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4-Deoxypyridoxine

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4-Deoxypyridoxine
4-Deoxypyridoxine
Names
Preferred IUPAC name 5-(Hydroxymethyl)-2,4-dimethylpyridin-3-ol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H11NO2/c1-5-7(4-10)3-9-6(2)8(5)11/h3,10-11H,4H2,1-2H3Key: KKOWAYISKWGDBG-UHFFFAOYSA-N
  • InChI=1/C8H11NO2/c1-5-7(4-10)3-9-6(2)8(5)11/h3,10-11H,4H2,1-2H3Key: KKOWAYISKWGDBG-UHFFFAOYAH
SMILES
  • CC1=C(C(=NC=C1CO)C)O
  • Oc1c(c(cnc1C)CO)C
Properties
Chemical formula C8H11NO2
Molar mass 153.181 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

4-Deoxypyridoxine is a vitamin B6 antagonist. It may be toxic to developing embryos since it can have negative effects on collagen and elastin during development. The presence of this compound can produce vitamin B6 deficiency, which suppresses the immune system. 4-Deoxypyridoxine lowers vitamin B6 concentration by competitively inhibiting some of the enzymes necessary for the regeneration of vitamin B6. The related immunosuppression can be beneficial in animal models of Trichinella spiralis infections. 4-Deoxypyridoxine has also been described as an inhibitor of sphingosine-1-phosphate lyase. 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.

References

  1. Coburn SP, Mahuren JD, Schaltenbrand WE, Wostmann BS, Madsen D (1 February 1981). "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. doi:10.1093/jn/111.2.391. PMID 6257871.
  2. Bird TA, Levene CI (1983). "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. doi:10.1042/bj2100633. PMC 1154271. PMID 6135414.
  3. Trakatellis A, Dimitriadou A, Exindari M, et al. (1992). "Effect of pyridoxine deficiency on immunological phenomena". Postgrad Med J. 68 (Suppl 1): S70–7. PMID 1409221.
  4. Sheridan, E.; Gillespie, S.; Johnson, C. R.; Lecavalier, L.; Smith, T.; Swiezy, N.; Turner, K.; Pritchett, J.; Mruzek, D. W.; Evans, A. N.; Bearss, K.; Scahill, L. (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. S2CID 235709478.
  5. Frydas S, Papaioanou N, Vlemmas I, et al. (1999). "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. doi:10.1023/A:1006958310081. PMID 10485327. S2CID 23457740.
  6. Weigel, Cynthia; Hüttner, Sören S.; Ludwig, Kristin; Krieg, Nadine; Hofmann, Susann; Schröder, Nathalie H.; Robbe, Linda; Kluge, Stefan; Nierhaus, Axel; Winkler, Martin S.; Rubio, Ignacio (2020-08-01). "S1P lyase inhibition protects against sepsis by promoting disease tolerance via the S1P/S1PR3 axis". eBioMedicine. 58: 102898. doi:10.1016/j.ebiom.2020.102898. ISSN 2352-3964. PMC 7381498. PMID 32711251.
  7. Lee, Hakmo; Seon Park, Ho; Hee Hong, Shin; Kyung Choi, Ok; Cho, Sung-Dae; Park, Jongwoo; Eun Oh, Ju; Soo Chung, Sung; Jung, Hye Seung; Park, Kyong Soo (2013). "4-deoxypyridoxine improves the viability of isolated pancreatic islets ex vivo". Islets. 5 (3): 116–121. doi:10.4161/isl.25254. PMID 23756681. S2CID 22959354.

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