CoChat
Sign Up
Cited by 19Dental materials and restorationsPolymer Surface Interaction StudiesEpoxy Resin Curing Processes

Oxidized Dopamine Acrylamide Primer to Achieve Durable Resin–Dentin Bonding

Open access
Wu, Leping, Shao, Hui, Tao, Yang, Wu, Jingya, Wang, Xinhui, Nian, Qiufeng, Zheng, Shunli, Cao, Chris Ying +4 more·2023·Research
DOI 10.34133/research.0101PMC PMC10079285
Open this paper in CoChat — free account

Abstract

The durability of the resin–dentin bonding interface is a key issue in clinical esthetic dentistry. Inspired by the extraordinary bioadhesive properties of marine mussels in a wet environment, we designed and synthetized N-2-(3,4-dihydroxylphenyl) acrylamide (DAA) according to the functional domain of mussel adhesive proteins. DAA’s properties of collagen cross-linking, collagenase inhibition, inducing collagen mineralization in vitro, and as a novel prime monomer for clinical dentin adhesion use, its optimal parameters, and effect on the adhesive longevity and the bonding interface’s integrity and mineralization, were evaluated in vitro and in vivo. The results showed that oxide DAA can inhibit the activity of collagenase and cross collagen fibers to improve the anti-enzymatic hydrolysis of collagen fibers and induce intrafibrillar and interfibrillar collagen mineralization. As a primer used in the etch-rinse tooth adhesive system, oxide DAA can improve the durability and integrity of the bonding interface by anti-degradation and mineralization of the exposed collagen matrix. Oxidized DAA (OX-DAA) is a promising primer for improving dentin durability; using 5% OX-DAA ethanol solution and treating the etched dentin surface for 30 s is the optimal choice when used as a primer in the etch-rinse tooth adhesive system.

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Integrity signals

Registry

Crossref · 10.34133/research.0101

Cites

2 of 2 references verified0 citation errors · 0 not checkable

Statistics

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

  • PDA pretreatment or incorporation into adhesive formulations significantly enhances both the mechanical strength and the resistance to hydrolytic and enzymatic degradation of the dentin adhesive interface, thereby improving the long-term clinical performance of dental restorations.

    “As a result, both the mechanical strength and resistance to hydrolytic and enzymatic degradation of the adhesive interface are significantly enhanced, thereby improving the long-term clinical performance of dental restorations.”

    From Polydopamine-Based Biomaterials in Oral Medicine: Applications, Mechanisms, and Translational Challenges (2026) · cites this paper as [30]

    The Results (no page supplied) report that oxidized dopamine acrylamide (OX-DAA) pretreatment preserved resin–dentin bond strength after thermocycling, though it did not significantly increase immediate bond strength. The Discussion (no page supplied) describes resistance to resin hydrolysis and collagen degradation. The paper studies OX-DAA, not PDA pretreatment or its incorporation into adhesive formulations, and it does not demonstrate improved long-term clinical performance of restorations. (LLM, conf=0.88)

    Experimental — accuracy not yet measured

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Cites

Flagged first, then by citations

Research works printed but not linked: 54

  1. [1]De MJ, Van LK, Peumans M, Poitevin A, Lambrechts P, Braem M, Van MB. A critical review of the durability of adhesion to tooth tissue: Methods and results. J Dent Res. 2005; 84(2): 118– 132. 15668328
  2. [2]Montagner AF, Sarkis-Onofre R, Pereira-Cenci T, Cenci MS. MMP inhibitors on dentin stability: A systematic review and meta-analysis. J Dent Res. 2014; 93(8): 733– 743. 24935066 PMC4293757
  3. [3]Inoue S, Vargas M, Abe Y, Yoshida Y, Lambrechts P, Vanherle G, Sano H, Van Meerbeek B. Microtensile bond strength of eleven contemporary adhesives to dentin. J Adhes Dent. 2001; 3(3): 237– 245. 11803711
  4. [4]Wang Y, Spencer P. Quantifying adhesive penetration in adhesive/dentin interface using confocal Raman microspectroscopy. J Biomed Mater Res. 2002; 59(1): 46– 55. 11745536
  5. [5]Nakabayashi N, Nakamura M, Yasuda N. Hybrid layer as a dentin-bonding mechanism. J Esthet Dent. 1991; 3(4): 133– 138. 1817582
  6. [6]Pashley DH, Tay FR, Carvalho RM, Rueggeberg FA, Agee KA, Carrilho M, Donnelly AM, García-Godoy F. From dry bonding to water-wet bonding to ethanol-wet bonding. A review of the interactions between dentin matrix and solvated resins using a macromodel of the hybrid layer. Am J Dent. 2007; 20(1): 7– 20. 17380802
  7. [7]Thompson JM, Agee K, Sidow SJ, McNally K, Lindsey K, Borke J, Elsalanty M, Tay FR, Pashley DH. Inhibition of endogenous dentin matrix metalloproteinases by ethylenediaminetetraacetic acid. J Endod. 2012; 38(1): 62– 65. 22152622 PMC3240849
  8. [8]Carrilho MR, Geraldeli S, Tay F, De-Goes MF, Carvalho RM, Breschi L, Mazzoni A, Reis AF, Tjaderhane L, Pashley D. In vivo preservation of the hybrid layer by chlorhexidine. J Dent Res. 2007; 86(6): 529– 533. 17525352
  9. [9]Imazato S, Tay FR, Kaneshiro AV, Takahashi Y, Ebisu S. An in vivo evaluation of bonding ability of comprehensive antibacterial adhesive system incorporating MDPB. Dent Mater. 2007; 23(2): 170– 176. 16469372
  10. [11]Kato MT, Leite AL, Hannas AR, Calabria MP, Magalhaes AC, Pereira JC, Buzalaf MA. Impact of protease inhibitors on dentin matrix degradation by collagenase. J Dent Res. 2012; 91(12): 1119– 1123. 23023765
  11. [12]Tjaederhane L, Nascimento FD, Breschi L, Mazzoni A, Tersariol I, Geraldeli S, Tezvergil-Muiluay A, Carrilho M, Carvalho RM, Tay FR, et al. Strategies to prevent hydrolytic degradation of the hybrid layer-A review. Dent Mater. 2013; 29(10): 999– 1011. 23953737 PMC3899917
  12. [13]Tezvergil-Mutluay A, Mutluay MM, Agee KA, Seseogullari-Dirihan R, Hoshika T, Cadenaro M, Breschi L, Vallittu P, Tay FR, Pashley DH. Carbodiimide cross-linking inactivates soluble and matrix-bound MMPs, in vitro. J Dent Res. 2012; 91(2): 192– 196. 22058118 PMC3261119
  13. [14]Liu Y, Dusevich V, Wang Y. Proanthocyanidins rapidly stabilize the demineralized dentin layer. J Dent Res. 2013; 92(8): 746– 752. 23723381 PMC3711569
  14. [15]Jackson JK, Zhao J, Wong W, Burt HM. The inhibition of collagenase induced degradation of collagen by the galloyl-containing polyphenols tannic acid, epigallocatechin gallate and epicatechin gallate. J Mater Sci Mater Med. 2010; 21(5): 1435– 1443. 20162329
  15. [16]Cova A, Breschi L, Nato F, Ruggeri A Jr, Carrilho M, Tjaderhane L, Prati C, Di Lenarda R, Tay FR, Pashley DH, et al. Effect of UVA-activated riboflavin on dentin bonding. J Dent Res. 2011; 90(12): 1439– 1445. 21940521 PMC3215759
  16. [17]Tay FR, Pashley DH. Guided tissue remineralisation of partially demineralised human dentine. Biomaterials. 2008; 29(8): 1127– 1137. 18022228
  17. [18]Gu LS, Huffman BP, Arola DD, Kim YK, Mai S, Elsalanty ME, Ling JQ, Pashley DH, Tay FR. Changes in stiffness of resin-infiltrated demineralized dentin after remineralization by a bottom-up biomimetic approach. Acta Biomater. 2010; 6(4): 1453– 1461. 19887126 PMC2830350
  18. [19]Hofman AH, van Hees IA, Yang J, Kamperman M. Bioinspired underwater adhesives by using the supramolecular toolbox. Adv Mater. 2018; 30(19): Article e1704640. 29356146
  19. [20]Lee H, Dellatore SM, Miller WM, Messersmith PB. Mussel-inspired surface chemistry for multifunctional coatings. Science. 2007; 318(5849): 426– 430. 17947576 PMC2601629
  20. [21]Lee D, Bae H, Ahn J, Kang T, Seo DG, Hwang DS. Catechol-thiol-based dental adhesive inspired by underwater mussel adhesion. Acta Biomater. 2020; 103: 92– 101. 31811956
  21. [22]Shokri M, Dalili F, Kharaziha M, Baghaban Eslaminejad M, Ahmadi Tafti H. Strong and bioactive bioinspired biomaterials, next generation of bone adhesives. Adv Colloid Interf Sci. 2022; 305: 102706. 35623113
  22. [23]Fang H, Li QL, Han M, Mei ML, Chu CH. Anti-proteolytic property and bonding durability of mussel adhesive protein-modified dentin adhesive interface. Dent Mater. 2017; 33(10): 1075– 1083. 28754254
  23. [24]Wu LP, Shao H, Fang ZH, Zhao YC, Cao CY, Li QL. Mechanism and effects of polyphenol derivatives for modifying collagen. ACS Biomater Sci Eng. 2019; 5(9): 4272– 4284. 33417783
  24. [25]Wu LP, Wang QQ, Li YZ, Yang MM, Dong ML, He XX, Zheng SL, Cao CY, Zhou Z, Zhao YC, et al. A dopamine acrylamide molecule for promoting collagen biomimetic mineralization and regulating crystal growth direction. ACS Appl Mater Interfaces. 2021; 13(33): 39142– 39156. 34433244
  25. [26]Yang B, Adelung R, Ludwig K, Bössmann K, Pashley DH, Kern M. Effect of structural change of collagen fibrils on the durability of dentin bonding. Biomaterials. 2005; 26(24): 5021– 5031. 15769538
  26. [27]Lee S, González-Cabezas C, Kim K, Kim K, Kuroda K. Catechol-functionalized synthetic polymer as a dental adhesive to contaminated dentin surface for a composite restoration. Biomacromolecules. 2015; 16(8): 2265– 2275. 26176305 PMC4534835
  27. [28]Olszta MJ, Cheng XG, Jee SS, Kumar R, Kim Y, Kaufman MJ, Douglas EP, Gower LB. Bone structure and formation: A new perspective. Mater Sci Eng R Rep. 2007; 58(3–5): 77– 116.
  28. [29]Su X, Sun K, Cui FZ, Landis WJ. Organization of apatite crystals in human woven bone. Bone. 2003; 32(2): 150– 162. 12633787
  29. [30]Silverman HG, Roberto FF. Understanding marine mussel adhesion. Mar Biotechnol. 2007; 9(6): 661– 681. PMC2100433 17990038
  30. [31]Balkenende DWR, Winkler SM, Messersmith PB. Marine-inspired polymers in medical adhesion. Eur Polym J. 2019; 116: 134– 143. 32831361 PMC7434107
  31. [32]Miller DR, Spahn JE, Waite JH. The staying power of adhesion-associated antioxidant activity in Mytilus californianus. J R Soc Interface. 2015; 12(111): Article 20150614. 26468070 PMC4614499
  32. [33]Valois E, Mirshafian R, Waite JH. Phase-dependent redox insulation in mussel adhesion. Sci Adv. 2020; 6(23): Article eaaz6486. 32537498 PMC7269650
  33. [34]Waite JH. Mussel adhesion - essential footwork. J Exp Biol. 2017; 220(Pt 4): 517– 530. 28202646 PMC5312731
  34. [35]Nagase H, Fushimi K. Elucidating the function of non catalytic domains of collagenases and aggrecanases. Connect Tissue Res. 2008; 49(3): 169– 174. 18661336
  35. [36]Chung L, Dinakarpandian D, Yoshida N, Lauer-Fields JL, Fields GB, Visse R, Nagase H. Collagenase unwinds triple-helical collagen prior to peptide bond hydrolysis. EMBO J. 2004; 23(15): 3020– 3030. 15257288 PMC514933
  36. [37]Sabatini C, Pashley DH. Mechanisms regulating the degradation of dentin matrices by endogenous dentin proteases and their role in dental adhesion. A review. Am J Dent. 2014; 27(4): 203– 214. 25831604 PMC4412266
  37. [38]Pashley DH, Tay FR, Yiu C, Hashimoto M, Breschi L, Carvalho RM, Ito S. Collagen degradation by host-derived enzymes during aging. J Dent Res. 2004; 83(3): 216– 221. 14981122
  38. [39]Monahan J, Wilker JJ. Specificity of metal ion cross-linking in marine mussel adhesives. Chem Commun. 2003; 21(14): 1672– 1673. 12877496
  39. [41]Kim S, Park CB. Dopamine-induced mineralization of calcium carbonate vaterite microspheres. Langmuir. 2010; 26(18): 14730– 14736. 20795669
  40. [42]Hong GS, Shen LD, Wang M, Yang Y, Wang XF, Zhu MF, Hsiao BS. Nanofibrous polydopamine complex membranes for adsorption of lanthanum (III) ions. Chem Eng J. 2014; 244: 307– 316.
  41. [43]Waite JH, Housley TJ, Tanzer ML. Peptide repeats in a mussel glue protein: Theme and variations. Biochemistry. 1985; 24(19): 5010– 5014. 4074674
  42. [44]Waite JH, Qin XX, Coyne KJ. The peculiar collagens of mussel byssus. Matrix Biol. 1998; 17(2): 93– 106. 9694590
  43. [45]Li JH, Yang JJ, Li JY, Chen L, Liang KN, Wu W, Chen XY, Li JS. Bioinspired intrafibrillar mineralization of human dentine by PAMAM dendrimer. Biomaterials. 2013; 34(28): 6738– 6747. 23787113
  44. [46]Liu Y, Li N, Qi YP, Dai L, Bryan TE, Mao J, Pashley DH, Tay FR. Intrafibrillar collagen mineralization produced by biomimetic hierarchical nanoapatite assembly. Adv Mater. 2011; 23(8): 975– 980. 21341310 PMC3137871
  45. [47]Kim YK, Gu LS, Bryan TE, Kim JR, Chen L, Liu Y, Yoon JC, Breschi L, Pashley DH, Tay FR. Mineralisation of reconstituted collagen using polyvinylphosphonic acid/polyacrylic acid templating matrix protein analogues in the presence of calcium, phosphate and hydroxyl ions. Biomaterials. 2010; 31(25): 6618– 6627. 20621767 PMC2904357
  46. [48]Kim JH, Arola DD, Gu LS, Kim YK, Mai S, Liu Y, Pashley DH, Tay FR. Functional biomimetic analogs help remineralize apatite-depleted demineralized resin-infiltrated dentin via a bottom-up approach. Acta Biomater. 2010; 6(7): 2740– 2750. 20045745 PMC2874105
  47. [49]Nudelman F, Pieterse K, George A, Bomans PH, Friedrich H, Brylka LJ, Hilbers PA, de With G, Sommerdijk NA. The role of collagen in bone apatite formation in the presence of hydroxyapatite nucleation inhibitors. Nat Mater. 2010; 9(12): 1004– 1009. 20972429 PMC3084378
  48. [50]Toroian D, Lim JE, Price PA. The size exclusion characteristics of type I collagen: Implications for the role of noncollagenous bone constituents in mineralization. J Biol Chem. 2007; 282(31): 22437– 22447. 17562713
  49. [51]Gordon MK, Hahn RA. Collagens. Cell Tissue Res. 2010; 339(1): 247– 257. 19693541 PMC2997103
  50. [52]Deshpande AS, Beniash E. Bio-inspired synthesis of mineralized collagen fibrils. Cryst Growth Des. 2008; 8(8): 3084– 3090. PMC2721229 19662103
  51. [53]Kim Y, Douglas EP, Gower LB. Patterning inorganic (CaCO3) thin films via a polymer-induced liquid-precursor process. Langmuir. 2007; 23(9): 4862– 4870. 17388609
  52. [54]Xu Y, Nudelman F, Eren ED, Wirix M, Cantaert B, Nijhuis WH, Hermida-Merino D, Portale G, Bomans P, Ottmann C, et al. Intermolecular channels direct crystal orientation in mineralized collagen. Nat Commun. 2020; 11(1): 5068. 33033251 PMC7545172
  53. [55]Balooch M, Habelitz S, Kinney JH, Marshall SJ, Marshall GW. Mechanical properties of mineralized collagen fibrils as influenced by demineralization. J Struct Biol. 2008; 162(3): 404– 410. 18467127 PMC2697659
  54. [56]Weiner S, Wagner HD. The material bone: Structure-mechanical function relations. Annu Rev Mater Sci. 1998; 28: 271– 298.

Cited by

Sorted by citations

Authors
Wu, L., Shao, H., Tao, Y., Wu, J., Wang, X., Nian, Q., Zheng, S., Cao, C. Y., Zhao, Y., Zhou, Z., Wong, H. M., & Li, Q.-L.
Affiliations
  • Anhui Medical University (CN)
  • Southwest Jiaotong University (CN)
  • University of Detroit Mercy (US)
  • Prince Philip Dental Hospital (CN)
  • Key Laboratory of Oral Diseases Research of Anhui Province, College and Hospital of Stomatology, Anhui Medical University, 81 Meishan Road, Hefei 230032, China.
ORCID
Venue
Research
Publisher
American Association for the Advancement of Science (AAAS)
Published
2023-01
Volume
6
Pages
0101-0101
ISSN
2639-5274 (ISSN-L)
DOI
10.34133/research.0101
PMC
PMC10079285
OpenAlex
W4327742995
Cited by
19
References
2
Citations by year
2026: 6 · 2025: 9 · 2024: 3 · 2023: 1
FWCI
4.93
Type
journal article
Language
en
Open access
Licence
cc-by
Locations
  • Research (publishedVersion, cc-by)
  • PubMed Central (publishedVersion, cc-by)
  • PubMed (publishedVersion)
  • DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
  • The HKU Scholars Hub (University of Hong Kong) (submittedVersion, cc-by-nc-nd)
Topics
  • Health Sciences › Dentistry › Orthodontics › Dental materials and restorations
  • Physical Sciences › Materials Science › Surfaces, Coatings and Films › Polymer Surface Interaction Studies
  • Physical Sciences › Engineering › Mechanical Engineering › Epoxy Resin Curing Processes
Keywords
dentin adhesion, collagen cross-linking, collagenase inhibition, collagen mineralization, esthetic dentistry

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review