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MedKoo Cat#: 561637 | Name: Polyoxin B
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Description:

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

Polyoxin B belongs to a group of nucleoside antibiotics composed of heterocyclic moieties containing nitrogen. Polyoxins (including Polyoxin B) work by inhibiting the biosynthesis of chitin.

Chemical Structure

Polyoxin B
Polyoxin B
CAS#19396-06-6

Theoretical Analysis

MedKoo Cat#: 561637

Name: Polyoxin B

CAS#: 19396-06-6

Chemical Formula: C17H25N5O13

Exact Mass: 507.1449

Molecular Weight: 507.40

Elemental Analysis: C, 40.24; H, 4.97; N, 13.80; O, 40.99

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 750.00 2 Weeks
50mg USD 1,250.00 2 Weeks
100mg USD 1,950.00 2 Weeks
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Related CAS #
No Data
Synonym
Polyoxin B; Polyoxin-B;
IUPAC/Chemical Name
(2S)-2-[[(2S,3S,4S)-2-Amino-5-carbamoyloxy-3,4-dihydroxypentanoyl]amino]-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[5-(hydroxymethyl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]acetic acid
InChi Key
YFZNSPMAOIVQRP-YVKGXWRCSA-N
InChi Code
InChI=1S/C17H25N5O13/c18-6(8(25)5(24)3-34-16(19)32)13(29)20-7(15(30)31)11-9(26)10(27)14(35-11)22-1-4(2-23)12(28)21-17(22)33/h1,5-11,14,23-27H,2-3,18H2,(H2,19,32)(H,20,29)(H,30,31)(H,21,28,33)/t5-,6-,7-,8+,9-,10+,11+,14+/m0/s1
SMILES Code
O=C(O)[C@@H](NC([C@@H](N)[C@H](O)[C@@H](O)COC(N)=O)=O)[C@H]1O[C@@H](N(C(N2)=O)C=C(CO)C2=O)[C@H](O)[C@@H]1O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 507.40 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
1: Liu L, Wu H, Long Y, Yang X, Du C, Xu Y, Ji Q. Novel spiro[pyrrolidine-2,3'-quinoline]-2'-one derivatives containing piperazine fragment as potential chitin synthase inhibitors and antifungal agents: Design, synthesis and biological evaluation. Eur J Med Chem. 2023 Nov 15;260:115777. doi: 10.1016/j.ejmech.2023.115777. Epub 2023 Aug 30. PMID: 37660485. 2: Du C, Yang X, Long Y, Lang X, Liu L, Xu Y, Wu H, Chu Y, Hu X, Deng J, Ji Q. Design, synthesis and biological evaluation of novel spiro-quinazolinone derivatives as chitin synthase inhibitors and antifungal agents. Eur J Med Chem. 2023 Jul 5;255:115388. doi: 10.1016/j.ejmech.2023.115388. Epub 2023 Apr 26. PMID: 37141707. 3: Xu Y, Shen Y, Du C, Liu L, Wu H, Ji Q. Spiro[benzoxazine-piperidin]-one derivatives as chitin synthase inhibitors and antifungal agents: Design, synthesis and biological evaluation. Eur J Med Chem. 2022 Dec 5;243:114723. doi: 10.1016/j.ejmech.2022.114723. Epub 2022 Aug 31. PMID: 36070631. 4: Yoshinari T, Watanabe M, Hara-Kudo Y. Cross-genus inhibitory activity of polyoxins against aflatoxin production by Aspergillus parasiticus and fumonisin production by Fusarium fujikuroi. FEMS Microbiol Lett. 2022 Jul 28;369(1):fnac048. doi: 10.1093/femsle/fnac048. PMID: 35641197. 5: Wu H, Du C, Xu Y, Liu L, Zhou X, Ji Q. Design, synthesis, and biological evaluation of novel spiro[pyrrolidine-2,3'-quinolin]-2'-one derivatives as potential chitin synthase inhibitors and antifungal agents. Eur J Med Chem. 2022 Apr 5;233:114208. doi: 10.1016/j.ejmech.2022.114208. Epub 2022 Feb 22. PMID: 35220015. 6: Zhou M, Hu C, Yin Y, Wang J, Ye S, Yu Y, Sun X, Li S. Experimental Evolution of Multidrug Resistance in Neurospora crassa under Antifungal Azole Stress. J Fungi (Basel). 2022 Feb 18;8(2):198. doi: 10.3390/jof8020198. PMID: 35205952; PMCID: PMC8875772. 7: Ji Q, Li B, Chu Y, Wu H, Du C, Xu Y, Shen Y, Deng J. Design, synthesis and biological evaluation of novel diazaspirodecanone derivatives containing piperidine-4-carboxamide as chitin synthase inhibitors and antifungal agents. Bioorg Chem. 2021 Sep;114:105108. doi: 10.1016/j.bioorg.2021.105108. Epub 2021 Jun 22. PMID: 34175721. 8: Li Z, Jiang D, Dai Y, Dai Z, Jin Y, Fu Q, Liang X. Isolation of three polyoxins by reversed-phase liquid chromatography with pure aqueous mobile phase. J Sep Sci. 2021 May;44(10):2020-2028. doi: 10.1002/jssc.202001181. Epub 2021 May 2. PMID: 33629802. 9: Nagatomo M, Inoue M. Convergent Assembly of Highly Oxygenated Natural Products Enabled by Intermolecular Radical Reactions. Acc Chem Res. 2021 Feb 2;54(3):595-604. doi: 10.1021/acs.accounts.0c00792. Epub 2021 Jan 6. PMID: 33406830. 10: Li W, Dai X, Pu E, Bian H, Chen Z, Zhang X, Guo Z, Li P, Li H, Yong Y, Wang C, Zhang Y, Han L. HLB-MCX-Based Solid-Phase Extraction Combined with Liquid Chromatography-Tandem Mass Spectrometry for the Simultaneous Determination of Four Agricultural Antibiotics (Kasugamycin, Validamycin A, Ningnanmycin, and Polyoxin B) Residues in Plant-Origin Foods. J Agric Food Chem. 2020 Nov 25;68(47):14025-14037. doi: 10.1021/acs.jafc.0c04620. Epub 2020 Nov 15. PMID: 33190501. 11: Ranganathan S, Ampasala DR, Palaka BK, Ilavarasi AV, Patidar I, Poovadan LP, Sapam TD. In silico Binding Profile Analysis and In vitro Investigation on Chitin Synthase Substrate and Inhibitors from Maize Stem Borer, Chilo partellus. Curr Comput Aided Drug Des. 2021;17(7):881-895. doi: 10.2174/1573409916666201013150920. PMID: 33109065. 12: Li B, Shen Y, Wu H, Wu X, Yuan L, Ji Q. Design, synthesis and biological evaluation of novel 3,4-dihydro-2(1H)-quinolinone derivatives as potential chitin synthase inhibitors and antifungal agents. Eur J Med Chem. 2020 Jun 1;195:112278. doi: 10.1016/j.ejmech.2020.112278. Epub 2020 Apr 4. PMID: 32283299. 13: Li B, Wang K, Zhang R, Li B, Shen Y, Ji Q. Design, synthesis and biological evaluation of novel diazaspiro[4.5]decan-1-one derivatives as potential chitin synthase inhibitors and antifungal agents. Eur J Med Chem. 2019 Nov 15;182:111669. doi: 10.1016/j.ejmech.2019.111669. Epub 2019 Aug 31. PMID: 31494473. 14: Ji Q, Deng Q, Li B, Li B, Shen Y. Design, synthesis and biological evaluation of novel 5-(piperazin-1-yl)quinolin-2(1H)-one derivatives as potential chitin synthase inhibitors and antifungal agents. Eur J Med Chem. 2019 Oct 15;180:204-212. doi: 10.1016/j.ejmech.2019.07.035. Epub 2019 Jul 10. PMID: 31306907. 15: Noureldin NA, Kothayer H, Lashine EM, Baraka MM, Huang Y, Li B, Ji Q. Design, synthesis and biological evaluation of novel quinazoline-2,4-diones conjugated with different amino acids as potential chitin synthase inhibitors. Eur J Med Chem. 2018 May 25;152:560-569. doi: 10.1016/j.ejmech.2018.05.001. Epub 2018 May 4. PMID: 29763805. 16: Konno K, Shimura S, Ueno C, Arakawa T, Nakamura M. Abnormal swelling of the peritrophic membrane in Eri silkworm gut caused by MLX56 family defense proteins with chitin-binding and extensin domains. Phytochemistry. 2018 Mar;147:211-219. doi: 10.1016/j.phytochem.2018.01.005. PMID: 29406091. 17: Dowling ME, Hu MJ, Schnabel G. Identification and Characterization of Botrytis fragariae Isolates on Strawberry in the United States. Plant Dis. 2017 Oct;101(10):1769-1773. doi: 10.1094/PDIS-03-17-0316-RE. Epub 2017 Aug 1. PMID: 30676928. 18: Fujino H, Nagatomo M, Paudel A, Panthee S, Hamamoto H, Sekimizu K, Inoue M. Unified Total Synthesis of Polyoxins J, L, and Fluorinated Analogues on the Basis of Decarbonylative Radical Coupling Reactions. Angew Chem Int Ed Engl. 2017 Sep 18;56(39):11865-11869. doi: 10.1002/anie.201706671. Epub 2017 Aug 17. PMID: 28727238. 19: Dowling ME, Hu MJ, Schmitz LT, Wilson JR, Schnabel G. Characterization of Botrytis cinerea Isolates from Strawberry with Reduced Sensitivity to Polyoxin D Zinc Salt. Plant Dis. 2016 Oct;100(10):2057-2061. doi: 10.1094/PDIS-02-16-0166-RE. Epub 2016 Jul 13. PMID: 30683012. 20: Volkova VN, Mukhina LP, Chistova ZA, Fedorova SG. [Determination of polioksin B in the air environment and in washouts from skin of operators by HPLC]. Gig Sanit. 2016;95(11):1105-7. Russian. PMID: 29446275.

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Bietamiverine