5,6‐Dihydroxyindole Chemistry: Unexplored Opportunities Beyond Eumelanin
Abstract
5,6‐Dihydroxyindoles, the key building blocks of eumelanin biopolymers, hold promise as versatile molecular systems for the design and development of new functional aromatic scaffolds, biomimetic polymers, and nanomaterials with tailored optical and electronic properties. During the past decade, research into the photophysics, synthesis, π electron manipulation, and reaction behavior of 5,6‐dihydroxyindoles has expanded beyond the traditional boundaries of biology and medicine to involve physicists, organic chemists, and materials scientists. This review presents the latest advances in 5,6‐dihydroxyindole chemistry from a new perspective. Touching only upon themes at the periphery of eumelanin research, it seeks rather to throw light on the chemical and photophysical features of this peculiar π electron system as an unexplored conceptual and practical platform on which synthetic creativity and rational design might generate a range of chemically diverse molecular scaffolds.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
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?
The first model exhibits a "covalent bonding" polymerization fashion where DA is polymerized via 5,6-dihydroxyindole monomers following further oxidization and subsequent intermolecular cross-linking of PDA.
“The first model exhibits a “covalent bonding” polymerization fashion where DA is polymerized via 5,6-dihydroxyindole monomers following further oxidization and subsequent intermolecular cross-linking of PDA [29, 40–44].”
From Polydopamine-Assisted Surface Modification for Bone Biosubstitutes (2016) · cites this paper as [41]
Cites
Poly(aryleneethynylene)s: Syntheses, Properties, Structures, and Applications
Bunz, U. H. F. (2000) · Chemical Reviews · doi:10.1021/cr990257j · Cited by 1,661 · see citing works
Alternative Synthetic Methods through New Developments in Catalysis by Gold
Arcadi, A. (2008) · Chemical Reviews · doi:10.1021/cr068435d · Cited by 1,524 · see citing works
The physical and chemical properties of eumelanin
Meredith, P., & Sarna, T. (2006) · Pigment Cell Research · doi:10.1111/j.1600-0749.2006.00345.x · Cited by 1,033 · see citing works
Erkennung und Nachweis von Anionen: gegenwärtiger Stand und Perspektiven
Beer, P. D., & Gale, P. A. (2001) · Angewandte Chemie · doi:10.1002/1521-3757(20010202)113:3 · Cited by 511 · see citing works
Amorphous Semiconductor Switching in Melanins
McGinness, J. E., Corry, P. M., & Proctor, P. H. (1974) · Science · doi:10.1126/science.183.4127.853 · Cited by 447 · see citing works
Prota, G., & Hearing, V. J. (1993) · Melanoma Research · doi:10.1097/00008390-199304000-00014 · Cited by 381 · see citing works
Martino, G. D., Edler, M., Regina, G. L., Coluccia, A., Barbera, M. C., Barrow, D., Nicholson, R. I., Chiosis, G., Brancale, A., Hamel, E., et al. (2006) · Journal of Medicinal Chemistry · doi:10.1021/jm050809s · Cited by 368 · see citing works
Simon, J. D., & Peles, D. N. (2010) · Accounts of Chemical Research · doi:10.1021/ar100079y · Cited by 296 · see citing works
Cancer chemotherapy with indole-3-carbinol, bis(3′-indolyl)methane and synthetic analogs
Safe, S. H., Papineni, S., & Chintharlapalli, S. R. (2008) · Cancer Letters · doi:10.1016/j.canlet.2008.04.021 · Cited by 269 · see citing works
Zhang, Y., Donahue, J. P., & LI, C. ‐. (2007) · Organic Letters · doi:10.1021/ol062918m · Cited by 222 · see citing works
Kaxiras, E., Tsolakidis, A., Zonios, G., & Meng, S. (2006) · Physical Review Letters · doi:10.1103/physrevlett.97.218102 · Cited by 196 · see citing works
Powell, B. J., Baruah, T., Bernstein, N., Brake, K., McKenzie, R. H., Meredith, P., & Pederson, M. R. (2004) · The Journal of Chemical Physics · doi:10.1063/1.1690758 · Cited by 169 · see citing works
Charkoudian, L. K., & Franz, K. J. (2006) · Inorganic Chemistry · doi:10.1021/ic060014r · Cited by 147 · see citing works
Pezzella, A., Iadonisi, A., Valerio, S., Panzella, L., Napolitano, A., Adinolfi, M., & d’Ischia, M. (2009) · Journal of the American Chemical Society · doi:10.1021/ja905162s · Cited by 147 · see citing works
Self-citationRigid Rod-Shaped Polyols: Functional Nonpeptide Models for Transmembrane Proton Channels
Weiss, L. A., Sakai, N., Ghebremariam, B. T., Ni, C., & Matile, S. (1997) · Journal of the American Chemical Society · doi:10.1021/ja973126d · Cited by 141 · see citing works
Soluble Oligo‐ and Polyphenylenes
Tour, J. M. (1994) · Advanced Materials · doi:10.1002/adma.19940060303 · Cited by 141 · see citing works
Novel indolecarboxamidotetrazoles as potential antiallergy agents
Unangst, P. C., Connor, D. T., Stabler, S. R., Weikert, R. J., Carethers, M. E., Kennedy, J. A., Thueson, D. O., Chestnut, J. C., Adolphson, R. L., & Conroy, M. C. (1989) · Journal of Medicinal Chemistry · doi:10.1021/jm00126a036 · Cited by 123 · see citing works
Shao, J., Guan, Z., Yan, Y., Jiao, C., Xu, Q., & Chi, C. (2011) · The Journal of Organic Chemistry · doi:10.1021/jo1017926 · Cited by 119 · see citing works
Pezzella, A., Panzella, L., Crescenzi, O., Napolitano, A., Navaratman, S., Edge, R., Land, E. J., Barone, V., & d'Ischia, M. (2006) · Journal of the American Chemical Society · doi:10.1021/ja0650246 · Cited by 112 · see citing works
Self-citationStark, K. B., Gallas, J. M., Zajac, G. W., Golab, J. T., Gidanian, S., McIntire, T. M., & Farmer, P. J. (2005) · The Journal of Physical Chemistry B · doi:10.1021/jp046710z · Cited by 105 · see citing works
Dopaquinone redox exchange with dihydroxyindole and dihydroxyindole carboxylic acid
Edge, R., d’Ischia, M., Land, E. J., Napolitano, A., Navaratnam, S., Panzella, L., Pezzella, A., Ramsden, C. A., & Riley, P. A. (2006) · Pigment Cell Research · doi:10.1111/j.1600-0749.2006.00327.x · Cited by 98 · see citing works
Self-citationPezzella, A., Panzella, L., Natangelo, A., Arzillo, M., Napolitano, A., & d'Ischia, M. (2007) · The Journal of Organic Chemistry · doi:10.1021/jo701652y · Cited by 98 · see citing works
Self-citationPanzella, L., Pezzella, A., Napolitano, A., & d’Ischia, M. (2007) · Organic Letters · doi:10.1021/ol070268w · Cited by 90 · see citing works
Self-citation5,6-Dihydroxyindoles and indole-5,6-diones
d’Ischia, M., Napolitano, A., Pezzella, A., Land, E. J., Ramsden, C. A., & Riley, P. A. (2005) · Advances in Heterocyclic Chemistry · doi:10.1016/s0065-2725(05)89001-4 · Cited by 86 · see citing works
Self-citationGauden, M., Pezzella, A., Panzella, L., Neves‐Petersen, M. T., Skovsen, E., Petersen, S. B., Mullen, K. M., Napolitano, A., d’Ischia, M., & Sundström, V. (2008) · Journal of the American Chemical Society · doi:10.1021/ja806345q · Cited by 86 · see citing works
Self-citationGiant Artificial Ion Channels Formed by Self-Assembled, Cationic Rigid-Rodβ-Barrels
Baumeister, B., Sakai, N., & Matile, S. (2000) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20000602)39:11 · Cited by 85 · see citing works
Spectroscopic Study and Simulation from Recent Structural Models for Eumelanin: I. Monomer, Dimers
Stark, K. B., Gallas, J. M., Zajac, G. W., Eisner, M., & Golab, J. T. (2003) · The Journal of Physical Chemistry B · doi:10.1021/jp0266594 · Cited by 83 · see citing works
The syntheses of 5,6‐dihydroxyindole and some of its derivatives
Benigni, J. D., & Minnis, R. L. (1965) · Journal of Heterocyclic Chemistry · doi:10.1002/jhet.5570020413 · Cited by 81 · see citing works
Il’ichev, Y. V., & Simon, J. D. (2003) · The Journal of Physical Chemistry B · doi:10.1021/jp034702x · Cited by 80 · see citing works
Tuning electron transfer through p-phenyleneethynylene molecular wires
Atienza, C., Martı́n, N., Wielopolski, M., Haworth, N. L., Clark, T., & Guldi, D. M. (2006) · Chemical Communications · doi:10.1039/b603149h · Cited by 79 · see citing works
Wakamatsu, K., & Ito, S. (1988) · Analytical Biochemistry · doi:10.1016/0003-2697(88)90639-2 · Cited by 77 · see citing works
Sobolewski, A. L., & Domcke, W. (2007) · ChemPhysChem · doi:10.1002/cphc.200600768 · Cited by 68 · see citing works
Mee, S. P. H., Lee, V., Baldwin, J. E., & Cowley, A. R. (2004) · Tetrahedron · doi:10.1016/j.tet.2004.02.043 · Cited by 67 · see citing works
Oxidative polymerisation of 5,6-dihydroxyindole-2-carboxylic acid to melanin: A new insight
Pezzella, A., Napolitano, A., d'Ischia, M., & Prota, G. (1996) · Tetrahedron · doi:10.1016/0040-4020(96)00362-6 · Cited by 62 · see citing works
Self-citationNagarajan, R., & Perumal, P. T. (2002) · Synthetic Communications · doi:10.1081/scc-120001515 · Cited by 57 · see citing works
Singh, D. P., Malik, V., Kumar, K., Sharma, C., & Aneja, K. R. (2010) · Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy · doi:10.1016/j.saa.2010.02.044 · Cited by 56 · see citing works
Gauden, M., Pezzella, A., Panzella, L., Napolitano, A., d’Ischia, M., & Sundström, V. (2009) · The Journal of Physical Chemistry B · doi:10.1021/jp903190k · Cited by 56 · see citing works
Self-citationFeng, X., Guan, C., & Zhao, C. (2004) · Synthetic Communications · doi:10.1081/scc-120027288 · Cited by 54 · see citing works
Mechanism of Selective Incorporation of the Melanoma Seeker 2-Thiouracil into Growing Melanin
Napolitano, A., Palumbo, A., d’Ischia, M., & Prota, G. (1996) · Journal of Medicinal Chemistry · doi:10.1021/jm9605243 · Cited by 53 · see citing works
Self-citationPezzella, A., Vogna, D., & Prota, G. (2002) · Tetrahedron · doi:10.1016/s0040-4020(02)00335-6 · Cited by 52 · see citing works
Self-citationMajumdar, K. C., Samanta, S., & Chattopadhyay, B. (2008) · Tetrahedron Letters · doi:10.1016/j.tetlet.2008.10.013 · Cited by 52 · see citing works
A hydrophilic three side-chained triazatruxene as a new strong and selective G-quadruplex ligand
Ginnari‐Satriani, L., Casagrande, V., Bianco, A., Ortaggi, G., & Franceschin, M. (2009) · Organic & Biomolecular Chemistry · doi:10.1039/b904723a · Cited by 51 · see citing works
Mild and efficient iodination of aromatic and heterocyclic compounds with the NaClO2/NaI/HCl system
Lista, L., Pezzella, A., Napolitano, A., & d’Ischia, M. (2007) · Tetrahedron · doi:10.1016/j.tet.2007.10.062 · Cited by 49 · see citing works
Self-citationd’Ischia, M., Crescenzi, O., Pezzella, A., Arzillo, M., Panzella, L., Napolitano, A., & Barone, V. (2007) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2007.00249.x · Cited by 47 · see citing works
Self-citationPezzella, A., Panzella, L., Crescenzi, O., Napolitano, A., Navaratnam, S., Edge, R., Land, E. J., Barone, V., & d’Ischia, M. (2009) · The Journal of Organic Chemistry · doi:10.1021/jo900250v · Cited by 47 · see citing works
Self-citationPezzella, A., Vogna, D., & Prota, G. (2003) · Tetrahedron: Asymmetry · doi:10.1016/s0957-4166(03)00156-3 · Cited by 46 · see citing works
Self-citationd’Ischia, M., Napolitano, A., Pezzella, A., Meredith, P., & Sarna, T. (2009) · Angewandte Chemie · doi:10.1002/ange.200803786 · Cited by 44 · see citing works
Self-citationTsubaki, K., Tanaka, H., Takaishi, K., Miura, M., Morikawa, H., Furuta, T., Tanaka, K., Fuji, K., Sasamori, T., Tokitoh, N., et al. (2006) · The Journal of Organic Chemistry · doi:10.1021/jo060974v · Cited by 40 · see citing works
UV‐Dissipation Mechanisms in the Eumelanin Building Block DHICA
Huijser, A., Pezzella, A., Hannestad, J. K., Panzella, L., Napolitano, A., d’Ischia, M., & Sundström, V. (2010) · ChemPhysChem · doi:10.1002/cphc.201000257 · Cited by 39 · see citing works
Self-citationPezzella, A., Crescenzi, O., Natangelo, A., Panzella, L., Napolitano, A., Navaratnam, S., Edge, R., Land, E. J., Barone, V., & d’Ischia, M. (2007) · The Journal of Organic Chemistry · doi:10.1021/jo0615807 · Cited by 39 · see citing works
Self-citationIndole-based macrocycles and oligomers binding anions
Suk, J., Chae, M. K., Kim, N. K., Kim, U., & Jeong, K. (2008) · Pure and Applied Chemistry · doi:10.1351/pac200880030599 · Cited by 39 · see citing works
Possible Oxidative Polymerization Mechanism of 5,6-Dihydroxyindole from ab Initio Calculations
Okuda, H., Wakamatsu, K., Ito, S., & Sota, T. (2008) · The Journal of Physical Chemistry A · doi:10.1021/jp711025m · Cited by 38 · see citing works
Design and Synthesis of Novel Dihydroxyindole-2-Carboxylic Acids as HIV-1 Integrase Inhibitors
Sechi, M., Angotzi, G., Dallocchio, R. N., Dessì, A., Carta, F., Sannia, L., Mariani, A., Fiori, S., Sanchez, T. W., Movsessian, L., et al. (2004) · Antiviral chemistry & chemotherapy · doi:10.1177/095632020401500203 · Cited by 36 · see citing works
Wang, T., & Yan, X. (2010) · Chemistry - A European Journal · doi:10.1002/chem.200903188 · Cited by 35 · see citing works
Manini, P., d’Ischia, M., Milosa, M., & Prota, G. (1998) · The Journal of Organic Chemistry · doi:10.1021/jo980875k · Cited by 34 · see citing works
Self-citationBlack, D. S., Ivory, A. J., & Kumar, N. (1996) · Tetrahedron · doi:10.1016/0040-4020(96)00141-x · Cited by 32 · see citing works
Synthesis of Configurationally Defined Sexi- and Octinaphthalene Derivatives
Fuji, K., Furuta, T., & Tanaka, K. (2000) · Organic Letters · doi:10.1021/ol006843c · Cited by 32 · see citing works
Wang, L., Wei, W., Guo, Y., Xu, J., & Shao, S. (2010) · Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy · doi:10.1016/j.saa.2010.12.004 · Cited by 31 · see citing works
Capelli, L., Manini, P., Pezzella, A., Napolitano, A., & d’Ischia, M. (2009) · The Journal of Organic Chemistry · doi:10.1021/jo901259s · Cited by 28 · see citing works
Self-citationA novel fluoride-sensing scaffold by a peculiar acid-promoted trimerization of 5,6-dihydroxyindole
Panzella, L., Pezzella, A., Arzillo, M., Manini, P., Napolitano, A., & d’Ischia, M. (2009) · Tetrahedron · doi:10.1016/j.tet.2009.01.003 · Cited by 28 · see citing works
Self-citationSulphydryl compounds in melanogenesis
d’Ischia, M., Napolitano, A., & Prota, G. (1987) · Tetrahedron · doi:10.1016/s0040-4020(01)87713-9 · Cited by 27 · see citing works
Self-citationSynthesis and physical properties of 5,6-dihydroxyindole
Murphy, B. P., & Schultz, T. M. (1985) · The Journal of Organic Chemistry · doi:10.1021/jo00215a042 · Cited by 27 · see citing works
Arzillo, M., Pezzella, A., Crescenzi, O., Napolitano, A., Land, E. J., Barone, V., & d’Ischia, M. (2010) · Organic Letters · doi:10.1021/ol101188c · Cited by 27 · see citing works
Self-citationSilvestri, R., Artico, M., Bruno, B., Massa, S., Novellino, E., Greco, G., Me, M., Pani, A., Montis, A. D., & Colla, P. L. (1998) · Antiviral chemistry & chemotherapy · doi:10.1177/095632029800900205 · Cited by 27 · see citing works
Novellino, L., d’Ischia, M., & Prota, G. (1999) · Synthesis · doi:10.1055/s-1999-3469 · Cited by 26 · see citing works
Self-citationPezzella, A., Palma, A., Iadonisi, A., Napolitano, A., & d’Ischia, M. (2007) · Tetrahedron Letters · doi:10.1016/j.tetlet.2007.03.141 · Cited by 24 · see citing works
Self-citationGuo, J., Chintharlapalli, S. R., Lee, S., Cho, S. D., Lei, P., Papineni, S., & Safe, S. H. (2009) · Cancer Chemotherapy and Pharmacology · doi:10.1007/s00280-009-1144-0 · Cited by 24 · see citing works
Expedient routes to valuable bromo-5,6-dimethoxyindole building blocks
Huleatt, P. B., Choo, S. S., Chua, S., & Chai, C. L. L. (2008) · Tetrahedron Letters · doi:10.1016/j.tetlet.2008.06.080 · Cited by 23 · see citing works
Efficient synthesis of 5,6-diacetoxyindole: a stable eumelanin precursor
Murphy, B. P. (1985) · The Journal of Organic Chemistry · doi:10.1021/jo00350a089 · Cited by 22 · see citing works
Reactivity of 3-substituted indolin-2-ones in vilsmeier-type reactions of 4,6-dimethoxyindoles
Black, D. S., Ivory, A. J., & Kumar, N. (1996) · Tetrahedron · doi:10.1016/0040-4020(96)00305-5 · Cited by 20 · see citing works
Pezzella, A., Ambrogi, V., Arzillo, M., Napolitano, A., Carfagna, C., & d’Ischia, M. (2010) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2010.00730.x · Cited by 14 · see citing works
Self-citationCapelli, L., Manini, P., Pezzella, A., & d’Ischia, M. (2010) · Organic & Biomolecular Chemistry · doi:10.1039/c0ob00037j · Cited by 13 · see citing works
Self-citationCardiac-slowing amidines containing the 3-thioindole group. Potential antianginal agents
Zelesko, M. J., McComsey, D. F., Hageman, W., Nortey, S. O., Baker, C. A., & Maryanoff, B. E. (1983) · Journal of Medicinal Chemistry · doi:10.1021/jm00356a021 · Cited by 13 · see citing works
Capelli, L., Crescenzi, O., Manini, P., Pezzella, A., Barone, V., & d’Ischia, M. (2011) · The Journal of Organic Chemistry · doi:10.1021/jo200232t · Cited by 12 · see citing works
Self-citationPorter, J., Arreguin, S., & Pierpont, C. G. (2010) · Inorganica Chimica Acta · doi:10.1016/j.ica.2010.05.011 · Cited by 12 · see citing works
245. Melanin and its precursors. Part I. The synthesis of 5 : 6 : 5′ : 6′-tetrahydroxyindigo
Harley-Mason, J. (1948) · Journal of the Chemical Society (Resumed) · doi:10.1039/jr9480001244 · Cited by 11 · see citing works
The Melanin Problem : a Synthesis of 5 : 6-Dihydroxy-Indole and Its Derivatives
BURTON, H., & DUFFIELD, J. A. (1948) · Nature · doi:10.1038/161725a0 · Cited by 11 · see citing works
Oxidation chemistry of 5,6-dihydroxy-2-methylindole
Napolitano, A., Crescenzi, O., Tsiakas, K., & Prota, G. (1993) · Tetrahedron · doi:10.1016/s0040-4020(01)91231-1 · Cited by 10 · see citing works
Self-citationManini, P., Pezzella, A., Panzella, L., Napolitano, A., & d’Ischia, M. (2005) · Tetrahedron · doi:10.1016/j.tet.2005.02.030 · Cited by 10 · see citing works
Self-citationSechi, M., Casu, F., Campesi, I., Fiori, S., & Mariani, A. (2006) · Molecules · doi:10.3390/11120968 · Cited by 9 · see citing works
The Melanin Problem : a Synthesis of 5 : 6-Dihydroxyindole
Beer, R. J. S., CLARKE, K., Khorana, H. G., & ROBERTSON, A. (1948) · Nature · doi:10.1038/161525a0 · Cited by 8 · see citing works
Okuda, H., Wakamatsu, K., Ito, S., & Sota, T. (2010) · Chemical Physics Letters · doi:10.1016/j.cplett.2010.03.054 · Cited by 6 · see citing works
The first characterisation of a transient 5,6-indolequinone
Napolitano, A., Pezzella, A., d’Ischia, M., & Prota, G. (1996) · Tetrahedron Letters · doi:10.1016/0040-4039(96)00806-4 · Cited by 5 · see citing works
Self-citation
Flagged first, then by citations
Cited by
Sorted by citations
Surface Modification of Water Purification Membranes
Miller, D. J., Dreyer, D. R., Bielawski, C. W., Paul, D. R., & Freeman, B. D. (2016) · Angewandte Chemie International Edition · doi:10.1002/anie.201601509 · Cited by 749 · see citing works
Della Vecchia, N. F., Avolio, R., Alfè, M., Errico, M. E., Napolitano, A., & d'Ischia, M. (2013) · Advanced Functional Materials · doi:10.1002/adfm.201202127 · Cited by 582 · see citing works
Self-citationMelanins and melanogenesis: from pigment cells to human health and technological applications
d’Ischia, M., Wakamatsu, K., Cicoira, F., Mauro, E. D., García-Borrón, J. C., Commo, S., Galván, I., Ghanem, G., Kenzo, K., Meredith, P., et al. (2015) · Pigment Cell & Melanoma Research · doi:10.1111/pcmr.12393 · Cited by 491 · see citing works
Self-citationPerspectives on poly(dopamine)
Dreyer, D. R., Miller, D. J., Freeman, B. D., Paul, D. R., & Bielawski, C. W. (2013) · Chemical Science · doi:10.1039/c3sc51501j · Cited by 378 · see citing works
Quinone and its derivatives for energy harvesting and storage materials
Son, E., Kim, J. H., Kim, K., & Park, C. B. (2016) · Journal of Materials Chemistry A · doi:10.1039/c6ta03123d · Cited by 176 · see citing works
Membranes with Surface-Enhanced Antifouling Properties for Water Purification
Shahkaramipour, N., Tran, T., Ramanan, S. N., & Lin, H. (2017) · Membranes · doi:10.3390/membranes7010013 · Cited by 225 · see citing works
Melanin Biopolymers: Tailoring Chemical Complexity for Materials Design
d’Ischia, M., Napolitano, A., Pezzella, A., Meredith, P., & Buehler, M. J. (2019) · Angewandte Chemie International Edition · doi:10.1002/anie.201914276 · Cited by 191 · see citing works
Self-citationOxidative Self-Polymerization of Dopamine in an Acidic Environment
Zheng, W., Fan, H., Wang, L., & Jin, Z. (2015) · Langmuir · doi:10.1021/acs.langmuir.5b02757 · Cited by 184 · see citing works
Mimicking Melanosomes: Polydopamine Nanoparticles as Artificial Microparasols
Huang, Y., Li, Y., Hu, Z., Yue, X., Proetto, M. T., Jones, Y., & Gianneschi, N. C. (2017) · ACS Central Science · doi:10.1021/acscentsci.6b00230 · Cited by 163 · see citing works
Micillo, R., Panzella, L., Koike, K., Monfrecola, G., Napolitano, A., & D’Ischia, M. (2016) · International Journal of Molecular Sciences · doi:10.3390/ijms17050746 · Cited by 135 · see citing works
Self-citationThe Chemistry of Bioinspired Catechol(amine)-Based Coatings.
Lyu, Q., Hsueh, N., & Chai, C. (2019) · ACS Biomaterials Science & Engineering · doi:10.1021/acsbiomaterials.9b00281 · Cited by 101 · see citing works
Chemistry of polydopamine analogues
Mrówczyński, R., Markiewicz, R., & Liebscher, J. (2016) · Polymer International · doi:10.1002/pi.5193 · Cited by 116 · see citing works
Saraf, M., Prateek, P., Ranjan, R., Balasubramaniam, B., Thakur, V. K., & Gupta, R. K. (2023) · Advanced Materials Interfaces · doi:10.1002/admi.202300670 · Cited by 106 · see citing works
Oberflächenmodifizierung von Wasseraufbereitungsmembranen
Miller, D. J., Dreyer, D. R., Bielawski, C. W., Paul, D. R., & Freeman, B. D. (2016) · Angewandte Chemie · doi:10.1002/ange.201601509 · Cited by 104 · see citing works
Polydopamine Nanoparticles Prepared Using Redox-Active Transition Metals
Salomäki, M., Ouvinen, T., Marttila, L., Kivelä, H., Leiro, J. A., Mäkilä, E. M., & Lukkari, J. (2019) · The Journal of Physical Chemistry B · doi:10.1021/acs.jpcb.8b11994 · Cited by 102 · see citing works
Polydopamine-Assisted Surface Modification for Bone Biosubstitutes
Huang, S., Liang, N., Hu, Y., Zhou, X., & Abidi, N. (2016) · BioMed Research International · doi:10.1155/2016/2389895 · Cited by 97 · see citing works
Sugumaran, M. (2016) · International Journal of Molecular Sciences · doi:10.3390/ijms17091576 · Cited by 94 · see citing works
Polydopamine films and particles with catalytic activity
Ball, V. (2017) · Catalysis Today · doi:10.1016/j.cattod.2017.01.031 · Cited by 81 · see citing works
Covalent Modification and Regulation of the Nuclear Receptor Nurr1 by a Dopamine Metabolite
Bruning, J. M., Wang, Y., Oltrabella, F., Tian, B., Kholodar, S. A., Liu, H., Bhattacharya, P., Guo, S., Holton, J. M., Fletterick, R. J., et al. (2019) · Cell chemical biology · doi:10.1016/j.chembiol.2019.02.002 · Cited by 78 · see citing works
The Late Stages of Melanogenesis: Exploring the Chemical Facets and the Application Opportunities
Panzella, L., Ebato, A., Napolitano, A., & Koike, K. (2018) · International Journal of Molecular Sciences · doi:10.3390/ijms19061753 · Cited by 70 · see citing works
Self-citationPark, H., Yang, K., Kim, M.-J., Jang, J., Lee, M., Kim, D., Lee, H., & Cho, S. (2015) · Biomaterials · doi:10.1016/j.biomaterials.2015.01.015 · Cited by 63 · see citing works
Polydopamine – its Prolific Use as Catalyst and Support Material
Molnár, Á. (2019) · ChemCatChem · doi:10.1002/cctc.201902125 · Cited by 60 · see citing works
A Perspective on the Ultrafast Photochemistry of Solution-Phase Sunscreen Molecules
Baker, L. A., Greenough, S. E., & Stavros, V. G. (2016) · The Journal of Physical Chemistry Letters · doi:10.1021/acs.jpclett.6b02104 · Cited by 57 · see citing works
Multifunctional coatings hinging on the catechol/amine interplay
Alfieri, M. L., Panzella, L., & Napolitano, A. (2023) · European Journal of Organic Chemistry · doi:10.1002/ejoc.202301002 · Cited by 51 · see citing works
Self-citationBall, V. (2014) · Biointerphases · doi:10.1116/1.4875115 · Cited by 45 · see citing works
Tuna, D., Udvarhelyi, A., Sobolewski, A. L., Domcke, W., & Domratcheva, T. M. (2016) · The Journal of Physical Chemistry B · doi:10.1021/acs.jpcb.6b01793 · Cited by 43 · see citing works
Corani, A., Huijser, A., Iadonisi, A., Pezzella, A., Sundström, V., & d’Ischia, M. (2012) · The Journal of Physical Chemistry B · doi:10.1021/jp306436f · Cited by 42 · see citing works
Self-citationIn Situ Formation of Dendrites in Eumelanin Thin Films between Gold Electrodes
Wünsche, J., Cardenas, L., Rosei, F., Cicoira, F., Gauvin, R., Graeff, C. F. O., Poulin, S., Pezzella, A., & Santato, C. (2013) · Advanced Functional Materials · doi:10.1002/adfm.201300715 · Cited by 41 · see citing works
Self-citationIndole-5,6-quinones display hallmark properties of eumelanin
Wang, X., Kinziabulatova, L., Bortoli, M., Manickoth, A., Barilla, M. A., Huang, H., Blancafort, L., Kohler, B., & Lumb, J. (2023) · Nature Chemistry · doi:10.1038/s41557-023-01175-4 · Cited by 40 · see citing works
Nogueira, J. J., Corani, A., El Nahhas, A., Pezzella, A., d’Ischia, M., González, L., & Sundström, V. (2017) · The Journal of Physical Chemistry Letters · doi:10.1021/acs.jpclett.6b03012 · Cited by 39 · see citing works
Self-citationEumelanin-inspired nanomaterials in electrochemical energy storage devices: A review
Pan, J., Xia, Z., Deng, N., Chen, L., Zhang, H., Lu, Y., Liu, Y., & Gao, H. (2022) · Chemical Engineering Journal · doi:10.1016/j.cej.2022.138607 · Cited by 37 · see citing works
Fan, K. W., Roberts, J. J., Martens, P. J., Stenzel, M. H., & Granville, A. M. (2015) · Journal of Materials Chemistry B · doi:10.1039/c5tb01150g · Cited by 35 · see citing works
Nonenzymatic Spontaneous Oxidative Transformation of 5,6-Dihydroxyindole
Sugumaran, M., Evans, J. J., Ito, S., & Wakamatsu, K. (2020) · International Journal of Molecular Sciences · doi:10.3390/ijms21197321 · Cited by 32 · see citing works
The modulation of melanin‐like materials: methods, characterization and applications
Jin, Z., & Fan, H. (2016) · Polymer International · doi:10.1002/pi.5187 · Cited by 31 · see citing works
Degree of polymerization of 5,6‐dihydroxyindole‐derived eumelanin from chemical degradation study
Okuda, H., Yoshino, K., Wakamatsu, K., Ito, S., & Sota, T. (2014) · Pigment Cell & Melanoma Research · doi:10.1111/pcmr.12254 · Cited by 28 · see citing works
Photovoltaic properties of PSi impregnated with eumelanin
Mula, G., Manca, L., Setzu, S., & Pezzella, A. (2012) · Nanoscale Research Letters · doi:10.1186/1556-276x-7-377 · Cited by 27 · see citing works
Self-citationKholodar, S. A., Lang, G., Cortopassi, W. A., Iizuka, Y., Brah, H., Jacobson, M. P., & England, P. M. (2021) · ACS Chemical Biology · doi:10.1021/acschembio.1c00326 · Cited by 26 · see citing works
Vinod, K., Mathew, R., Jandl, C., Thomas, B., & Hariharan, M. (2024) · Chemical Science · doi:10.1039/d4sc05453a · Cited by 25 · see citing works
Wakamatsu, K., Nakao, K., Tanaka, H., Kitahori, Y., Tanaka, Y., Ojika, M., & Ito, S. (2019) · International Journal of Molecular Sciences · doi:10.3390/ijms20102575 · Cited by 22 · see citing works
Adinolfi, M., d’Ischia, M., Iadonisi, A., Leone, L., Pezzella, A., & Valerio, S. (2012) · European Journal of Organic Chemistry · doi:10.1002/ejoc.201200299 · Cited by 20 · see citing works
Self-citationIto, S., Napolitano, A., Sarna, T., & Wakamatsu, K. (2022) · Journal of Neural Transmission · doi:10.1007/s00702-022-02574-6 · Cited by 18 · see citing works
Self-citationNature-inspired safe and efficient hair dyes: beyond the traditional hair dyes
Zhang, T., Hu, J., Guo, L., Gu, Z., Jiang, X. L., & Li, Y. (2024) · Green Chemistry · doi:10.1039/d3gc04741e · Cited by 18 · see citing works
From melanogenesis to melanin technologies
Al‐Shamery, N., Biyashev, D., Blancafort, L., Camus, A., Gianneschi, N. C., Graeff, C. F. O., Kohler, B., Li, S., Lu, K. Q., Lumb, J., et al. (2025) · Communications Chemistry · doi:10.1038/s42004-025-01731-8 · Cited by 17 · see citing works
Melanin Biopolymers: Tailoring Chemical Complexity for Materials Design
d’Ischia, M., Napolitano, A., Pezzella, A., Meredith, P., & Buehler, M. J. (2019) · Angewandte Chemie · doi:10.1002/ange.201914276 · Cited by 15 · see citing works
Self-citationMelanin‐Inspired Organic Electronics: Electroluminescence in Asymmetric Triazatruxenes
Manini, P., Criscuolo, V., Ricciotti, L., Pezzella, A., Barra, M., Cassinese, A., Crescenzi, O., Maglione, M. G., Tassini, P., Minarini, C., et al. (2015) · ChemPlusChem · doi:10.1002/cplu.201402444 · Cited by 15 · see citing works
Self-citationIacomino, M., Mancebo‐Aracil, J., Guardingo, M., Martín, R., D’Errico, G., Perfetti, M., Manini, P., Crescenzi, O., Busquè, F., Napolitano, A., et al. (2017) · International Journal of Molecular Sciences · doi:10.3390/ijms18102169 · Cited by 15 · see citing works
Self-citationFan, K. W., Peterson, M. B., Ellersdorfer, P., & Granville, A. M. (2016) · RSC Advances · doi:10.1039/c5ra25590b · Cited by 13 · see citing works
Jarenmark, M., Sjövall, P., Ito, S., Wakamatsu, K., & Lindgren, J. (2020) · International Journal of Molecular Sciences · doi:10.3390/ijms22010161 · Cited by 12 · see citing works
Kopeć, K., Ryżko, A., Major, R., Plutecka, H., Więcek, J., Pikus, G., Trzciński, J., Kalinowska, A., & Ciach, T. (2022) · ACS Omega · doi:10.1021/acsomega.2c05289 · Cited by 12 · see citing works
Marchi, F. D., Galeotti, G., Šimėnas, M., Ji, P., Chi, L., Tornau, E. E., Pezzella, A., Macleod, J. M., Ebrahimi, M., & Rosei, F. (2019) · Nanoscale · doi:10.1039/c8nr09810g · Cited by 12 · see citing works
Self-citationPezzella, A., & Wünsche, J. (2013) · Organic Electronics · doi:10.1002/9783527650965.ch05 · Cited by 7 · see citing works
Self-citationViggiano, S., Alfieri, M. L., Panzella, L., Crescenzi, O., & Napolitano, A. (2024) · Bioorganic Chemistry · doi:10.1016/j.bioorg.2024.107928 · Cited by 5 · see citing works
Self-citationHuang, H., Kinziabulatova, L., Manickoth, A., Zhang, Y., Barilla, M. A., Blancafort, L., Kohler, B., & Lumb, J. (2025) · Chemical Science · doi:10.1039/d4sc08610d · Cited by 5 · see citing works
Adhikari, S., Essandoh, M. A., Starr, W. C., Sah, P., Force, C. N. L., Eleshy, R., Lutter, E. I., & Nelson, T. L. (2022) · ACS Applied Bio Materials · doi:10.1021/acsabm.1c01036 · Cited by 5 · see citing works
Salinger, M. T., Garrido, D. C., Lamming, E. D., Ward, J. M., Moody, T. S., Jeffries, J. W. E., & Hailes, H. C. (2024) · ChemCatChem · doi:10.1002/cctc.202400492 · Cited by 5 · see citing works
Synthesis and Liquid Crystalline Self‐Assembly of Concave Diindoles with a Hydropentalene Core
Bühlmeyer, A., Ehni, P., Ullmann, D., Frey, W. U., Baro, A., & Laschat, S. (2021) · European Journal of Organic Chemistry · doi:10.1002/ejoc.202001656 · Cited by 4 · see citing works
Caputo, G., Bonadies, I., Migliaccio, L., Caso, M. F., & Pezzella, A. (2018) · Materials · doi:10.3390/ma11091494 · Cited by 2 · see citing works
Self-citationHockey-stick indoles: turning a calamitic neutral mesogen into an ionic liquid crystal
Trübe, K., Bühlmeyer, A., Schulz, F., Grunwald, M. A., Zens, A., Baro, A., & Laschat, S. (2021) · Liquid Crystals · doi:10.1080/02678292.2021.1951382 · Cited by 1 · see citing works
Kosmetikindustrie: Henna und Heteroaromatisches
Hartmann, H., & Pratt, D. M. (2022) · Nachrichten aus der Chemie · doi:10.1002/nadc.20224121433
Banaś, K. D., Mokrzynski, K. T., & Plonka, P. M. (2026) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/j.jphotobiol.2026.113533
5,6-Dihydroxyindole thin films for biocompatible charge transport modulation in organic blends
Ahmad, J., Carrella, E., Jhang, B.-C., Traboni, S., Aydınoğlu, S., Capasso, D., Capua, R. D., & Pezzella, A. (2026) · Materials Chemistry and Physics · doi:10.1016/j.matchemphys.2026.133004
Self-citation
- Authors
- d'Ischia, M., Napolitano, A., & Pezzella, A.
- Affiliations
- University of Naples Federico II (IT)
- Venue
- European Journal of Organic Chemistry
- Publisher
- Wiley
- Published
- 2011-09-02
- Volume
- 2011
- Issue
- 28
- Pages
- 5501-5516
- ISSN
- 1099-0690 (ISSN-L)
- 1434-193X
- OpenAlex
- W2141923410
- Cited by
- 62
- References
- 83
- Citations by year
- 2026: 3 · 2025: 2 · 2024: 4 · 2023: 3 · 2022: 5 · 2021: 3 · 2020: 2 · 2019: 8 · 2018: 2 · 2017: 5 · 2016: 11 · 2015: 5 · 2014: 2 · 2013: 3 · 2012: 4
- FWCI
- 1.35
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- European Journal of Organic Chemistry (publishedVersion)
- Scuola Normale Superiore di Pisa (submittedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Properties of Aromatic Compounds
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis of Indole Derivatives
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cell Biology › melanin and skin pigmentation
- Keywords
- 5,6-dihydroxyindole, eumelanin, biomimetic polymers, nanomaterials, π-electron systems, photophysical properties, organic synthesis, molecular design, optoelectronic properties
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