The DOI matches its Crossref record; 107 of the 107 references it cites were found in a registry or an index.
Kynuramines, metabolites of melatonin and other indoles: the resurrection of an almost forgotten class of biogenic amines
Abstract
Abstract: Kynuramines represent their own class of biogenic amines. They are formed either by decarboxylation of kynurenines or pyrrole ring cleavage of indoleamines.N2‐formylated compounds formed in this last reaction can be deformylated either enzymatically by arylamine formamidases or hemoperoxidases, or photochemically. The earlier literature mainly focussed on cardiovascular effects of kynuramine, 5‐hydroxykynuramine and their N1,N1‐dimethylated analogs, including indirect effects via release of catecholamines or acetylcholine and interference with serotonin receptors. After the discovery of N1‐acetyl‐N2‐formyl‐5‐methoxykynuramine (AFMK) and N1‐acetyl‐5‐methoxykynuramine (AMK) as major brain metabolites of melatonin, these compounds became of particular interest. They were shown to be produced enzymatically, pseudoenzymatically, by various free radical‐mediated and via photochemical processes. In recent years, AFMK and AMK were shown to scavenge reactive oxygen and nitrogen species, thereby forming several newly discovered 3‐indolinone, cinnolinone and quinazoline compounds, and to protect tissues from damage by reactive intermediates in various models. AMK is of special interest due to its properties as a potent cyclooxygenase inhibitor, NO scavenger forming a stable nitrosation product, inhibitor and/or downregulator of neuronal and inducible NO synthases, and a mitochondrial metabolism modulator. AMK easily interacts with aromates, forms adducts with tyrosyl and tryptophanyl residues, and may modify proteins.
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Cites
Melatonin : a potent, endogenous hydroxyl radical scavenger
Tan, D. (1993) · Endocrine Journal · Cited by 1,659
Self-citationTan, D., Manchester, L. C., Terron, M. P., Flores, L. J., & Reiter, R. J. (2007) · Journal of Pineal Research · doi:10.1111/j.1600-079x.2006.00407.x · Cited by 1,601
Self-citationTan, D.-X., Reiter, R., Manchester, L., Yan, M.-T., El-Sawi, M., Sainz, R., Mayo, J., Kohen, R., Allegra, M., & Hardelan, R. (2002) · Current Topics in Medicinal Chemistry · doi:10.2174/1568026023394443 · Cited by 1,065
Self-citationRelationship between interferon‐γ, indoleamine 2,3‐dioxygenase, and tryptophan catabolism
Taylor, M. W., & Feng, G. (1991) · The FASEB Journal · doi:10.1096/fasebj.5.11.1907934 · Cited by 1,060
Melatonin: Nature’s most versatile biological signal?
Pandi‐Perumal, S. R., Srinivasan, V., Maestroni, G. J. M., Cardinali, D. P., Poeggeler, B., & Hardeland, R. (2006) · The FEBS Journal · doi:10.1111/j.1742-4658.2006.05322.x · Cited by 875
Self-citationHardeland, R. (2005) · Endocrine · doi:10.1385/endo:27:2:119 · Cited by 671
Self-citationREVIEW: Gastrointestinal Melatonin: Localization, Function, and Clinical Relevance
Bubenik, G. A. (2002) · Digestive Diseases and Sciences · doi:10.1023/a:1020107915919 · Cited by 655
Significance of Melatonin in Antioxidative Defense System: Reactions and Products
Tan, D.-X., Manchester, L. C., Reiter, R. J., Qi, W.-B., Karbownik, M., & Calvo, J. R. (2000) · Neurosignals · doi:10.1159/000014635 · Cited by 565
Self-citationHardeland, R., Reiter, R. J., Poeggeler, B., & Tan, D.-X. (1993) · Neuroscience & Biobehavioral Reviews · doi:10.1016/s0149-7634(05)80016-8 · Cited by 424
Self-citationHardeland, R., & Poeggeler, B. (2003) · Journal of Pineal Research · doi:10.1034/j.1600-079x.2003.00040.x · Cited by 398
Self-citation
Cited by
Melatonin—A pleiotropic, orchestrating regulator molecule
Hardeland, R., Cardinali, D. P., Srinivasan, V., Spence, D. W., Brown, G. M., & Pandi-Perumal, S. R. (2011) · Progress in Neurobiology · doi:10.1016/j.pneurobio.2010.12.004 · Cited by 843
Self-citationMelatonin as a Potent and Inducible Endogenous Antioxidant: Synthesis and Metabolism
Tan, D.-X., Manchester, L., Esteban-Zubero, E., Zhou, Z., & Reiter, R. (2015) · Molecules · doi:10.3390/molecules201018886 · Cited by 719
Self-citationMelatonin Synthesis and Function: Evolutionary History in Animals and Plants
Zhao, D., Yu, Y., Shen, Y., Liu, Q., Zhao, Z., Sharma, R., & Reiter, R. J. (2019) · Frontiers in Endocrinology · doi:10.3389/fendo.2019.00249 · Cited by 689
Self-citationMelatonin: A master regulator of plant development and stress responses
Sun, C., Liu, L., Wang, L., Li, B., Jin, C., & Lin, X. (2021) · Journal of Integrative Plant Biology · doi:10.1111/jipb.12993 · Cited by 494
Slominski (2012) · doi:10.1007/978-3-642-19683-6_1 · Cited by 461
Metadata
- Authors
- Hardeland, R., Tan, D., & Reiter, R. J.
- Venue
- Journal of Pineal Research
- Publisher
- Wiley
- Published
- 2009-08-02
- Volume
- 47
- Issue
- 2
- Pages
- 109-126
- ISSN
- 0742-3098 (ISSN-L)
- 1600-079X
- OpenAlex
- W1988934115
- Cited by
- 472
- References
- 107
- FWCI
- 17.61
- Type
- journal article
- Language
- en
- Open access
- closed
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- Hardeland, R., Tan, D., & Reiter, R. J. (2009). Kynuramines, metabolites of melatonin and other indoles: the resurrection of an almost forgotten class of biogenic amines. Journal of Pineal Research. https://doi.org/10.1111/j.1600-079x.2009.00701.x
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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