Catecholamine Derivatives as Novel Crosslinkers for the Synthesis of Versatile Biopolymers
Catecholamine metabolites are not only involved in primary metabolism, but also in secondary metabolism, serving a diverse array of physiologically and biochemically important functions. Melanin, which originates from dopa and dopamine, found in the hair, eye, and skin of all animals, is an importan...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-09-01
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| Series: | Journal of Functional Biomaterials |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2079-4983/14/9/449 |
| _version_ | 1797579427159212032 |
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| author | Manickam Sugumaran Jason J. Evans |
| author_facet | Manickam Sugumaran Jason J. Evans |
| author_sort | Manickam Sugumaran |
| collection | DOAJ |
| description | Catecholamine metabolites are not only involved in primary metabolism, but also in secondary metabolism, serving a diverse array of physiologically and biochemically important functions. Melanin, which originates from dopa and dopamine, found in the hair, eye, and skin of all animals, is an important biopolymeric pigment. It provides protection against damaging solar radiation to animals. N-Acetyldopamine and N-β-alanyldopamine play a crucial role in the hardening of the exoskeletons of all insects. In addition, insects and other arthropods utilize the melanogenic process as a key component of their defense systems. Many marine organisms utilize dopyl peptides and proteins as bonding materials to adhere to various substrata. Moreover, the complex dopa derivatives that are precursors to the formation of the exoskeletons of numerous marine organisms also exhibit antibiotic properties. The biochemistry and mechanistic transformations of different catecholamine derivatives to produce various biomaterials with antioxidant, antibiotic, crosslinking, and gluing capabilities are highlighted. These reactivities are exhibited through the transient and highly reactive quinones, quinone methides, and quinone methide imine amide intermediates, as well as chelation to metal ions. A careful consideration of the reactivities summarized in this review will inspire numerous strategies for synthesizing novel biomaterials for future medical and industrial use. |
| first_indexed | 2024-03-10T22:36:05Z |
| format | Article |
| id | doaj.art-3aadd2a8ec63466baf350f68a86d6b00 |
| institution | Directory Open Access Journal |
| issn | 2079-4983 |
| language | English |
| last_indexed | 2024-03-10T22:36:05Z |
| publishDate | 2023-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Journal of Functional Biomaterials |
| spelling | doaj.art-3aadd2a8ec63466baf350f68a86d6b002023-11-19T11:23:14ZengMDPI AGJournal of Functional Biomaterials2079-49832023-09-0114944910.3390/jfb14090449Catecholamine Derivatives as Novel Crosslinkers for the Synthesis of Versatile BiopolymersManickam Sugumaran0Jason J. Evans1Department of Biology, University of Massachusetts Boston, Boston, MA 02125, USADepartment of Chemistry, University of Massachusetts Boston, Boston, MA 02125, USACatecholamine metabolites are not only involved in primary metabolism, but also in secondary metabolism, serving a diverse array of physiologically and biochemically important functions. Melanin, which originates from dopa and dopamine, found in the hair, eye, and skin of all animals, is an important biopolymeric pigment. It provides protection against damaging solar radiation to animals. N-Acetyldopamine and N-β-alanyldopamine play a crucial role in the hardening of the exoskeletons of all insects. In addition, insects and other arthropods utilize the melanogenic process as a key component of their defense systems. Many marine organisms utilize dopyl peptides and proteins as bonding materials to adhere to various substrata. Moreover, the complex dopa derivatives that are precursors to the formation of the exoskeletons of numerous marine organisms also exhibit antibiotic properties. The biochemistry and mechanistic transformations of different catecholamine derivatives to produce various biomaterials with antioxidant, antibiotic, crosslinking, and gluing capabilities are highlighted. These reactivities are exhibited through the transient and highly reactive quinones, quinone methides, and quinone methide imine amide intermediates, as well as chelation to metal ions. A careful consideration of the reactivities summarized in this review will inspire numerous strategies for synthesizing novel biomaterials for future medical and industrial use.https://www.mdpi.com/2079-4983/14/9/449dopadopamineN-acyldopaminestunichromesdopyl proteinssclerotization |
| spellingShingle | Manickam Sugumaran Jason J. Evans Catecholamine Derivatives as Novel Crosslinkers for the Synthesis of Versatile Biopolymers Journal of Functional Biomaterials dopa dopamine N-acyldopamines tunichromes dopyl proteins sclerotization |
| title | Catecholamine Derivatives as Novel Crosslinkers for the Synthesis of Versatile Biopolymers |
| title_full | Catecholamine Derivatives as Novel Crosslinkers for the Synthesis of Versatile Biopolymers |
| title_fullStr | Catecholamine Derivatives as Novel Crosslinkers for the Synthesis of Versatile Biopolymers |
| title_full_unstemmed | Catecholamine Derivatives as Novel Crosslinkers for the Synthesis of Versatile Biopolymers |
| title_short | Catecholamine Derivatives as Novel Crosslinkers for the Synthesis of Versatile Biopolymers |
| title_sort | catecholamine derivatives as novel crosslinkers for the synthesis of versatile biopolymers |
| topic | dopa dopamine N-acyldopamines tunichromes dopyl proteins sclerotization |
| url | https://www.mdpi.com/2079-4983/14/9/449 |
| work_keys_str_mv | AT manickamsugumaran catecholaminederivativesasnovelcrosslinkersforthesynthesisofversatilebiopolymers AT jasonjevans catecholaminederivativesasnovelcrosslinkersforthesynthesisofversatilebiopolymers |