The chemical cross-linking applications and perspectives in dentine adhesive

doi:10.3877/cma.j.issn.1674-1366.2019.03.001

Abstract

Abstract:

The degradation of exposed collagen at the bottom of resin-dentine hybrid layers is attributed to adhesive failure of resin restoration. By facilitating additional molecular bond or hydrogen bond within dentine collagen in hybrid layers, the application of chemical cross-linking has been confirmed to increase the mechanical performance and resistance against the enzymic degradation of dentine matrix, which results in the improvement on durability of the resin-dentine bonding. Hence, we analyse and discuss the mechanism and applications in dentine adhesive of chemical cross-linking.

Key words: Collagen, Dentine, Adhesives, Cross-linking reagents

Lisha Gu, Qian Wu. The chemical cross-linking applications and perspectives in dentine adhesive[J]. Chinese Journal of Stomatological Research(Electronic Edition), 2019, 13(03): 129-135.

/ / Recommend

Add to citation manager EndNote|Ris|BibTeX

URL: https://zhkqyxyjzz.cma-cmc.com.cn/EN/10.3877/cma.j.issn.1674-1366.2019.03.001

https://zhkqyxyjzz.cma-cmc.com.cn/EN/Y2019/V13/I03/129

References 71

[1]	Yang J, Ding C, Huang L, et al. The preparation of poly（γ-glutamic acid）-NHS ester as a natural cross-linking agent of collagen[J]. Int J Biol Macromol, 2017(97): 1-7. DOI: 10.1016/j.ijbIomac.2016.12.070.
[2]	Farjadnia M, Naderan M. Corneal cross - linking treatment of keratoconus[J]. Oman J Ophthalmol, 2015, 8(2): 86-91. DOI: 10.4103/0974-620X.159105.
[3]	Yamauchi M, Shiiba M. Lysine hydroxylation and crosslinking of collagen[J]. Methods Mol Biol, 2002(194): 277-290. DOI: 10.1385/1-59259-181-7:277.
[4]	Zeugolis DI, Paul GR, Attenburrow G. Cross-linking of extruded collagen fibers -- a biomimetic three - dimensional scaffold for tissue engineering applications[J]. J Biomed Mater Res A, 2009, 89(4): 895-908. DOI: 10.1002/jbm.a.32031.
[5]	Collighan RJ, Griffin M. Transglutaminase 2 cross - linking of matrix proteins: biological significance and medical applications[J]. Amino Acids, 2009, 36(4): 659-670. DOI: 10.1007/s00726-008-0190-y.
[6]	Oryan A, Kamali A, Moshiri A, et al. Chemical crosslinking of biopolymeric scaffolds: Current knowledge and future directions of crosslinked engineered bone scaffolds[J]. Int J Biol Macromol, 2018, 107(Pt A): 678-688. DOI: 10.1016/j.ijbiomac.2017.08.184.
[7]	Gu L, Shan T, Ma Y, et al. Novel Biomedical Applications of Crosslinked Collagen[J]. Trends Biotechnol, 2019, 37(5): 464-491. DOI: 10.1016/j.tibtech.2018.10.007
[8]	Liu Y, Tjaderhane L, Breschi L, et al. Limitations in Bonding to Dentin and Experimental Strategies to Prevent Bond Degradation[J]. J Dent Res, 2011, 90(8): 953-968. DOI: 10.1177%2F0022034510391799.
[9]	Hu Y, Liu L, Gu Z, et al. Modification of collagen with a natural derived cross - linker, alginate dialdehyde[J]. Carbohyd Polym, 2014(102): 324-332. DOI: 10.1016/j.carbpol.2013.11.050.
[10]	Hass V, Luque-Martinez IV, Gutierrez MF, et al. Collagen cross - linkers on dentin bonding: Stability of the adhesive interfaces, degree of conversion of the adhesive, cytotoxicity and in situ MMP inhibition[J]. Dent Mater, 2016, 32(6): 732-741. DOI: 10.1016/j.dental.2016.03.008.
[11]	Furst W, Banerjee A. Release of glutaraldehyde from an albumin-glutaraldehyde tissue adhesive causes significant in vitro and in vivo toxicity[J]. Ann Thorac Surg, 2005, 79(5): 1522-1528, 1529. DOI: 10.1016/j.athoracsur.2004.11.054.
[12]	Olde DL, Dijkstra PJ, van Luyn MJ, et al. Cross - linking of dermal sheep collagen using a water - soluble carbodiimide[J]. Biomaterials, 1996, 17(8): 765-773. DOI: 10.1016/0142-9612(96)81413-X.
[13]	Min Zhang, Wu K, Li G. Interactions of collagen molecules in the presence of N-hydroxysuccinimide activated adipic acid（NHS-AA）as a crosslinking agent[J]. Int J Biol Macromol, 2011(49): 847-854. DOI: 10.1016/j.ijbiomac.2011.08.007.
[14]	汪凌云，王迎军，杨春蓉. EDC/NHS交联对胶原物理化学性能的影响[J]. 华南理工大学学报（自然科学版），2007，35(12)：66-70.
[15]	钟招汉. 胶原蛋白改性棉织物的研究[D]. 华南理工大学，2011.
[16]	彭燕. 氨基酸与环氧化合物反应的研究[D]. 山东轻工业学院，2006.
[17]	王昆，朱蕾，蔡道章，等. 生物型人工韧带的制备及体外检测[J]. 解剖学研究，2007，29(3)：202-205.
[18]	周磊，陈敏，程海明. 胶原蛋白硫代改性方法的研究[J]. 皮革科学与工程，2005，15(3)：12-16.
[19]	李国英，罗怡，张铭让. 乙醛酸与胶原的作用机理研究[J]. 皮革科学与工程，2000，10(2)：13-16.
[20]	薛新顺，罗发兴，罗志刚，等. 胶原的化学交联改性技术研究进展[J]. 皮革科学与工程，2006，16(6)：55-59.
[21]	Madhavan K, Belchenko D, Motta A, et al. Evaluation of composition and crosslinking effects on collagen-based composite constructs[J]. Acta Biomaterialia, 2010, 6(4): 1413-1422. DOI: 10.1016/j.actbio.2009.09.028.
[22]	Hwang YJ, Larsen J, Krasieva TB, et al. Effect of genipin crosslinking on the optical spectral properties and structures of collagen hydrogels[J]. ACS Appl Mater Interfaces, 2011, 3(7): 2579-2584. DOI: 10.1021/am200416h.
[23]	Mitra T, Sailakshmi G, Gnanamani A, et al. Preparation and characterization of a thermostable and biodegradable biopolymers using natural cross-linker[J]. Int J Biol Macromol, 2011, 48(2): 276-285. DOI: 10.1016/j.ijbiomac.2010.11.011.
[24]	Hiraishi N, Maruno T, Tochio N, et al. Hesperidin interaction to collagen detected by physico - chemical techniques[J]. Dent Mater, 2017, 33(1): 33-42. DOI: 10.1016/j.dental.2016.09.035.
[25]	Madhan B, Subramanian V, Rao JR, et al. Stabilization of collagen using plant polyphenol: role of catechin[J]. Int J Biol Macromol, 2005, 37(1-2): 47-53. DOI: 10.10116/j.ijbiomac.2005.08.005
[26]	Hsu YC, Kuo YW, Chang YC, et al. Rheological and dynamic integrity of simulated degenerated disc and consequences after cross-linker augmentation[J]. Spine（Phila Pa 1976）, 2013, 38(23): E1446-E1453. DOI: 10.1097/BRS.0b013e3182a3d09d.
[27]	Zhang M, Li J, Ding C, et al. The rheological and structural properties of fish collagen cross-linked by N-hydroxysuccinimide activated adipic acid[J]. Food Hydrocolloids, 2013, 30(2): 504-511. DOI: 10.1016/j.foodhyd.2012.07.015.
[28]	Moreira MA, Souza NO, Sousa RS, et al. Efficacy of new natural biomodification agents from Anacardiaceae extracts on dentin collagen cross - linking[J]. Dent Mater, 2017(33): 1103-1109. DOI: 10.1016/j.dental.2017.07.003.
[29]	Seseogullari-Dirihan R, Mutluay MM, Vallittu P, et al. Effect of pretreatment with collagen crosslinkers on dentin protease activity[J]. Dent Mater, 2015, 31(8): 941-947. DOI: 10.1016/j.dental.2015.05.002.
[30]	Xiang J, Liu P, Zheng X, et al. The effect of riboflavin/UVA cross - linking on anti - degeneration and promoting angiogenic capability of decellularized liver matrix[J]. J Biomed Mater Res A, 2017, 105(10): 2662-2669. DOI: 10.1002/jbm.a.36126.
[31]	Xu Y, Huang C, Li L. In vitro enzymatic degradation of a biological tissue fixed by alginate dialdehyde[J]. Carbohyd Polym, 2013(95): 148-154. DOI: 10.1016/j.carbpol.2013.03.021.
[32]	Dharunya G, Duraipandy N, Lakra R, et al. Curcumin cross - linked collagen aerogels with controlled anti-proteolytic and pro-angiogenic efficacy[J]. Biomed Mater, 2016, 11(4): 45011. DOI: 10.1088/1748-6041/11/4/045011.
[33]	Zhang J, Deng A, Zhou A, et al. Comparison of two proanthocy-anidin cross-linked recombinant human collagen-peptide（RHC）- chitosan scaffolds[J]. J Biomater Sci Polym Ed, 2015, 26(10): 585-599. DOI: 10.1080/09205063.2015.1047667.
[34]	Chiang Y, Chen Y, Chuang S, et al. Riboflavin-ultraviolet-A - induced collagen cross - linking treatments in improving dentin bonding[J]. Dent Mater, 2013, 29(6): 682-692. DOI: 10.1016/j.dental.2013.03.015.
[35]	Castellan CS, Pereira PN, Grande RH, et al. Mechanical characterization of proanthocyanidin - dentin matrix interaction[J]. Dent Mater, 2010(26): 968-973. DOI: 10.1016/j.dental.2010.06.001.
[36]	Boukpessi T, Menashi S, Camoin L, et al. The effect of stromelysin-1（MMP-3）on non-collagenous extracellular matrix proteins of demineralized dentin and the adhesive properties of restorative resins[J]. Biomaterials, 2008, 29(33): 4367-4373. DOI: 10.1016/j.biomaterials.2008.07.035.
[37]	Mazzoni A, Mannello F, Tay FR, et al. Zymographic analysis and characterization of MMP - 2 and - 9 forms in human sound dentin[J]. J Dent Res, 2007, 86(5): 436-440. DOI: 10.1177%2F154405910708600509.
[38]	Santos J, Carrilho M, Tervahartiala T, et al. Determination of matrix metalloproteinases in human radicular dentin[J]. J Endod, 2009, 35(5): 686-689. DOI: 10.1016/j.joen.2009.02.003.
[39]	Tersariol IL, Geraldeli S, Minciotti CL, et al. Cysteine cathepsins in human dentin-pulp complex[J]. J Endod, 2010, 36(3): 475-481. DOI: 10.1016/j.joen.2009.12.034.
[40]	Mazzoni A, Pashley DH, Nishitani Y, et al. Reactivation of inactivated endogenous proteolytic activities in phosphoric acid - etched dentine by etch - and - rinse adhesives[J]. Biomaterials, 2006, 27(25): 4470-4476. DOI: 10.1016/j.biomaterials.2006.01.040.
[41]	Nishitani Y, Yoshiyama M, Wadgaonkar B, et al. Activation of gelatinolytic/collagenolytic activity in dentin by self - etching adhesives[J]. Eur J Oral Sci, 2006, 114(2): 160-166. DOI: 10.1111/j.1600-0722.2006.00342.x
[42]	Tezvergil-Mutluay A, Mutluay M, Seseogullari-Dirihan R, et al. Effect of phosphoric acid on the degradation of human dentin matrix[J]. J Dent Res, 2013, 92(1): 87-91. DOI: 10.1177/0022034512466264.
[43]	Seseogullari-Dirihana R, Mutluay MM, Pashley DH, et al. Is the inactivation of dentin proteases bycrosslinkers reversible[J].Dent Mater, 2017(33): e62-e68. DOI: 10.1016/j.dental.2016.09.036.
[44]	Seseogullari-Dirihana R, Apolloniob F, Mazzonic A, et al. Use of crosslinkers to inactivate dentin MMPs[J]. Dent Mater, 2016(32): 423-432. DOI: 10.1016/j.dental.2015.12.012.
[45]	O′Farrell TJ, Guo R, Hasegawa H, et al. Matrix metalloproteinase-1 takes advantage of the induced fit mechanism to cleave the triple - helical type I collagen molecule[J]. Biochemistry, 2006, 45(51): 15411-15418. DOI: 10.1021/bi060849d.
[46]	Malla N, Sjoli S, Winberg JO, et al. Biological and pathobiological functions of gelatinase dimers and complexes[J]. Connect Tissue Res, 2008, 49(3): 180-184. DOI: 10.1080/03008200802151755.
[47]	Liu Y, Chen M, Yao X, et al. Enhancement in dentin collagen′s biological stability after proanthocyanidins treatment in clinically relevant time periods[J]. Dent Mater, 2013, 29(4): 485-92. DOI: 10.1016/j.dental.2013.01.013.
[48]	Sung HW, Chang Y, Liang IL, et al. Fixation of biological tissues with a naturally occurring crosslinking agent: fixation rate and effects of pH, temperature, and initial fixative concentration[J]. J Biomed Mater Res, 2000, 52(1): 77-87.
[49]	Vizarova K, Bakos D, Rehakova M, et al. Modification of layered atelocollagen: enzymatic degradation and cytotoxicity evaluation[J]. Biomaterials, 1995, 16(16): 1217-1221. DOI: 10.1016/0142-9612(95)98127-Z.
[50]	Scheffel DL, Hebling J, Scheffel RH, et al. Stabilization of dentin matrix after cross - linking treatments, in vitro[J]. Dent Mater, 2014, 30(2): 227-233. DOI: 10.1016/j.dental.2013.11.007.
[51]	Cilli R, Prakki A, de Araujo PA, et al. Influence of glutaraldehyde priming on bond strength of an experimental adhesive system applied to wet and dry dentine[J]. J Dent, 2009, 37(3): 212-218. DOI: 10.1016/j.jdent.2008.11.017.
[52]	Zhou J, Chiba A, Scheffel DL, et al. Cross-linked dry bonding: A new etch-and-rinse technique[J]. Dent Mater, 2016, 32(9): 1124-1132. DOI: 10.1016/j.dental.2016.06.014.
[53]	Zhang Z, Beitzel D, Majd H, et al. Effect of carbodiimide on the fatigue crack growth resistance of resin - dentin bonds[J]. Dent Mater, 2016, 32(2): 211-222. DOI: 10.1016/j.dental.2015.11.024.
[54]	Zhang Z, Mutluay M, Tezvergil-Mutluay A, et al. Effects of EDC crosslinking on the stiffness of dentin hybrid layers evaluated by nanoDMA over time[J]. Dent Mater, 2017, 33(8): 904-914. DOI: 10.1016/j.dental.2017.04.006.
[55]	Dos SP, Karol S, Bedran-Russo AK. Long-term nano-mechanical properties of biomodified dentin-resin interface components[J]. J Biomech, 2011, 44(9): 1691-1694. DOI: 10.1016/j.jbiomech.2011.03.030.
[56]	Sharma P, Nagpal R, Tyagi SP, et al. Bonding efficacy of etch- and - rinse adhesives after dentin biomodification using ethanol saturation and collagen cross - linker pretreatment[J]. J Conserv Dent, 2015, 18(4): 331-336. DOI: 10.4103/0972-0707.159751.
[57]	Mazzoni A, Angeloni V, Comba A, et al. Cross-linking effect on dentin bond strength and MMPs activity[J]. Dent Mater, 2018, 34(2): 288-295. DOI: 10.1016/j.dental.2017.11.009.
[58]	Pinto CF, Berger SB, Cavalli V, et al. Influence of chemical and natural cross - linkers on dentin bond strength of self - etching adhesives[J]. Int J Adhes Adhes, 2015(60): 117-122.
[59]	窦祈，方明，刘瑞瑞，等. 原花青素对两步法自酸蚀粘接系统即刻粘接性能的影响[C]//2012年口腔粘接修复学术研讨会论文集，西安，2012.
[60]	Epasinghe DJ, Yiu CK, Burrow MF, et al. Effect of proanthocy-anidin incorporation into dental adhesive resin on resin - dentine bond strength[J]. J Dent, 2012, 40(3): 173-180. DOI: 10.1016/j.jdent.2011.11.013.
[61]	de Macedo FAA, Souza NO, Lemos MVS, et al. Dentin bonding and physicochemical properties of adhesives incorporated with epigallocatechin-3-gallate[J]. Odontology, 2019, 107(1): 23-28. DOI: 10.1007/s10266-018-0367-0.
[62]	方明，刘瑞瑞，李芳，等. 交联剂预处理对牙本质粘接性能的影响[Z]. 北京：2011.
[63]	方明，刘瑞瑞，李芳，等. 葡萄籽提取物对脱矿牙本质极限拉伸强度及树脂-牙本质粘接强度的影响[J]. 实用口腔医学杂志，2012，28(6)：703-708. DOI：10.3969/j.issn.1001-3733.2012.06.08.
[64]	沙鑫家，王玉睿，周三玲，等. 京尼平预处理对脱矿牙本质胶原机械性能的影响[J]. 牙体牙髓牙周病学杂志，2014，24(8)：451-454. DOI：10.3969/j.issn.1005-2593.2014.08.004.
[65]	Leme AA, Vidal CM, Hassan LS, et al. Potential role of surface wettability on the long-term stability of dentin bonds after surface biomodification[J]. J Biomech, 2015, 48(10): 2067-2071. DOI: 10.1016/j.jbiomech.2015.03.016.
[66]	Islam MS, Hiraishi N, Nassar M, et al. Effect of hesperidin incorporation into a self - etching primer on durability of dentin bond[J]. Dent Mater, 2014, 30(11): 1205-1212. DOI: 10.1016/j.dental.2014.08.371.
[67]	Parise Gré C, Pedrollo Lise D, Ayres AP, et al. Do collagen cross - linkers improve dentin′s bonding receptiveness？[J]. Dent Mater, 2018, 34(11): 1679-1689. DOI: 10.1016/j.dental.2018.08.303.
[68]	Mazzoni A, Angeloni V, Apolonio FM, et al. Effect of carbodiimide（EDC）on the bond stability of etch - and - rinse adhesive systems[J]. Dent Mater, 2013, 29(10): 1040-7. DOI: 10.1016/j.dental.2013.07.010.
[69]	Islam S, Hiraishi N, Nassar M, et al. Effect of natural cross - linkers incorporation in a self - etching primer on dentine bond strength[J]. J Dent, 2012, 40(12): 1052-1059. DOI: 10.1016/j.jdent.2012.08.015.
[70]	Hass V, Luque-Martinez IV, Gutierrez MF, et al. Collagen cross - linkers on dentin bonding: Stability of the adhesive interfaces, degree of conversion of the adhesive, cytotoxicity and in situ MMP inhibition[J]. Dent Mater, 2016, 32(6): 732-741. DOI: 10.1016/j.dental.2016.03.008.
[71]	窦祈. 原花青素不同添加方式对两步法自酸蚀粘接系统粘接性能影响的研究[D]. 西安：第四军医大学，2013.

Please choose a citation manager

Content to export