Chemistry:4-Deoxypyridoxine
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| Preferred IUPAC name
5-(Hydroxymethyl)-2,4-dimethylpyridin-3-ol | |
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3D model (JSmol)
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| Properties | |
| C8H11NO2 | |
| Molar mass | 153.181 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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4-Deoxypyridoxine is a vitamin B6 antagonist.[1] It may be toxic to developing embryos since it can have negative effects on collagen and elastin during development.[2] The presence of this compound can produce vitamin B6 deficiency, which suppresses the immune system.[3] 4-Deoxypyridoxine lowers vitamin B6 concentration by competitively inhibiting some of the enzymes necessary for the regeneration of vitamin B6.[4] The related immunosuppression can be beneficial in animal models of Trichinella spiralis infections.[5] 4-Deoxypyridoxine has also been described as an inhibitor of sphingosine-1-phosphate lyase.[6] The inhibition of sphingosine-1-phosphate lyase by 4-Deoxypyridoxine has been shown to prevent cell death of ex-vivo animal pancreatic islets. The use of 4-Deoxypyridoxine to prevent stress-induced apoptosis is suggest that the compound, as well as other inhibitors of sphingosine-1-phosphate lyase, could be used to increase the viability of donor pancreatic tissue in the treatment of diabetes.[7]
References
- ↑ "Effects of vitamin B-6 deficiency and 4'- deoxypyridoxine on pyridoxal phosphate concentrations, pyridoxine kinase and other aspects of metabolism in the rat". J. Nutr. 111 (2): 391–8. 1 February 1981. doi:10.1093/jn/111.2.391. PMID 6257871.
- ↑ "The effect of a vitamin B-6 antagonist, 4-deoxypyridoxine, on the cross-linking of collagen in the developing chick embryo". Biochem. J. 210 (3): 633–8. 1983. doi:10.1042/bj2100633. PMID 6135414.
- ↑ "Effect of pyridoxine deficiency on immunological phenomena". Postgrad Med J 68 (Suppl 1): S70–7. 1992. PMID 1409221.
- ↑ Sheridan, E.; Gillespie, S.; Johnson, C. R.; Lecavalier, L.; Smith, T.; Swiezy, N.; Turner, K.; Pritchett, J. et al. (2021). "Using Parent Target Problem Narratives to Evaluate Outcomes in Children with Autism Spectrum Disorder". Research on Child and Adolescent Psychopathology 49 (11): 1527–1535. doi:10.1007/s10802-021-00843-8. PMID 34213717.
- ↑ "Vitamin B6-deficient diet plus 4-deoxypyridoxine (4-DPD) reduces the inflammatory response induced by T. spiralis in diaphragm, masseter and heart muscle tissue of mice". Mol. Cell. Biochem. 197 (1–2): 79–85. 1999. doi:10.1023/A:1006958310081. PMID 10485327.
- ↑ Weigel, Cynthia; Hüttner, Sören S.; Ludwig, Kristin; Krieg, Nadine; Hofmann, Susann; Schröder, Nathalie H.; Robbe, Linda; Kluge, Stefan et al. (2020-08-01). "S1P lyase inhibition protects against sepsis by promoting disease tolerance via the S1P/S1PR3 axis" (in English). eBioMedicine 58: 102898. doi:10.1016/j.ebiom.2020.102898. ISSN 2352-3964. PMID 32711251.
- ↑ Lee, Hakmo; Seon Park, Ho; Hee Hong, Shin; Kyung Choi, Ok; Cho, Sung-Dae; Park, Jongwoo; Eun Oh, Ju; Soo Chung, Sung et al. (2013). "4-deoxypyridoxine improves the viability of isolated pancreatic islets ex vivo". Islets 5 (3): 116–121. doi:10.4161/isl.25254. PMID 23756681.
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