, Dilip V. Vasava. Fabricating approaches for synthesis of miktoarm star-shaped polymers having tailored biodegradability. International Journal of Polymeric Materials and Polymeric Biomaterials 2022, 71 (18) , 1407-1424. https://doi.org/10.1080/00914037.2021.1981319
    10. Ronaldo Badenhorst, Oleh Smutok, Evgeny Katz. Recent Trends in Sense‐and‐Release Platforms Employing Electrochemically‐Triggered Payload (Drugs) Release – A Review. ChemElectroChem 2022, 9 (22) https://doi.org/10.1002/celc.202200897
    11. Nicolas Muzzio, Manuel Eduardo Martinez-Cartagena, Gabriela Romero. Soft nano and microstructures for the photomodulation of cellular signaling and behavior. Advanced Drug Delivery Reviews 2022, 190 , 114554. https://doi.org/10.1016/j.addr.2022.114554
    12. Sohini Bhattacharyya, Tapas Kumar Maji. Multi-dimensional metal-organic frameworks based on mixed linkers: Interplay between structural flexibility and functionality. Coordination Chemistry Reviews 2022, 469 , 214645. https://doi.org/10.1016/j.ccr.2022.214645
    13. Ronaldo Badenhorst, Evgeny Katz, Oleh Smutok. Electrochemically stimulated protein release from pH–switchable electrode–immobilized nitroavidin–biotin and avidin–iminobiotin systems. Physical Chemistry Chemical Physics 2022, 24 (33) , 19687-19692. https://doi.org/10.1039/D2CP02112A
    14. Feixue Gao, Zixuan Bi, Shaohua Wang, Zengdian Zhao, Yunhui Dong, Xiangye Li. An amphiphilic azobenzene derivative as a crosslinker in the construction of smart supramacromolecular hydrogels. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2022, 647 , 129088. https://doi.org/10.1016/j.colsurfa.2022.129088
    15. Yuan Zhou, Guiting Liu, Shaoyun Guo. Advances in ultrasound-responsive hydrogels for biomedical applications. Journal of Materials Chemistry B 2022, 10 (21) , 3947-3958. https://doi.org/10.1039/D2TB00541G
    16. Zahra Mazidi, Sanaz Javanmardi, Seyed Morteza Naghib, Zahra Mohammadpour. Smart stimuli-responsive implantable drug delivery systems for programmed and on-demand cancer treatment: An overview on the emerging materials. Chemical Engineering Journal 2022, 433 , 134569. https://doi.org/10.1016/j.cej.2022.134569
    17. Ronaldo Badenhorst, Vasantha Krishna Kadambar, Madhura Bellare, Artem Melman, Evgeny Katz, Oleh Smutok. Electrochemically produced local pH changes stimulating (bio)molecule release from pH-switchable electrode-immobilized avidin–biotin systems. Physical Chemistry Chemical Physics 2022, 24 (11) , 6410-6414. https://doi.org/10.1039/D2CP00689H
    18. Sheila Maiz-Fernández, Leyre Pérez-Álvarez, Unai Silván, José Luis Vilas-Vilela, Senentxu Lanceros-Méndez. pH-Induced 3D Printable Chitosan Hydrogels for Soft Actuation. Polymers 2022, 14 (3) , 650. https://doi.org/10.3390/polym14030650
    19. Rogelio Rodríguez-Rodríguez, Hugo Espinosa-Andrews, Zaira Yunuen García-Carvajal. Stimuli-Responsive Hydrogels in Drug Delivery. 2022, 75-103. https://doi.org/10.1007/978-981-16-7152-4_3
    20. Zhisen Wang, Yueshan Li, Xiaoyu Wang, Menghan Pi, Bin Yan, Rong Ran. A rapidly responsive, controllable, and reversible photo-thermal dual response hydrogel. Polymer 2021, 237 , 124344. https://doi.org/10.1016/j.polymer.2021.124344
    21. Cong Liu, Zhongbin Xu, Junfeng Liu, Xing Huang, Yan Shan. Enabling direct dense encapsulation of water-insoluble powder in hydrogel microcapsules by bubble-assisted encapsulation method. Materials & Design 2021, 209 , 109952. https://doi.org/10.1016/j.matdes.2021.109952
    22. Ying Zhang, Hongfang Du, Panpan He, Chuang Shen, Qi Li, Yefan Duan, Zhouwei Shao, Fei Mu, Feng Huang, Peiyang Li, Pingqi Gao, Peng Yu, Zhimin Luo, Lianhui Wang. Exfoliated FePS3 nanosheets for T1-weighted magnetic resonance imaging-guided near-infrared photothermal therapy in vivo. Science China Materials 2021, 64 (10) , 2613-2623. https://doi.org/10.1007/s40843-021-1633-5
    23. Sven Schultzke, Melanie Walther, Anne Staubitz. Active Ester Functionalized Azobenzenes as Versatile Building Blocks. Molecules 2021, 26 (13) , 3916. https://doi.org/10.3390/molecules26133916
    24. Hong‐Bo Cheng, Shuchun Zhang, Ji Qi, Xing‐Jie Liang, Juyoung Yoon. Advances in Application of Azobenzene as a Trigger in Biomedicine: Molecular Design and Spontaneous Assembly. Advanced Materials 2021, 33 (26) , 2007290. https://doi.org/10.1002/adma.202007290
    25. Fabio Rizzo, Nermin Seda Kehr. Recent Advances in Injectable Hydrogels for Controlled and Local Drug Delivery. Advanced Healthcare Materials 2021, 10 (1) https://doi.org/10.1002/adhm.202001341
    26. Yueshan Li, Yulin Zhang, Ji Lan, Bin Yan, Junying Qiu, Qingdang Meng, Yinjie Peng, Lingying Shi, Rong Ran. Ion-conducting gel with light-controlled variable conductivity: From cyclodextrin to messenger of light. Polymer 2020, 203 , 122798. https://doi.org/10.1016/j.polymer.2020.122798
    27. Senne Seneca, Sumit Kumar Pramanik, Lien D’Olieslaeger, Gunter Reekmans, Dirk Vanderzande, Peter Adriaensens, Anitha Ethirajan. Nanocapsules with stimuli-responsive moieties for controlled release employing light and enzymatic triggers. Materials Chemistry Frontiers 2020, 4 (7) , 2103-2112. https://doi.org/10.1039/D0QM00244E
    28. Weiyi Zhao, Yang Li, Xiang Zhang, Rui Zhang, Yang Hu, Cyrille Boyer, Fu-Jian Xu. Photo-responsive supramolecular hyaluronic acid hydrogels for accelerated wound healing. Journal of Controlled Release 2020, 323 , 24-35. https://doi.org/10.1016/j.jconrel.2020.04.014
    29. Rui Zhang, Hengzhi Ruan, Qionglong Fu, Xuedong Zhu, Yuan Yao. A high strain, adhesive, self-healable poly(acrylic acid) hydrogel with temperature sensitivity as an epidermal sensor. Materials Advances 2020, 1 (3) , 329-333. https://doi.org/10.1039/D0MA00282H
    30. Tingting Yu, Hufei Wang, Yunfan Zhang, Xing Wang, Bing Han. The Delivery of RNA-Interference Therapies Based on Engineered Hydrogels for Bone Tissue Regeneration. Frontiers in Bioengineering and Biotechnology 2020, 8 https://doi.org/10.3389/fbioe.2020.00445
    31. Mosa Alsehli. Polymeric nanocarriers as stimuli-responsive systems for targeted tumor (cancer) therapy: Recent advances in drug delivery. Saudi Pharmaceutical Journal 2020, 28 (3) , 255-265. https://doi.org/10.1016/j.jsps.2020.01.004
    32. Weipeng Wei, Hongfang Li, Chengchen Yin, Fushan Tang. Research progress in the application of in situ hydrogel system in tumor treatment. Drug Delivery 2020, 27 (1) , 460-468. https://doi.org/10.1080/10717544.2020.1739171
    33. Dilshad Qureshi, Suraj Kumar Nayak, Samarendra Maji, Arfat Anis, Doman Kim, Kunal Pal. Environment sensitive hydrogels for drug delivery applications. European Polymer Journal 2019, 120 , 109220. https://doi.org/10.1016/j.eurpolymj.2019.109220
    34. Limin Chen, Dan Yang, Jie Feng, Min Zhang, Qiuping Qian, Yunlong Zhou. Switchable modulation of bacterial growth and biofilm formation based on supramolecular tripeptide amphiphiles. Journal of Materials Chemistry B 2019, 7 (41) , 6420-6427. https://doi.org/10.1039/C9TB00973F
    35. Limin Chen, Jie Feng, Dan Yang, Falin Tian, Xiaomin Ye, Qiuping Qian, Shuai Wei, Yunlong Zhou. Sequence isomerism-dependent self-assembly of glycopeptide mimetics with switchable antibiofilm properties. Chemical Science 2019, 10 (35) , 8171-8178. https://doi.org/10.1039/C9SC00193J
    36. Lin Dai, Jinshun Lu, Fangong Kong, Kefeng Liu, Huige Wei, Chuanling Si. Reversible photo-controlled release of bovine serum albumin by azobenzene-containing cellulose nanofibrils-based hydrogel. Advanced Composites and Hybrid Materials 2019, 2 (3) , 462-470. https://doi.org/10.1007/s42114-019-00112-9
    37. Andy Hernández Montoto, Antoni Llopis‐Lorente, Mónica Gorbe, José M. Terrés, Roberto Cao‐Milán, Borja Díaz de Greñu, María Alfonso, Javier Ibañez, María D. Marcos, Mar Orzáez, Reynaldo Villalonga, Ramón Martínez‐Máñez, Félix Sancenón. Janus Gold Nanostars–Mesoporous Silica Nanoparticles for NIR‐Light‐Triggered Drug Delivery. Chemistry – A European Journal 2019, 25 (36) , 8471-8478. https://doi.org/10.1002/chem.201900750
    38. Coro Echeverria, Susete Fernandes, Maria Godinho, João Borges, Paula Soares. Functional Stimuli-Responsive Gels: Hydrogels and Microgels. Gels 2018, 4 (2) , 54. https://doi.org/10.3390/gels4020054
    39. Samarendra Maji, Valentin V. Jerca, Florica A. Jerca, Richard Hoogenboom. Smart polymeric gels. 2018, 179-230. https://doi.org/10.1016/B978-0-08-102179-8.00007-7
    40. Pu Xiao, Jing Zhang, Jiacheng Zhao, Martina H. Stenzel. Light-induced release of molecules from polymers. Progress in Polymer Science 2017, 74 , 1-33. https://doi.org/10.1016/j.progpolymsci.2017.06.002
    Download PDF

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect