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Vol.5 , No. 2, Publication Date: May 10, 2018, Page: 22-28
. Several research groups have incorporated DOPA, or other compounds that contain 3,4-dihydroxybenzene, into backbone of polymeric materials, and have found the improved adhesive properties. Although current positively charged chitosan hemostatic agents have limited adhesive property, especially to wet surfaces underneath blood pool, there is no report about modifying chitosan with 3,4-dihydroxybenzene to achieve improved adhesive property so far, and the exact mechanism of chitosan’s positive charging is still unknown. Using two methods, we modified chitosan with 3,4-dihydroxybenzene. One is modifying with 3,4-dihydroxybenzaldehyde (DHBH), the other is with DOPA. The chemical structures of chitosan, Celox, DHBH, DMCTS, DOPA and DOPAMCTS were characterized with Fourier transform infrared (FTIR) spectroscopy. The coagulation test was performed to compare the hemostatic property of DMCTS and DOPAMCTS to that of chitin, chitosan and Celox. FTIR results revealed extreme similarity of chemical structures of chitosan and Celox, especially in presence of N-H bending vibration of primary amines, the incorporation of 3,4-dihydroxybenzene from DMCTS and DOPA into backbone of chitosan. The coagulation time of chitosan, Celox and DOPAMCTS was significantly shorter than that of chitin and DMCTS. The blood drops touching Celox, chitosan and DOPAMCTS particles appeared significant surface-tension phenomenon. Amino groups are crucial for chitosan to stop bleeding. Modification with 3,4-dihydroxybenzene does not impair the hemostatic property of chitosan as long as the free or protonated amino groups does not be modified. It is feasible to modify chitosan with 3,4-dihydroxybenzene to develop a novel hemostatic dressing.&picture=http://www.aascit.org/aascit/decorators/img/journal/905.jpg)
| [1] | Haibo Lu, Institute of Orthopedics of Chinese People’s Liberation Army, General Hospital of Chinese People’s Liberation Army, Beijing, China; Department of Orthopaedics, First Affiliated Hospital of Chinese People’s Liberation Army General Hospital, Beijing, China; Department of Clinic Medicine, Hospital of Chinese People’s Liberation Army Hong Kong Garrison, Hong Kong Special Administrative Region, China. |
| [2] | Shibi Lu, Institute of Orthopedics of Chinese People’s Liberation Army, General Hospital of Chinese People’s Liberation Army, Beijing, China. |
| [3] | Zhanjun Song, National Center of Biomedical Analysis, Beijing, China. |
| [4] | Ming Zhang, Institute of Chemical Defense of Chinese People’s Liberation Army, Beijing, China. |
| [5] | Jiang Peng, Institute of Orthopedics of Chinese People’s Liberation Army, General Hospital of Chinese People’s Liberation Army, Beijing, China. |
| [6] | Jian Zhang, Department of Orthopaedics, First Affiliated Hospital of Chinese People’s Liberation Army General Hospital, Beijing, China. |
| [7] | Yong Luo, Department of Clinic Medicine, Hospital of Chinese People’s Liberation Army Hong Kong Garrison, Hong Kong Special Administrative Region, China. |
| [8] | Chenyang Nie, Department of Clinic Medicine, Hospital of Chinese People’s Liberation Army Hong Kong Garrison, Hong Kong Special Administrative Region, China. |
| [9] | Sen Li, Department of Clinic Medicine, Hospital of Chinese People’s Liberation Army Hong Kong Garrison, Hong Kong Special Administrative Region, China. |
| [10] | Quanyi Guo, Institute of Orthopedics of Chinese People’s Liberation Army, General Hospital of Chinese People’s Liberation Army, Beijing, China. |
Marine organisms adhere themselves onto wet surfaces by adhesive proteins containing L-3,4-dihydroxyphenylalanine (DOPA). Several research groups have incorporated DOPA, or other compounds that contain 3,4-dihydroxybenzene, into backbone of polymeric materials, and have found the improved adhesive properties. Although current positively charged chitosan hemostatic agents have limited adhesive property, especially to wet surfaces underneath blood pool, there is no report about modifying chitosan with 3,4-dihydroxybenzene to achieve improved adhesive property so far, and the exact mechanism of chitosan’s positive charging is still unknown. Using two methods, we modified chitosan with 3,4-dihydroxybenzene. One is modifying with 3,4-dihydroxybenzaldehyde (DHBH), the other is with DOPA. The chemical structures of chitosan, Celox, DHBH, DMCTS, DOPA and DOPAMCTS were characterized with Fourier transform infrared (FTIR) spectroscopy. The coagulation test was performed to compare the hemostatic property of DMCTS and DOPAMCTS to that of chitin, chitosan and Celox. FTIR results revealed extreme similarity of chemical structures of chitosan and Celox, especially in presence of N-H bending vibration of primary amines, the incorporation of 3,4-dihydroxybenzene from DMCTS and DOPA into backbone of chitosan. The coagulation time of chitosan, Celox and DOPAMCTS was significantly shorter than that of chitin and DMCTS. The blood drops touching Celox, chitosan and DOPAMCTS particles appeared significant surface-tension phenomenon. Amino groups are crucial for chitosan to stop bleeding. Modification with 3,4-dihydroxybenzene does not impair the hemostatic property of chitosan as long as the free or protonated amino groups does not be modified. It is feasible to modify chitosan with 3,4-dihydroxybenzene to develop a novel hemostatic dressing.
Keywords
3,4-dihydroxybenzaldehyde, L-3,4-dihydroxyphenylalanine, Chitosan, 3,4-dihydroxybenzene Modified Chitosan, L-3,4-dihydroxyphenylalanine Modified Chitosan, Celox, Hemostatic Agent, FTIR
Reference
| [01] | Clay JG, Grayson JK, Zierold D. Comparative testing of new hemostatic agents in a swine model of extremity arterial and venous hemorrhage. Mil Med. 2010; 175: 280-284. |
| [02] | Arnaud F, Teranishi K, Tomori T, et al. Comparison of 10 hemostatic dressings in a groin puncture model in swine. J Vasc Surg. 2009; 50: 632-639, 631-639. |
| [03] | Otrocka-Domagała I, Jastrzębski P, Adamiak Z, et al. Safety of the long-term application of QuikClot Combat Gauze, ChitoGauze PRO and Celox Gauze in a femoral artery injury model in swine - a preliminary study. Pol J Vet Sci. 2016; 19: 337-343. |
| [04] | Kheirabadi BS, Scherer MR, Estep JS, et al. Determination of efficacy of new hemostatic dressings in a model of extremity arterial hemorrhage in swine. J Trauma. 2009; 67: 450-459, 459-460. |
| [05] | Conley SP, Littlejohn LF, Henao J, et al. Control of Junctional Hemorrhage in a Consensus Swine Model With Hemostatic Gauze Products Following Minimal Training. Mil Med. 2015; 180: 1189-1195. |
| [06] | Hatamabadi HR, AsayeshZarchi F, Kariman H, et al. Celox-coated gauze for the treatment of civilian penetrating trauma: a randomized clinical trial. Trauma Mon. 2015; 20: e23862. |
| [07] | Gegel BT, Burgert JM, Lockhart C, et al. Effects of Celox and TraumaDEX on hemorrhage control in a porcine model. AANA J. 2010; 78: 115-120. |
| [08] | Gegel B, Burgert J, Cooley B, et al. The Effects of BleedArrest, Celox, and TraumaDex on Hemorrhage Control in a Porcine Model. J Surg Res. 2010. |
| [09] | Valeri CR. Making sense of the preclinical literature on advanced hemostatic products. J Trauma. 2006; 61: 240-241, 241. |
| [10] | Nishida A, Ohkawa K, Ueda I, et al. Green mussel Pernaviridis L.: attachment behaviour and preparation of antifouling surfaces. Biomol Eng. 2003; 20: 381-387. |
| [11] | Fant C, Elwing H, Hook F. The influence of cross-linking on protein-protein interactions in a marine adhesive: the case of two byssus plaque proteins from the blue mussel. Biomacromolecules. 2002; 3: 732-741. |
| [12] | Silverman HG, Roberto FF. Understanding marine mussel adhesion. Mar Biotechnol (NY). 2007; 9: 661-681. |
| [13] | Waite JH. Marine adhesive proteins: natural composite thermosets. Int J BiolMacromol. 1990; 12: 139-144. |
| [14] | Zhao H, Waite JH. Linking adhesive and structural proteins in the attachment plaque of Mytiluscalifornianus. J Biol Chem. 2006; 281: 26150-26158. |
| [15] | Burke SA, Ritter-Jones M, Lee BP, et al. Thermal gelation and tissue adhesion of biomimetic hydrogels. Biomed Mater. 2007; 2: 203-210. |
| [16] | Lee BP, Huang K, Nunalee FN, et al. Synthesis of 3,4-dihydroxyphenylalanine (DOPA) containing monomers and their co-polymerization with PEG-diacrylate to form hydrogels. J BiomaterSciPolym Ed. 2004; 15: 449-464. |
| [17] | Lee H, Lee BP, Messersmith PB. A reversible wet/dry adhesive inspired by mussels and geckos. Nature. 2007; 448: 338-341. |
| [18] | Hu BH, Messersmith PB. Enzymatically cross-linked hydrogels and their adhesive strength to biosurfaces. OrthodCraniofac Res. 2005; 8: 145-149. |
| [19] | Yamada K, Chen T, Kumar G, et al. Chitosan based water-resistant adhesive. Analogy to mussel glue. Biomacromolecules. 2000; 1: 252-258. |
