Synthesis and chemical composition analysis of protocatechualdehyde-based novel melanin dye by 15T FT-ICR: High dyeing performance on soft contact lens
Source abstract
Abstract
Abstract In this study, novel melanin pigments were prepared through the eco-friendly microbial conversion of caffeic acid by engineering Escherichia coli BL21(DE3) cells. The cells expressed feruloyl-CoA synthetase (FCS) and enoyl-CoA hydratase/aldolase (ECH) for the conversion of caffeic acid into protocatechualdehyde. The synthesized protocatechualdehyde further underwent oxidative modification into a diquinone structure, followed by polymerization into melanin complex (F/E-Melanin). The expression of FCS and ECH in the presence of 90 mg/L caffeic acid (0.5 mM) could produce F/E-Melanin black pigments up to 170 mg dry wt/L within 12 h. Interestingly, the synthesized melanin was applied for hydrogel of soft contact lens dyeing and showed excellent dyeing performance with biological activities of antibacterial and antioxidant capacities, as well as a higher water-content rate than those of the existing synthetic melanins prepared in this study. The synthesized F/E-Melanin polymers were structurally analyzed by 1H NMR and FT-IR. Interestingly, the molecular composition such as Van Krevelen plots with H/C and O/C ratio, double bond equivalents with carbon number, and CHONS distribution of the five synthetic melanins were characterized by interpreting data obtained from 15T FT-ICR mass spectrometry analysis.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: melanin and skin pigmentation · Dyeing and Modifying Textile Fibers · Skin Protection and Aging
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (25)
Show source-provided references
1. Quantitative analysis of eumelanin and pheomelanin in humans, mice, and other animals: a comparative review10.1034/j.1600-0749.2003.00072.x ↗
2. FCS and ECH dependent production of phenolic aldehyde and melanin pigment from l-tyrosine in Escherichia coli10.1016/j.enzmictec.2017.10.011 ↗
3. From tyrosine to melanin: signaling pathways and factors regulating melanogenesis10.5604/17322693.1208033 ↗
4. Analysis of melanin-like pigment synthesized from homogentisic acid, with or without tyrosine, and its implications in alkaptonuria
5. A novel UV-shielding and transparent polymer film: when bioinspired dopamine-melanin hollow nanoparticles join polymers10.1021/acsami.7b08763 ↗
6. Determination of wavelength-specific UV protection factors of sunscreens in intact skin by EPR measurement of UV-induced reactive melanin radical10.1111/j.1751-1097.2007.00089.x ↗
7. Antimicrobial activity of eumelanin-based hybrids: the role of TiO2 in modulating the structure and biological performance10.1016/j.msec.2016.12.135 ↗
8. Melanin nanoparticles derived from a homology of medicine and food for sentinel lymph node mapping and photothermal in vivo cancer therapy10.1016/j.biomaterials.2016.03.018 ↗
9. Comprehensive insights into the multi-antioxidative mechanisms of melanin nanoparticles and their application to protect brain from injury in ischemic stroke10.1021/jacs.6b11013 ↗
10. Photoprotection of bacterial-derived melanin against ultraviolet A-induced cell death and its potential application as an active sunscreen10.1111/j.1468-3083.2007.02574.x ↗
11. Biosynthesis of catechol melanin from glycerol employing metabolically engineered Escherichia coli10.1186/s12934-016-0561-0 ↗
12. Metabolic engineering of Escherichia coli to optimize melanin synthesis from glucose10.1186/1475-2859-12-108 ↗
13. Melanin from the nitrogen-fixing bacterium Azotobacter chroococcum: a spectroscopic characterization10.1371/journal.pone.0084574 ↗
14. Bioproduction, characterization, anticancer and antioxidant activities of extracellular melanin pigment produced by newly isolated microbial cell factories Streptomyces glaucescens NEAE-H10.1038/srep42129 ↗
15. Using tyrosinase as a monophenol monooxygenase: a combined strategy for effective inhibition of melanin formation10.1002/bit.25855 ↗
16. Chemical characterization of dissolved organic matter in moist acidic tussock tundra soil using ultra-high resolution 15T FT-ICR mass spectrometry10.1007/s12257-017-0121-4 ↗
17. Water-soluble atmospheric organic matter in fog: exact masses and chemical formula identification by ultrahigh-resolution fourier transform ion cyclotron resonance mass spectrometry10.1021/es903409k ↗
18. Molecular formulae of marine and terrigenous dissolved organic matter detected by electrospray ionization fourier transform ion cyclotron resonance mass spectrometry10.1016/j.gca.2005.02.027 ↗
19. Graphical method for analysis of ultrahigh-resolution broadband mass spectra of natural organic matter, the van Krevelen diagram10.1021/ac034415p ↗
20. Production of natural melanin by Auricularia auricula and study on its molecular structure10.1016/j.foodchem.2015.06.042 ↗
21. NMR studies of melanins: characterization of a soluble melanin free acid from Sepia ink10.1111/j.1600-0749.1991.tb00443.x ↗
22. [Study on melanin from taihe silky fowl and its complexes with Cu2+, Fe3+ ions by IR spectrum]
23. Interactive van Krevelen diagrams - advanced visualisation of mass spectrometry data of complex mixtures10.1002/rcm.7823 ↗
24. Wu · Anal Chem · 2004 · 76 · 251110.1021/ac0355449 ↗
25. Characterization and quantitation of PVP content in a silicone hydrogel contact lens produced by dual-phase polymerization processing10.1002/jbm.b.33904 ↗