Pyridoxyl phosphate
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MedKoo CAT#: 529501

CAS#: 54-47-7

Description: Pyridoxyl phosphate is a purinergic P2 receptor antagonist potentially for the treatment of tardive dyskinesia

Chemical Structure

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Pyridoxyl phosphate
CAS# 54-47-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 529501
Name: Pyridoxyl phosphate
CAS#: 54-47-7
Chemical Formula: C8H10NO6P
Exact Mass: 247.02
Molecular Weight: 247.140
Elemental Analysis: C, 38.88; H, 4.08; N, 5.67; O, 38.84; P, 12.53

Price and Availability

Size Price Availability Quantity
5g USD 250
25g USD 450 2 Weeks
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Synonym: MC-1; MC1; MC 1

IUPAC/Chemical Name: (4-formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate

InChi Key: NGVDGCNFYWLIFO-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)

SMILES Code: O=CC1=C(O)C(C)=NC=C1COP(O)(O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Pyridoxal phosphate acts as a coenzyme in all transamination reactions, and in certain decarboxylation, deamination, and racemization reactions of amino acids.
In vitro activity: This study investigated the ability of pyridoxal phosphate to inhibit bifunctional DNA repair glycosylases. Pyridoxal phosphate significantly inhibited endonuclease VIII-like protein 2 (NEIL2). Pyridoxal phosphate-conjugated NEIL2 completely lost its ability to bind damaged DNA. Reference: Biochem Biophys Res Commun. 2010 Mar 26;394(1):100-5. https://pubmed.ncbi.nlm.nih.gov/20175991/
In vivo activity: Pyridoxal phosphate supplementation was associated with significant benefits in Chlorpromazine (CPZ)-induced Parkinsonism-like changes in mice. Pyridoxal phosphate supplementation was associated with a reduction in CPZ-induced suppression of open-field horizontal locomotion and rearing and a significant increase in grooming activity. A pyridoxal phosphate-supplemented diet was associated with working-memory in CPZ-treated mice and a reduction of anxiety and catalepsy score. Reference: Cent Nerv Syst Agents Med Chem. 2020;20(1):13-25. https://pubmed.ncbi.nlm.nih.gov/31987026/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 10.0 40.46
Water 6.0 24.28

Preparing Stock Solutions

The following data is based on the product molecular weight 247.14 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Ajumeera R, Thipparapu G, Padya BS, Tirumala L, Challa S. Anti-cancer activity of pyridoxal phosphate and metformin combination in human pancreatic cancer cells. Nutr Health. 2022 Nov 8:2601060221137624. doi: 10.1177/02601060221137624. Epub ahead of print. PMID: 36349362. 2. Xie F, Li G, Wang Y, Zhang Y, Zhou L, Wang C, Liu S, Liu S, Wang C. Pyridoxal phosphate synthases PdxS/PdxT are required for Actinobacillus pleuropneumoniae viability, stress tolerance and virulence. PLoS One. 2017 Apr 27;12(4):e0176374. doi: 10.1371/journal.pone.0176374. PMID: 28448619; PMCID: PMC5407770. 3. Olofinnade AT, Onaolapo TM, Oladimeji S, Fatoki AM, Balogun CI, Onaolapo AY, Onaolapo OJ. An Evaluation of the Effects of Pyridoxal Phosphate in Chlorpromazineinduced Parkinsonism using Mice. Cent Nerv Syst Agents Med Chem. 2020;20(1):13-25. doi: 10.2174/1871524920666200120142508. PMID: 31987026. 4. Grin IR, Rieger RA, Zharkov DO. Inactivation of NEIL2 DNA glycosylase by pyridoxal phosphate reveals a loop important for substrate binding. Biochem Biophys Res Commun. 2010 Mar 26;394(1):100-5. doi: 10.1016/j.bbrc.2010.02.121. Epub 2010 Feb 20. PMID: 20175991; PMCID: PMC2857644.
In vitro protocol: 1. Ajumeera R, Thipparapu G, Padya BS, Tirumala L, Challa S. Anti-cancer activity of pyridoxal phosphate and metformin combination in human pancreatic cancer cells. Nutr Health. 2022 Nov 8:2601060221137624. doi: 10.1177/02601060221137624. Epub ahead of print. PMID: 36349362. 2. Xie F, Li G, Wang Y, Zhang Y, Zhou L, Wang C, Liu S, Liu S, Wang C. Pyridoxal phosphate synthases PdxS/PdxT are required for Actinobacillus pleuropneumoniae viability, stress tolerance and virulence. PLoS One. 2017 Apr 27;12(4):e0176374. doi: 10.1371/journal.pone.0176374. PMID: 28448619; PMCID: PMC5407770.
In vivo protocol: 1. Olofinnade AT, Onaolapo TM, Oladimeji S, Fatoki AM, Balogun CI, Onaolapo AY, Onaolapo OJ. An Evaluation of the Effects of Pyridoxal Phosphate in Chlorpromazineinduced Parkinsonism using Mice. Cent Nerv Syst Agents Med Chem. 2020;20(1):13-25. doi: 10.2174/1871524920666200120142508. PMID: 31987026. 2. Grin IR, Rieger RA, Zharkov DO. Inactivation of NEIL2 DNA glycosylase by pyridoxal phosphate reveals a loop important for substrate binding. Biochem Biophys Res Commun. 2010 Mar 26;394(1):100-5. doi: 10.1016/j.bbrc.2010.02.121. Epub 2010 Feb 20. PMID: 20175991; PMCID: PMC2857644.

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1: Dietmann A, Wallner B, König R, Friedrich K, Pfausler B, Deisenhammer F, Griesmacher A, Seger C, Matuja W, JilekAall L, Winkler AS, Schmutzhard E. Nodding syndrome in Tanzania may not be associated with circulating anti-NMDA-and anti-VGKC receptor antibodies or decreased pyridoxal phosphate serum levels-a pilot study. Afr Health Sci. 2014 Jun;14(2):434-8. doi: 10.4314/ahs.v14i2.20. PubMed PMID: 25320594; PubMed Central PMCID: PMC4196418.

2: Xu C, Liao L, He Y, Wu R, Li S, Yang Y. Determination of copper (II) in foodstuffs based on its quenching effect on the fluorescence of N,N'-bis(pyridoxal phosphate)-o-phenylenediamine. Spectrochim Acta A Mol Biomol Spectrosc. 2015;149:662-6. doi: 10.1016/j.saa.2015.04.103. PubMed PMID: 25985131.

3: Smith AM, Brown WC, Harms E, Smith JL. Crystal structures capture three states in the catalytic cycle of a pyridoxal phosphate (PLP) synthase. J Biol Chem. 2015 Feb 27;290(9):5226-39. doi: 10.1074/jbc.M114.626382. PubMed PMID: 25568319; PubMed Central PMCID: PMC4342443.

4: Menon BR, Fisher K, Rigby SE, Scrutton NS, Leys D. A conformational sampling model for radical catalysis in pyridoxal phosphate- and cobalamin-dependent enzymes. J Biol Chem. 2014 Dec 5;289(49):34161-74. doi: 10.1074/jbc.M114.590471. PubMed PMID: 25213862; PubMed Central PMCID: PMC4256349.

5: Goyal M, Fequiere PR, McGrath TM, Hyland K. Seizures with decreased levels of pyridoxal phosphate in cerebrospinal fluid. Pediatr Neurol. 2013 Mar;48(3):227-31. doi: 10.1016/j.pediatrneurol.2012.11.006. PubMed PMID: 23419474.

6: Nodwell MB, Koch MF, Alte F, Schneider S, Sieber SA. A subfamily of bacterial ribokinases utilizes a hemithioacetal for pyridoxal phosphate salvage. J Am Chem Soc. 2014 Apr 2;136(13):4992-9. doi: 10.1021/ja411785r. PubMed PMID: 24601602.

7: Schnell R, Sriram D, Schneider G. Pyridoxal-phosphate dependent mycobacterial cysteine synthases: Structure, mechanism and potential as drug targets. Biochim Biophys Acta. 2015 Sep;1854(9):1175-83. doi: 10.1016/j.bbapap.2014.11.010. Review. PubMed PMID: 25484279.

8: di Salvo ML, Nogués I, Parroni A, Tramonti A, Milano T, Pascarella S, Contestabile R. On the mechanism of Escherichia coli pyridoxal kinase inhibition by pyridoxal and pyridoxal 5'-phosphate. Biochim Biophys Acta. 2015 Sep;1854(9):1160-6. doi: 10.1016/j.bbapap.2015.01.013. PubMed PMID: 25655354.

9: Du YL, Singh R, Alkhalaf LM, Kuatsjah E, He HY, Eltis LD, Ryan KS. A pyridoxal phosphate-dependent enzyme that oxidizes an unactivated carbon-carbon bond. Nat Chem Biol. 2016 Mar;12(3):194-9. doi: 10.1038/nchembio.2009. PubMed PMID: 26807714.

10: Mukherjee T, Hanes J, Tews I, Ealick SE, Begley TP. Pyridoxal phosphate: biosynthesis and catabolism. Biochim Biophys Acta. 2011 Nov;1814(11):1585-96. doi: 10.1016/j.bbapap.2011.06.018. Review. PubMed PMID: 21767669.

11: Carter TC, Pangilinan F, Molloy AM, Fan R, Wang Y, Shane B, Gibney ER, Midttun Ø, Ueland PM, Cropp CD, Kim Y, Wilson AF, Bailey-Wilson JE, Brody LC, Mills JL. Common Variants at Putative Regulatory Sites of the Tissue Nonspecific Alkaline Phosphatase Gene Influence Circulating Pyridoxal 5'-Phosphate Concentration in Healthy Adults. J Nutr. 2015 Jul;145(7):1386-93. doi: 10.3945/jn.114.208769. PubMed PMID: 25972531; PubMed Central PMCID: PMC4478949.

12: Jochmann N, Götker S, Tauch A. Positive transcriptional control of the pyridoxal phosphate biosynthesis genes pdxST by the MocR-type regulator PdxR of Corynebacterium glutamicum ATCC 13032. Microbiology. 2011 Jan;157(Pt 1):77-88. doi: 10.1099/mic.0.044818-0. PubMed PMID: 20847010.

13: Kobayashi D, Yoshimura T, Johno A, Ishikawa M, Sasaki K, Wada K. Decrease in pyridoxal-5'-phosphate concentration and increase in pyridoxal concentration in rat plasma by 4'-O-methylpyridoxine administration. Nutr Res. 2015 Jul;35(7):637-42. doi: 10.1016/j.nutres.2015.05.015. PubMed PMID: 26092494.

14: Lai RY, Huang S, Fenwick MK, Hazra A, Zhang Y, Rajashankar K, Philmus B, Kinsland C, Sanders JM, Ealick SE, Begley TP. Thiamin pyrimidine biosynthesis in Candida albicans : a remarkable reaction between histidine and pyridoxal phosphate. J Am Chem Soc. 2012 Jun 6;134(22):9157-9. doi: 10.1021/ja302474a. PubMed PMID: 22568620; PubMed Central PMCID: PMC3415583.

15: Huang S, Yao L, Zhang J, Huang L. Direct and indirect effects of RNA interference against pyridoxal kinase and pyridoxine 5'-phosphate oxidase genes in Bombyx mori. Gene. 2016 Aug 1;587(1):48-52. doi: 10.1016/j.gene.2016.04.035. PubMed PMID: 27106120.

16: Nooij LS, van Eyck J, Klip H, van de Leur JJ, Bosma JP. The reliability of methionine challenge test is not affected by a deficiency in pyridoxal phosphate, folic acid, or cobalamin. Hypertens Pregnancy. 2011;30(1):11-7. doi: 10.3109/10641955.2010.484078. PubMed PMID: 20818966.

17: Knobloch G, Jabari N, Stadlbauer S, Schindelin H, Köhn M, Gohla A. Synthesis of hydrolysis-resistant pyridoxal 5'-phosphate analogs and their biochemical and X-ray crystallographic characterization with the pyridoxal phosphatase chronophin. Bioorg Med Chem. 2015 Jun 15;23(12):2819-27. doi: 10.1016/j.bmc.2015.02.049. PubMed PMID: 25783190.

18: Miles EW. The tryptophan synthase α2β2 complex: a model for substrate channeling, allosteric communication, and pyridoxal phosphate catalysis. J Biol Chem. 2013 Apr 5;288(14):10084-91. doi: 10.1074/jbc.X113.463331. PubMed PMID: 23426371; PubMed Central PMCID: PMC3617248.

19: Adelufosi AO, Abayomi O, Ojo TM. Pyridoxal 5 phosphate for neuroleptic-induced tardive dyskinesia. Cochrane Database Syst Rev. 2015 Apr 13;(4):CD010501. doi: 10.1002/14651858.CD010501.pub2. Review. PubMed PMID: 25866243.

20: Vasilaki AT, McMillan DC, Kinsella J, Duncan A, O'Reilly DS, Talwar D. Relation between pyridoxal and pyridoxal phosphate concentrations in plasma, red cells, and white cells in patients with critical illness. Am J Clin Nutr. 2008 Jul;88(1):140-6. PubMed PMID: 18614734.