4-Deoxypyridoxine

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4-Deoxypyridoxine
4-Deoxypyridoxine 4-Deoxypyridoxine.png
4-Deoxypyridoxine
Names
Preferred IUPAC name
5-(Hydroxymethyl)-2,4-dimethylpyridin-3-ol
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C8H11NO2/c1-5-7(4-10)3-9-6(2)8(5)11/h3,10-11H,4H2,1-2H3 Yes check.svgY
    Key: KKOWAYISKWGDBG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H11NO2/c1-5-7(4-10)3-9-6(2)8(5)11/h3,10-11H,4H2,1-2H3
    Key: KKOWAYISKWGDBG-UHFFFAOYAH
  • CC1=C(C(=NC=C1CO)C)O
  • Oc1c(c(cnc1C)CO)C
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

  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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