Hexamethylenediamine-Mediated Polydopamine Film Deposition: Inhibition by Resorcinol as a Strategy for Mapping Quinone Targeting Mechanisms

被引:17
作者
Alfieri, Maria Laura [1 ]
Panzella, Lucia [1 ]
Oscurato, Stefano Luigi [2 ]
Salvatore, Marcella [2 ]
Avolio, Roberto [3 ]
Errico, Maria Emanuela [3 ]
Maddalena, Pasqualino [2 ]
Napolitano, Alessandra [1 ]
Ball, Vincent [4 ,5 ]
d'Ischia, Marco [1 ]
机构
[1] Univ Naples Federico II, Dept Chem Sci, Naples, Italy
[2] Univ Naples Federico II, Dept Phys Ettore Pancini, Naples, Italy
[3] Natl Council Res Italy IPCB CNR, Inst Polymers Composites & Biomat, Pozzuoli, Italy
[4] Univ Strasbourg, Fac Chirurg Dent, Strasbourg, France
[5] INSERM, Strasbourg, France
关键词
polydopamine; 5; 6-dihydroxyindole; hexamethylenediamine; coating; resorcinol; SURFACE-CHEMISTRY; DOPAMINE; PRODUCTS;
D O I
10.3389/fchem.2019.00407
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Hexamethylenediamine (HMDA) and other long chain aliphatic diamines can induce substrate-independent polymer film deposition from dopamine and several other catechols substrates at relatively low concentrations, however the mechanism of the diamine-promoted effect has remained little understood. Herein, we report data indicating that: (a) film deposition from 1 mM HMDA and dopamine is not affected by chemical oxidation with periodate but is markedly inhibited by resorcinol, which also prevents PDA film formation at 10 mM monomer concentration in the absence of HMDA; (b) N-acetylation of HMDA completely inhibits the effect on PDA film formation; (c) HMDA enables surface functionalization with 1 mM 5,6-dihydroxyindole (DHI) polymerization at pH 9.0 in a resorcinol-inhibitable manner. Structural investigation of the polymers produced from dopamine and DHI in the presence of HMDA using solid state C-13 and N-15 NMR and MALDI-MS suggested formation of covalent cross linked structures. It is concluded that HMDA enhances polydopamine adhesion by acting both on dopamine quinone and downstream, e.g., via covalent coupling with DHI. These results provide new insights into the mechanisms of PDA adhesion and disclose resorcinol as a new potent tool for targeting/mapping quinone intermediates and for controlling polymer growth.
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页数:11
相关论文
共 25 条
[1]   Structural Basis of Polydopamine Film Formation: Probing 5,6-Dihydroxyindole-Based Eumelanin Type Units and the Porphyrin Issue [J].
Alfieri, Maria L. ;
Micillo, Raffaella ;
Panzella, Lucia ;
Crescenzi, Orlando ;
Oscurato, Stefano L. ;
Maddalena, Pasqualino ;
Napolitano, Alessandra ;
Ball, Vincent ;
d'Ischia, Marco .
ACS APPLIED MATERIALS & INTERFACES, 2018, 10 (09) :7670-7680
[2]   The Chemistry of Polydopamine Film Formation: The Amine-Quinone Interplay [J].
Alfieri, Maria Laura ;
Panzella, Lucia ;
Oscurato, Stefano Luigi ;
Salvatore, Marcella ;
Avolio, Roberto ;
Errico, Maria Emanuela ;
Maddalena, Pasqualino ;
Napolitano, Alessandra ;
d'Ischia, Marco .
BIOMIMETICS, 2018, 3 (03)
[3]   Kinetics of polydopamine film deposition as a function of pH and dopamine concentration: Insights in the polydopamine deposition mechanism [J].
Ball, Vincent ;
Del Frari, Doriane ;
Toniazzo, Valerie ;
Ruch, David .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2012, 386 :366-372
[4]   Kinetic and structural analysis of the early oxidation products of dopamine -: Analysis of the interactions with α-synuclein [J].
Bisaglia, Marco ;
Mammi, Stefano ;
Bubacco, Luigi .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2007, 282 (21) :15597-15605
[5]   A simple one-step modification of various materials for introducing effective multi-functional groups [J].
Chen, Si ;
Li, Xin ;
Yang, Zhilu ;
Zhou, Shuo ;
Luo, Rifang ;
Maitz, Manfred F. ;
Zhao, Yuancong ;
Wang, Jin ;
Xiong, Kaiqin ;
Huang, Nan .
COLLOIDS AND SURFACES B-BIOINTERFACES, 2014, 113 :125-133
[6]   OXIDATIVE COUPLING OF DOPA WITH RESORCINOL AND PHLOROGLUCINOL - ISOLATION OF ADDUCTS WITH AN UNUSUAL TETRAHYDROMETHANOBENZOFURO[2,3-D]AZOCINE SKELETON [J].
CRESCENZI, O ;
NAPOLITANO, A ;
PROTA, G ;
PETER, MG .
TETRAHEDRON, 1991, 47 (32) :6243-6250
[7]  
d'Ischia M, 2018, BIOMIMETICS, DOI [10.3390/books978-3-03842-814-5, DOI 10.3390/BOOKS978-3-03842-814-5]
[8]   Building-Block Diversity in Polydopamine Underpins a Multifunctional Eumelanin-Type Platform Tunable Through a Quinone Control Point [J].
Della Vecchia, Nicola F. ;
Avolio, Roberto ;
Alfe, Michela ;
Errico, Maria E. ;
Napolitano, Alessandra ;
d'Ischia, Marco .
ADVANCED FUNCTIONAL MATERIALS, 2013, 23 (10) :1331-1340
[9]   Tris Buffer Modulates Polydopamine Growth, Aggregation, and Paramagnetic Properties [J].
Della Vecchia, Nicola Fyodor ;
Luchini, Alessandra ;
Napolitano, Alessandra ;
D'Errico, Gerardino ;
Vitiello, Giuseppe ;
Szekely, Noemi ;
d'Ischia, Marco ;
Paduano, Luigi .
LANGMUIR, 2014, 30 (32) :9811-9818
[10]   ADRENALINE OXIDATION REVISITED - NEW PRODUCTS BEYOND THE ADRENOCHROME STAGE [J].
DISCHIA, M ;
PALUMBO, A ;
PROTA, G .
TETRAHEDRON, 1988, 44 (20) :6441-6446