一氧化碳释放材料的研究进展
Progress in Research of Carbon Monoxide Releasing Materials
DOI: 10.12677/MS.2021.115077, PDF,    国家自然科学基金支持
作者: 李伟杰, 牟羿贤, 胥 聪, 杨鑫磊, 翁亚军*:西南交通大学材料科学与工程学院,四川 成都
关键词: 一氧化碳释放分子大分子与纳米材料荧光探针Carbon Monoxide Releasing Molecules Macromolecules and Nanomaterials Fluorescent Probes
摘要: 一氧化碳(Carbon monoxide, CO)是一种具有重要生理功能的内源性气体信号分子,在治疗多种疾病方面显示出较大的应用前景,然而CO的固载和体内释放方式不理想限制了其临床应用。设计和制备具有靶向控释的一氧化碳释放材料成为了该方向的研究热点。本文综述了近年来报道的CO释放材料的种类、释放触发机制及释放检测等,并比较了其生物相容性、CO释放时长等方面的性能,展望了未来CO释放型材料的发展趋势。
Abstract: Carbon monoxide (CO) was an endogenous gas signaling molecule with important physiological functions and had shown great potential in the treatment of various diseases. However, the clinical applications were limited by the unsatisfactory way of CO sequestration and in vivo releasing. The design and preparation of CO release materials with targeted controlled release had become a top research priority in this direction. In this paper, we reviewed the types of CO-releasing materials, release trigger mechanisms and release detection reported in recent years. We compared their performance in terms of biocompatibility, CO release duration, etc., and looked forward to the future development trend of CO-releasing materials.
文章引用:李伟杰, 牟羿贤, 胥聪, 杨鑫磊, 翁亚军. 一氧化碳释放材料的研究进展[J]. 材料科学, 2021, 11(5): 665-674. https://doi.org/10.12677/MS.2021.115077

参考文献

[1] Adach, W. and Olas, B. (2019) Carbon Monoxide and Its Donors—Their Implications for Medicine. Future Medicinal Chemistry, 11, 60-73. [Google Scholar] [CrossRef] [PubMed]
[2] Motterlini, R., Clark, J.E., Foresti, R., Sara-thchandra, P., Mann, B.E. and Green, C.J. (2002) Carbon Monoxide-Releasing Molecules: Characterization of Bio-chemical and Vascular Activities. Circulation Research, 90, e17-e24. [Google Scholar] [CrossRef] [PubMed]
[3] Clark, J.E., Naughton, P., Shurey, S., Green, C.J., Johnson, T.R., Mann, B.E., et al. (2003) Cardioprotective Actions by a Water-Soluble Carbon Monoxide-Releasing Molecule. Circu-lation Research, 93, e2-e8. [Google Scholar] [CrossRef
[4] Ling, K., Men, F., Wang, W.C., Zhou, Y.Q., Zhang, H.W. and Ye, D.W. (2018) Carbon Monoxide and Its Controlled Release: Therapeutic Application, Detection, and Development of Carbon Monoxide Releasing Molecules (CORMs). Journal of Medicinal Chemistry, 61, 2611-2635. [Google Scholar] [CrossRef] [PubMed]
[5] Winburn, I.C., Gunatunga, K., McKernan, R.D., Walker, R.J., Sammut, I.A. and Harrison, J.C. (2012) Cell Damage Following Carbon Monoxide Releasing Molecule Exposure: Implications for Therapeutic Applications. Basic & Clinical Pharmacology & Toxicology, 111, 31-41. [Google Scholar] [CrossRef] [PubMed]
[6] Romão, C.C., Blättler, W.A., Seixas, J.D. and Bernardes, G.J.L. (2012) Developing Drug Molecules for Therapy with Carbon Monoxide. Chemical Society Reviews, 41, 3571-3583. [Google Scholar] [CrossRef
[7] Ji, X.Y., Damera, K., Zheng, Y.Q., Yu, B., Otterbein, L.E. and Wang, B. (2016) Toward Carbon Monoxide-Based Therapeutics: Critical Drug Delivery and Developability Issues. Journal of Pharmaceutical Sciences, 105, 406-416. [Google Scholar] [CrossRef] [PubMed]
[8] Pitchumony, T.S., Spingler, B., Motterlini, R. and Alberto, R. (2010) Syntheses, Structural Characterization and CO Releasing Properties of Boranocarbonate [H3BCO2H]- Derivatives. Organic & Biomolecular Chemistry, 8, 4849-4854. [Google Scholar] [CrossRef
[9] Zelzer, M., Todd, S.J., Hirst, A.R., McDonald, T.O. and Ulijn, R.V. (2013) Enzyme Responsive Materials: Design Strategies and Future Developments. Biomaterials Science, 1, 11-39. [Google Scholar] [CrossRef
[10] Wang, D.Z., Viennois, E., Ji, K., Damera, K., Draganov, A., Zheng, Y., et al. (2014) A Click-and-Release Approach to CO Prodrugs. Chemical Communications, 50, 15890-15893. [Google Scholar] [CrossRef
[11] Bruckmann, N.E., Wahl, M., Reiss, G.J., Kohns, M., Wätjen, W. and Kunz, P.C. (2011) Polymer Conjugates of Photoinducible CO-Releasing Molecules. European Journal of Inorganic Chemistry, 2011, 4571-4577. [Google Scholar] [CrossRef
[12] Govender, P., Pai, S., Schatzschneider, U. and Smith, G.S. (2013) Next Generation PhotoCORMs: Polynuclear Tricarbonylmanganese(I)- Functionalized Polypyridyl Metallodendrimers. Inorganic Chemistry, 52, 5470-5478. [Google Scholar] [CrossRef] [PubMed]
[13] Razavet, M., Artero, V., Cavazza, C., Oudart, Y., Lebrun, C., Fontecil-la-Camps, J.C., et al. (2007) Tricarbonyl Manganese(I)-Lysozyme Complex: A Structurally Characterized Organometallic Protein. Chemical Communications, 27, 2805-2807. [Google Scholar] [CrossRef
[14] Seixas, J.D., Mukhopadhyay, A., Santos-Silva, T., Otterbein, L.E., Gallo, D.J., Rodrigues, S.S., et al. (2013) Characterization of a Versatile Organometallic Pro-Drug (CORM) for Experimental CO Based Therapeutics. Dalton Transactions, 42, 5985-5998. [Google Scholar] [CrossRef
[15] Tabe, H., Fujita, K., Abe, S., Tsujimoto, M., Kuchimaru, T., Kizaka-Kondoh, S., et al. (2015) Preparation of a Cross-Linked Porous Protein Crystal Containing Ru Carbonyl Complexes as a CO-Releasing Extracellular Scaffold. Inorganic Chemistry, 54, 215-220. [Google Scholar] [CrossRef] [PubMed]
[16] Nagao, S., Taguchi, K., Sakai, H., Yamasaki, K., Watanabe, H., Otagiri, M., et al. (2016) Carbon Monoxide-Bound Hemoglobin Vesicles Ameliorate Multiorgan Injuries Induced by Severe Acute Pancreatitis in Mice by Their Anti-Inflammatory and Antioxidant Properties. International Journal of Nanomedicine, 11, 5611-5620. [Google Scholar] [CrossRef
[17] Raptopoulou, C.P. (2021) Metal-Organic Frameworks: Synthetic Methods and Potential Applications. Materials, 14, Article No. 310. [Google Scholar] [CrossRef] [PubMed]
[18] Carmona, F.J., Maldonado, C.R., Ikemura, S., Romão, C.C., Huang, Z., Xu, H., et al. (2018) Coordination Modulation Method to Prepare New Metal-Organic Framework-Based CO-Releasing Materials. ACS Applied Materials & Interfaces, 10, 31158-31167. [Google Scholar] [CrossRef] [PubMed]
[19] Diring, S., Carne-Sanchez, A., Zhang, J.C., Ikemura, S., Kim, C., Inaba, H., et al. (2017) Light Responsive Metal-Organic Frameworks as Controllable CO-Releasing Cell Culture Sub-strates. Chemical Science, 8, 2381-2386. [Google Scholar] [CrossRef
[20] Prockop, L.D. and Chichkova, R.I. (2007) Carbon Monoxide Intoxi-cation: An Updated Review. Journal of the Neurological Sciences, 262, 122-130. [Google Scholar] [CrossRef] [PubMed]
[21] Yao, J., Liu, Y., Wang, J., Jiang, Q., She, D., Guo, H., et al. (2019) On-Demand CO Release for Amplification of Chemotherapy by MOF Functionalized Magnetic Carbon Nanoparticles with NIR Irradiation. Biomaterials, 195, 51-62. [Google Scholar] [CrossRef] [PubMed]
[22] Li, W.P., Su, C.H., Tsao, L.C., Chang, C.T., Hsu, Y.P. and Yeh, C.S. (2016) Controllable CO Release Following Near Infrared Light-Induced Cleavage of Iron Carbonyl Derivatized Prussian Blue Nanoparticles for CO-Assisted Synergistic Treatment. ACS Nano, 10, 11027-11036. [Google Scholar] [CrossRef] [PubMed]
[23] Ma, M., Noei, H., Mienert, B., Niesel, J., Bill, E., Muhler, M., et al. (2013) Iron Metal-Organic Frameworks MIL-88B and NH2-MIL-88B for the Loading and Delivery of the Gas-otransmitter Carbon Monoxide. Chemistry—A European Journal, 19, 6785-6790. [Google Scholar] [CrossRef] [PubMed]
[24] Hasegawa, U., van der Vlies, A.J., Simeoni, E., Wandrey, C. and Hubbell, J.A. (2010) Carbon Monoxide-Releasing Micelles for Immunotherapy. Journal of the American Chemical Society, 132, 18273-18280. [Google Scholar] [CrossRef] [PubMed]
[25] Yin, H., Fang, J., Liao, L., Nakamura, H. and Maeda, H. (2014) Sty-rene-Maleic Acid Copolymer-Encapsulated CORM2, a Water-Soluble Carbon Monoxide (CO) Donor with a Constant CO-Releasing Property, Exhibits Therapeutic Potential for Inflammatory Bowel Disease. Journal of Controlled Release, 187, 14-21. [Google Scholar] [CrossRef] [PubMed]
[26] Matson, J.B., Webber, M.J., Tamboli, V.K., Weber, B. and Stupp, S.I. (2012) A peptide-based material for therapeutic carbon monoxide delivery. Soft Matter, 8, 6689-6692. [Google Scholar] [CrossRef
[27] Pai, S., Radacki, K. and Schatzschneider, U. (2014) Sonogashira, CuAAC, and Oxime Ligations for the Synthesis of MnI Tricarbonyl PhotoCORM Peptide Conjugates. European Journal of Inorganic Chemistry, 18, 2886-2895. [Google Scholar] [CrossRef
[28] Qureshi, O.S., Zeb, A., Akram, M., Kim, M.-S., Kang, J.-H., Kim, H.-S., et al. (2016) Enhanced Acute Anti-Inflammatory Effects of CORM-2-Loaded Nanoparticles via Sustained Carbon Monoxide Delivery. European Journal of Pharmaceutics and Biopharmaceutics, 108, 187-195. [Google Scholar] [CrossRef] [PubMed]
[29] Carmona, F.J., Jiménez-Amezcua, I., Rojas, S., Romão, C.C., Navarro, J.A.R., Maldonado, C.R., et al. (2017) Aluminum Doped MCM-41 Nanoparticles as Platforms for the Dual Encapsulation of a CO-Releasing Molecule and Cisplatin. Inorganic Chemistry, 56, 10474-10480. [Google Scholar] [CrossRef] [PubMed]
[30] Dördelmann, G., Pfeiffer, H., Birkner, A. and Schatzschneider, U. (2011) Silicium Dioxide Nanoparticles as Carriers for Photoactivatable CO-Releasing Molecules (PhotoCORMs). Inorganic Chemistry, 50, 4362-4367. [Google Scholar] [CrossRef] [PubMed]
[31] Nguyen, D., Adnan, N.N.M., Oliver, S. and Boyer, C. (2016) The Inter-action of CORM-2 with Block Copolymers Containing Poly (4-vinylpyridine): Macromolecular Scaffolds for Carbon Monoxide Delivery in Biological Systems. Macromolecular Rapid Communications, 37, 739-744. [Google Scholar] [CrossRef] [PubMed]
[32] Mukhopadhyay, S., Sarkar, A., Chattopadhyay, P. and Dhara, K. (2020) Recent Advances in Fluorescence Light-Up Endogenous and Exogenous Carbon Monoxide Detection in Biology. Chemistry—An Asian Journal, 15, 3162-3179. [Google Scholar] [CrossRef] [PubMed]
[33] Davidge, K.S., Sanguinetti, G., Yee, C.H., Cox, A.G., McLeod, C.W., Monk, C.E., et al. (2009) Carbon Monoxide-Releasing Antibacterial Molecules Target Respiration and Global Transcriptional Regulators. Journal of Biological Chemistry, 284, 4516-4524. [Google Scholar] [CrossRef
[34] McLean, S., Mann, B.E. and Poole, R.K. (2012) Sulfite Species En-hance Carbon Monoxide Release from CO-Releasing Molecules: Implications for the Deoxymyoglobin Assay of Activity. Analytical Biochemistry, 427, 36-40. [Google Scholar] [CrossRef] [PubMed]
[35] Atkin, A.J., Lynam, J.M., Moulton, B.E., Sawle, P., Motterlini, R., Boyle, N.M., et al. (2011) Modification of The Deoxy-Myoglobin/Carbonmonoxy-Myoglobin UV-Vis Assay for Re-liable Determination of CO-Release Rates from Organometallic Carbonyl Complexes. Dalton Transactions, 40, 5755-5761. [Google Scholar] [CrossRef
[36] 魏超, 张平竹, 李小六. 检测一氧化碳分子荧光探针的研究进展[J]. 有机化学, 2019, 39(12): 3375-3383.
[37] Michel, B.W., Lippert, A.R. and Chang, C.J. (2012) A Reaction-Based Fluorescent Probe for Selective Imaging of Carbon Monoxide in Living Cells using a Palladium-Mediated Carbonylation. Journal of American Chemical Society, 134, 15668-15671. [Google Scholar] [CrossRef] [PubMed]
[38] Liu, K., Kong, X., Ma, Y. and Lin, W. (2017) Rational Design of a Robust Fluorescent Probe for the Detection of Endogenous Carbon Monoxide in Living Zebrafish Embryos and Mouse Tissue. Angewandte Chemie International Edition, 56, 13489-13492. [Google Scholar] [CrossRef] [PubMed]
[39] Zhou, E., Gong, S., Xia, Q. and Feng, G. (2021) In Vivo Imaging and Tracking Carbon Monoxide-Releasing Molecule-3 with an NIR Fluorescent Probe. ACS Sensors, 26, 1312-1320. [Google Scholar] [CrossRef] [PubMed]