Immobilization of Metal-Organic Framework Copper(II) Benzene-1,3,5-tricarboxylate (CuBTC) onto Cotton Fabric as a Nitric Oxide Release Catalyst

ACS Applied Materials and Interfaces

Volumn 7, Issue 48, 2015, Pages 26742-26750

  Neufeld, Megan J ^a   Harding, Jacqueline L ^b   Reynolds, Melissa M ^a,c  

^a Veterinary Dentistry and Oral Surgery   (United States)

^b Department of Metallurgical and Materials Engineering   (United States)

^c Department of Mechanical Engineering   (United States)

Author keywords

catalysis; cotton; hard soft interfaces; metal organic frameworks; nitric oxide

Indexed keywords

BENZENE; BENZENE REFINING; CATALYSIS; CATALYSTS; CHARACTERIZATION; COPPER; COTTON FABRICS; CRYSTALLINE MATERIALS; DEPOSITION; FUNCTIONAL MATERIALS; FUNCTIONAL POLYMERS; NITRIC OXIDE; ORGANIC POLYMERS; ORGANOMETALLICS; POLYMERS; SUBSTRATES;

CARBOXYL-FUNCTIONALIZED; FLEXIBLE POLYMERIC SUBSTRATES; HETEROGENEOUS CATALYST; METAL ORGANIC FRAMEWORK; METALORGANIC FRAMEWORKS (MOFS); NITRIC OXIDE RELEASE; SECONDARY SUPPORTS; SOFT INTERFACES;

COTTON;

COPPER; NITRIC OXIDE; TRICARBOXYLIC ACID; TRIMESIC ACID;

CATALYSIS; CHEMISTRY; COTTON; METHYLATION; SPECTROSCOPY; X RAY DIFFRACTION;

CATALYSIS; COPPER; COTTON FIBER; METHYLATION; NITRIC OXIDE; SPECTRUM ANALYSIS; TRICARBOXYLIC ACIDS; X-RAY DIFFRACTION;

EID: 84949595593     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/acsami.5b08773     Document Type: Article

References (61)

1. Zhu, H.; Ka, B.; Murad, F. Nitric Oxide Accelerates the Recovery from Burn Wounds World J. Surg. 2007, 31 (4) 624-631 10.1007/s00268-007-0727-3
2. Wu, Y.; Zhou, Z.; Meyerhoff, M. E. In vitro Platelet Adhesion on Polymeric Surfaces with Varying Fluxes of Continuous Nitric Oxide Release J. Biomed. Mater. Res., Part A 2007, 81 (4) 956-963 10.1002/jbm.a.31105
3. Gross, S. S.; Wolin, M. S. NITRIC-OXIDE-PATHOPHYSIOLOGICAL MECHANISMS Annu. Rev. Physiol. 1995, 57, 737-769 10.1146/annurev.ph.57.030195.003513
4. Marletta, M. A. NITRIC-OXIDE-BIOSYNTHESIS AND BIOLOGICAL SIGNIFICANCE Trends Biochem. Sci. 1989, 14 (12) 488-492 10.1016/0968-0004(89)90181-3
5. Witte, M. B.; Barbul, A. Role of Nitric Oxide in Wound Repair Am. J. Surg. 2002, 183 (4) 406-412 10.1016/S0002-9610(02)00815-2
6. Bogdan, C. Nitric Oxide and the Immune Response Nat. Immunol. 2001, 2 (10) 907-916 10.1038/ni1001-907
7. Al-Sa'doni, H. H.; Ferro, A. S-Nitrosothiols as Nitric Oxide-Donors: Chemistry, Biology and Possible Future Therapeutic Applications Curr. Med. Chem. 2004, 11 (20) 2679-2690 10.2174/0929867043364397
8. Reynolds, M. M.; Hrabie, J. A.; Oh, B. K.; Politis, J. K.; Citro, M. L.; Keefer, L. K.; Meyerhoff, M. E. Nitric Oxide Releasing Polyurethanes with Covalently Linked Diazeniumdiolated Secondary Amine Biomacromolecules 2006, 7 (3) 987-994 10.1021/bm060028o
9. Seabra, A. B.; Duran, N. Nitric Oxide-Releasing Vehicles for Biomedical Applications J. Mater. Chem. 2010, 20 (9) 1624-1637 10.1039/B912493B
10. Jen, M. C.; Serrano, M. C.; van Lith, R.; Ameer, G. A. Polymer-Based Nitric Oxide Therapies: Recent Insights for Biomedical Applications Adv. Funct. Mater. 2012, 22 (2) 239-260 10.1002/adfm.201101707
11. McKinlay, A. C.; Morris, R. E.; Horcajada, P.; Ferey, G.; Gref, R.; Couvreur, P.; Serre, C. BioMOFs: Metal-Organic Frameworks for Biological and Medical Applications Angew. Chem., Int. Ed. 2010, 49 (36) 6260-6266 10.1002/anie.201000048
12. Carpenter, A. W.; Schoenfisch, M. H. Nitric Oxide Release: Part II. Therapeutic Applications Chem. Soc. Rev. 2012, 41 (10) 3742-3752 10.1039/c2cs15273h
13. McKinlay, A. C.; Allan, P.; Renouf, C. L.; Duncan, M. J.; Wheatley, P. S.; Warrender, S. J.; Dawson, D. M.; Ashbrook, S. E. M.; Gil, B.; Marszalek, B.; Duren, T.; Williams, J. J.; Charrier, C.; Mercer, D. K.; Teat, S. J.; Morris, R. E. Multirate Delivery of Multiple Therapeutic Agents from Metal-Organic Frameworks APL Mater. 2014, 2, 124108-124115 10.1063/1.4903290
14. Horcajada, P.; Chalati, T.; Serre, C.; Gillet, B.; Sebrie, C.; Baati, T.; Eubank, J. F.; Heurtaux, D.; Clayette, P.; Kreuz, C.; Chang, J.-S.; Hwang, Y. K.; Marsaud, V.; Bories, P.-N.; Cynober, L.; Gil, S.; Ferey, G.; Couvreur, P.; Gref, R. Porous Metal-Organic-Framework Nanoscale Carriers as a Potential Platform for Drug Delivery and Imaging Nat. Mater. 2010, 9 (2) 172-178 10.1038/nmat2608
15. Horcajada, P.; Gref, R.; Baati, T.; Allan, P. K.; Maurin, G.; Couvreur, P.; Ferey, G.; Morris, R. E.; Serre, C. Metal-Organic Frameworks in Biomedicine Chem. Rev. 2012, 112 (2) 1232-1268 10.1021/cr200256v
16. Harding, J. L.; Reynolds, M. M. Metal Organic Frameworks as Nitric Oxide Catalysts J. Am. Chem. Soc. 2012, 134 (7) 3330-3333 10.1021/ja210771m
17. Harding, J. L.; Reynolds, M. M. Composite Materials with Embedded Metal Organic Framework Catalysts for Nitric Oxide Release from Bioavailable S-Nitrosothiols J. Mater. Chem. B 2014, 2 (17) 2530-2536 10.1039/C3TB21458C
18. Davies, K. M.; Wink, D. A.; Saavedra, J. E.; Keefer, L. K. Chemistry of the Diazeniumdiolates. 2. Kinetics and Mechanism of Dissociation to Nitric Oxide in Aqueous Solution J. Am. Chem. Soc. 2001, 123 (23) 5473-5481 10.1021/ja002899q
19. Singh, R. J.; Hogg, N.; Joseph, J.; Kalyanaraman, B. Mechanism of Nitric Oxide Release from S-Nitrosothiols J. Biol. Chem. 1996, 271 (31) 18596-18603 10.1074/jbc.271.31.18596
20. Zhang, Y.; Hogg, N. S-Nitrosothiols: Cellular Formation and Transport Free Radical Biol. Med. 2005, 38 (7) 831-838 10.1016/j.freeradbiomed.2004.12.016
21. Giustarini, D.; Milzani, A.; Colombo, R.; Dalle-Donne, I.; Rossi, R. Nitric oxide and S-nitrosothiols in Human Blood Clin. Chim. Acta 2003, 330 (1-2) 85-98 10.1016/S0009-8981(03)00046-9
22. Dicks, A. P.; Swift, H. R.; Williams, D. L. H.; Butler, A. R.; AlSadoni, H. H.; Cox, B. G. Identification of Cu+ as the Effective Reagent in Nitric Oxide Formation from S-Nitrosothiols (RSNO) J. Chem. Soc., Perkin Trans. 2 1996, 4) 481-487 10.1039/p29960000481
23. Bradshaw, D.; Garai, A.; Huo, J. Metal-Organic Framework Growth at Functional Interfaces: Thin Films and Composites for Diverse Applications Chem. Soc. Rev. 2012, 41 (6) 2344-2381 10.1039/C1CS15276A
24. Shekhah, O.; Liu, J.; Fischer, R. A.; Woll, C. MOF Thin Films: Existing and Future Applications Chem. Soc. Rev. 2011, 40 (2) 1081-1106 10.1039/c0cs00147c
25. Kreno, L. E.; Leong, K.; Farha, O. K.; Allendorf, M.; Van Duyne, R. P.; Hupp, J. T. Metal-Organic Framework Materials as Chemical Sensors Chem. Rev. 2012, 112 (2) 1105-1125 10.1021/cr200324t
26. Li, J.-R.; Sculley, J.; Zhou, H.-C. Metal-Organic Frameworks for Separations Chem. Rev. 2012, 112 (2) 869-932 10.1021/cr200190s
27. Yu, Y.; Ren, Y.; Shen, W.; Deng, H.; Gao, Z. Applications of Metal-Organic Frameworks as Stationary Phases in Chromatography TrAC, Trends Anal. Chem. 2013, 50, 33-41 10.1016/j.trac.2013.04.014
28. Furukawa, H.; Cordova, K. E.; O'Keeffe, M.; Yaghi, O. M. The Chemistry and Applications of Metal-Organic Frameworks Science 2013, 341 (6149) 974 10.1126/science.1230444
29. Hinterholzinger, F.; Scherb, C.; Ahnfeldt, T.; Stock, N.; Bein, T. Oriented Growth of the Functionalized Metal-Organic Framework CAU-1 on -OH- and -COOH-Terminated Self-Assembled Monolayers Phys. Chem. Chem. Phys. 2010, 12 (17) 4515-4520 10.1039/b924657f
30. Liu, B.; Tu, M.; Zacher, D.; Fischer, R. A. Multi Variant Surface Mounted Metal-Organic Frameworks Adv. Funct. Mater. 2013, 23 (30) 3790-3798 10.1002/adfm.201202996
31. Zhuang, J.L.; Terfort, A.; Woll, C. Formation of Oriented and Patterned Films of Metal-Organic Frameworks by Liquid Phase Epitaxy: A Review Coord. Chem. Rev. 2015, in press 10.1016/j.ccr.2015.09.013
32. Schoedel, A.; Scherb, C.; Bein, T. Oriented Nanoscale Films of Metal-Organic Frameworks by Room-Temperature Gel-Layer Synthesis Angew. Chem., Int. Ed. 2010, 49 (40) 7225-7228 10.1002/anie.201001684
33. Zhuang, J. L.; Ar, D.; Yu, X. J.; Liu, J. X.; Terfort, A. Patterned Deposition of Metal-Organic Frameworks onto Plastic, Paper, and Textile Substrates by Inkjet Printing of a Precursor Solution Adv. Mater. 2013, 25 (33) 4631-4635 10.1002/adma.201301626
34. Tsotsalas, M.; Liu, J. X.; Tettmann, B.; Grosjean, S.; Shahnas, A.; Wang, Z. B.; Azucena, C.; Addicoat, M.; Heine, T.; Lahann, J.; Overhage, J.; Brase, S.; Gliemann, H.; Woll, C. Fabrication of Highly Uniform Gel Coatings by the Conversion of Surface-Anchored Metal-Organic Frameworks J. Am. Chem. Soc. 2014, 136 (1) 8-11 10.1021/ja409205s
35. Arslan, H. K.; Shekhah, O.; Wohlgemuth, J.; Franzreb, M.; Fischer, R. A.; Woll, C. High-Throughput Fabrication of Uniform and Homogenous MOF Coatings Adv. Funct. Mater. 2011, 21 (22) 4228-4231 10.1002/adfm.201101592
36. Gascon, J.; Aguado, S.; Kapteijn, F. Manufacture of Dense Coatings of Cu-3(BTC)(2) (HKUST-1) on Alpha-Alumina Microporous Mesoporous Mater. 2008, 113 (1-3) 132-138 10.1016/j.micromeso.2007.11.014
37. Tu, M.; Wannapaiboon, S.; Fischer, R. A. Programmed Functionalization of SURMOFs via Liquid Phase Heteroepitaxial Growth and Post-Synthetic Modification Dalton Trans. 2013, 42 (45) 16029-16035 10.1039/c3dt51457a
38. Munch, A. S.; Lohse, M. S.; Hausdorf, S.; Schreiber, G.; Zacher, D.; Fischer, R. A.; Mertens, F. Room Temperature Preparation Method for Thin MOF-5 Films on Metal and Fused Silica Surfaces using the controlled SBU Approach Microporous Mesoporous Mater. 2012, 159, 132-138 10.1016/j.micromeso.2012.04.023
39. Nan, J. P.; Dong, X. L.; Wang, W. J.; Jin, W. Q.; Xu, N. P. Step-by-Step Seeding Procedure for Preparing HKUST-1 Membrane on Porous alpha-Alumina Support Langmuir 2011, 27 (8) 4309-4312 10.1021/la200103w
40. Hinterholzinger, F. M.; Wuttke, S.; Roy, P.; Preusse, T.; Schaate, A.; Behrens, P.; Godt, A.; Bein, T. Highly Oriented Surface-Growth and Covalent Dye Labeling of Mesoporous Metal-Organic Frameworks Dalton Trans 2012, 41 (14) 3899-3901 10.1039/c2dt12265k
41. Hermes, S.; Schroder, F.; Chelmowski, R.; Woll, C.; Fischer, R. A. Selective Nucleation and Growth of Metal-Organic Open Framework Thin Films on Patterned COOH/CF3-Terminated Self-Assembled Monolayers on Au(111) J. Am. Chem. Soc. 2005, 127 (40) 13744-13745 10.1021/ja053523l
42. Makiura, R.; Motoyama, S.; Umemura, Y.; Yamanaka, H.; Sakata, O.; Kitagawa, H. Surface Nano-Architecture of a Metal-Organic Framework Nat. Mater. 2010, 9, 565-571 10.1038/nmat2769
43. Nijem, N.; Fuersich, K.; Kelly, S. T.; Swain, C.; Leone, S. R.; Gilles, M. K.; Gilles; Fürsich, K. HKUST-1 Thin Film Layer-by-Layer Liquid Phase Epitaxial Growth: Film Properties and Stability Dependence on Layer Number Cryst. Growth Des. 2015, 15 (6) 2948-2957 10.1021/acs.cgd.5b00384
44. Zhuang, J.-L.; Kind, M.; Grytz, C. M.; Farr, F.; Diefenbach, M.; Tussupbayev, S.; Holthausen, M. C.; Terfort, A. Insight into the Oriented Growth of Surface-Attached Metal-Organic Frameworks: Surface Functionality, Deposition Temperature, and First Layer Order J. Am. Chem. Soc. 2015, 137 (25) 8237-8243 10.1021/jacs.5b03948
45. Kusgens, P.; Siegle, S.; Kaskel, S. Crystal Growth of the Metal-Organic Framework Cu-3(BTC)(2) on the Surface of Pulp Fibers Adv. Eng. Mater. 2009, 11 (1-2) 93-95 10.1002/adem.200800274
46. Pinto, M. D.; Sierra-Avila, C. A.; Hinestroza, J. P. In situ synthesis of a Cu-BTC Metal-Organic Framework (MOF 199) onto Cellulosic Fibrous Substrates: Cotton Cellulose 2012, 19 (5) 1771-1779 10.1007/s10570-012-9752-y
47. Centrone, A.; Yang, Y.; Speakman, S.; Bromberg, L.; Rutledge, G. C.; Hatton, T. A. Growth of Metal-Organic Frameworks on Polymer Surfaces J. Am. Chem. Soc. 2010, 132 (44) 15687-15691 10.1021/ja106381
48. O'Neill, L. D.; Zhang, H. F.; Bradshaw, D. Macro-/Microporous MOF Composite Beads J. Mater. Chem. 2010, 20 (27) 5720-5726 10.1039/c0jm00515k
49. Meilikhov, M.; Yusenko, K.; Schollmeyer, E.; Mayer, C.; Buschmann, H. J.; Fischer, R. A. Stepwise Deposition of Metal Organic Frameworks on Flexible Synthetic Polymer Surfaces Dalton Trans. 2011, 40 (18) 4838-4841 10.1039/c0dt01820a
50. Rodriguez, H. S.; Hinestroza, J. P.; Ochoa-Puentes, C.; Sierra, C. A.; Soto, C. Y. Antibacterial Activity against Escherichia Coli of Cu-BTC (MOF-199) Metal-Organic Framework Immobilized onto Cellulosic Fibers J. Appl. Polym. Sci. 2014, 131 (19) 40815 10.1002/app.40815
51. Cacho-Bailo, F.; Catalan-Aguirre, S.; Etxeberria-Benavides, M.; Karvan, O.; Sebastian, V.; Tellez, C.; Coronas, J. Metal-Organic Framework Membranes on the Inner-Side of a Polymeric Hollow Fiber by Microfluidic Synthesis J. Membr. Sci. 2015, 476, 277-285 10.1016/j.memsci.2014.11.016
52. Abbasi, A. R.; Akhbari, K.; Morsali, A. Dense Coating of Surface Mounted CuBTC Metal-Organic Framework Nanostructures on Silk Fibers, Prepared by Layer-by-Layer Method under Ultrasound Irradiation with Antibacterial Activity Ultrason. Sonochem. 2012, 19 (4) 846-852 10.1016/j.ultsonch.2011.11.016
53. Jia, B.; Mei, Y.; Cheng, L.; Zhou, J.; Zhang, L. Preparation of Copper Nanoparticles Coated Cellulose Films with Antibacterial Properties through One-Step Reduction ACS Appl. Mater. Interfaces 2012, 4, 2897-2902 10.1021/am3007609
54. Zhukovskyi, M.; Sanchez-Botero, L.; McDonald, M. P.; Hinestroza, J.; Kuno, M. Nanowire-Functionalized Cotton Textiles ACS Appl. Mater. Interfaces 2014, 6 (4) 2262-2269 10.1021/am4052602
55. Wang, Z.; Wang, J.; Li, M.; Sun, K.; Liu, C. Three-Dimensional Printed Acrylonitrile Butadiene Styrene Framework Coated with Cu-BTC Metal-Organic Frameworks for Removal of Methylene Blue Sci. Rep. 2014, 4, 1-7 10.1038/srep05939
56. Mao, Y.; Shi, L.; Huang, H.; Cao, W.; Li, J.; Sun, L.; Jin, X.; Peng Room Temperature Synthesis of Free-Standing HKUST-1 Membranes from Copper Hydroxide Nanostrands for Gas Separation Chem. Commun. 2013, 49, 5666-5668 10.1039/c3cc42601g
57. Harding, J. L.; Metz, J. M.; Reynolds, M. M. A Tunable, Stable, and Bioactive MOF Catalyst for Generating a Localized Therapeutic from Endogenous Sources Adv. Funct. Mater. 2014, 24 (47) 7503-7509 10.1002/adfm.201402529
58. Coneski, P. N.; Schoenfisch, M. H. Nitric Oxide Release: Part III. Measurement and Reporting Chem. Soc. Rev. 2012, 41 (10) 3753-3758 10.1039/c2cs15271a
59. Gao, W.-Y.; Cai, R.; Pham, T.; Forrest, K. A.; Hogan, A.; Nugent, P.; Williams, K.; Wojtas, L.; Luebke, R.; Weselinski, L. J.; Zaworotko, M. J.; Space, B.; Chen, Y.-S.; Eddaoudi, M.; Shi, X.; Ma, S. Remote Stabilization of Copper Paddlewheel Based Molecular Building Blocks in Metal-Organic Frameworks Chem. Mater. 2015, 27 (6) 2144-2151 10.1021/acs.chemmater.5b00084
60. Timerghazin, K. Q.; Peslherbe, H. G.; English, M. A. Resonance Description of S-Nitrosothiols: Insights into Reactivity Org. Lett. 2007, 9, 3049-3052 10.1021/ol0711016
61. Melzer, M. M.; Mossin, S.; Cardenas, A. J. P.; Williams, K. D.; Zhang, S.; Meyer, K.; Warren, T. H. A Copper(II) Thiolate from Reductive Cleavage of an S-Nitrosothiol Inorg. Chem. 2012, 51, 8658-8660 10.1021/ic301356h