Pyridoxatin | CAS# 135529-30-5 | Fungal Metabolite

MedKoo Cat#: 574158 | Name: Pyridoxatin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pyridoxatin is a fungal metabolite that inhibits production of thiobarbituric acid reactive substance (TBARS). Pyridoxatin inhibits hemolysis induced by the free radical generator AAPH and is active against C. albicans.

Chemical Structure

Pyridoxatin

CAS#135529-30-5

Theoretical Analysis

MedKoo Cat#: 574158

Name: Pyridoxatin

CAS#: 135529-30-5

Chemical Formula: C15H21NO3

Exact Mass: 263.1521

Molecular Weight: 263.34

Elemental Analysis: C, 68.42; H, 8.04; N, 5.32; O, 18.23

Price and Availability

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1mg	USD 300.00

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Synonym

Pyridoxatin

IUPAC/Chemical Name

3-[(1R,2S,4R,6S)-2-ethenyl-4,6-dimethylcyclohexyl]-1,4-dihydroxy-2(1H)-pyridinone

InChi Key

OQJADHLOEAOIGC-LSCVPOLPSA-N

InChi Code

InChI=1S/C15H21NO3/c1-4-11-8-9(2)7-10(3)13(11)14-12(17)5-6-16(19)15(14)18/h4-6,9-11,13,17,19H,1,7-8H2,2-3H3/t9-,10+,11-,13-/m1/s1

SMILES Code

C[C@H]1C[C@@H](C=C)[C@H](C2=C(O)C=CN(O)C2=O)[C@@H](C)C1

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

To be determined

Shelf Life

>3 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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Pyridoxatin inhibits the production of TBARS in vitro (IC50 = 0.55 μg/ml). Pyridoxatin inhibits hemolysis induced by the free radical generator AAPH in rat erythrocytes (IC50 = 1.95 μg/ml). It is active against C. albicans (MIC = 1.64 μg/ml). Pyridoxatin is cytotoxic in a panel of 21 cancer cell lines (EC50s = 0.10-7.04 μg/ml). It also inhibits gelatinase A (IC50 = 15.2 μM).

In vitro activity:

Pyridoxatin is a promising alternative to desferrioxamine for iron chelation therapy due to its cell permeability. This study explored fungal hydroxamates as potential stress mitigators under iron overload conditions. All fungal chelators (in aqueous medium) and py pyridoxatin ridoxatin and desferriastechrome (in cells), were strong iron scavengers. Only pyridoxatin and desferricoprogen (in buffered medium) or pyridoxatin (in cells) had antioxidant effects against two types of iron-dependent oxidative stress. Reference: Biometals. 2019 Aug;32(4):707-715. https://pubmed.ncbi.nlm.nih.gov/31152280/

In vivo activity:

To be determined

Preparing Stock Solutions

The following data is based on the product molecular weight 263.34 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.

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. da Silva GS, Shang Z, Kalansuriya P, Capon RJ, Espósito BP. Antioxidant activity and cellular uptake of the hydroxamate-based fungal iron chelators pyridoxatin, desferriastechrome and desferricoprogen. Biometals. 2019 Aug;32(4):707-715. doi: 10.1007/s10534-019-00202-7. Epub 2019 Jun 1. PMID: 31152280. 2. Chang W, Zhang M, Li Y, Li X, Gao Y, Xie Z, Lou H. Lichen endophyte derived pyridoxatin inactivates Candida growth by interfering with ergosterol biosynthesis. Biochim Biophys Acta. 2015 Sep;1850(9):1762-71. doi: 10.1016/j.bbagen.2015.05.005. Epub 2015 May 8. PMID: 25960388.

In vitro protocol:

In vivo protocol:

To be determined

1. Teshima, Y., Shin-ya, K., Shuimazu, A., et al. Isolation and structural elucidation of pyridoxatin, a free radical scavenger of microbial origin. J. Antibiot. (Tokyo) 44(6), 685-687 (1991). 2. Lee, H.-J., Chung, M.-C., Lee, C.-H., et al. Pyridoxatin, an inhibitor of gelatinase A with cytotoxic activity. J. Microbiol. Biotechnol. 6(6), 445-450 (1996).