Synonym
Myxin; 3C Antibiotic
IUPAC/Chemical Name
1-Phenazinol, 6-methoxy-, 5,10-dioxide
InChi Key
JIDVGUQUQSOHOL-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H10N2O4/c1-19-11-7-3-5-9-13(11)15(18)8-4-2-6-10(16)12(8)14(9)17/h2-7,16H,1H3
SMILES Code
OC1=CC=CC2=C1[N+]([O-])=C3C=CC=C(OC)C3=[N+]2[O-]
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
>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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
258.23
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 |
1: Chowdhury G, Sarkar U, Pullen S, Wilson WR, Rajapakse A, Fuchs-Knotts T, Gates KS. DNA strand cleavage by the phenazine di-N-oxide natural product myxin under both aerobic and anaerobic conditions. Chem Res Toxicol. 2012 Jan 13;25(1):197-206. doi: 10.1021/tx2004213. Epub 2011 Nov 22. PubMed PMID: 22084973.
2: Lesley SM, Behki RM. Mode of action of myxin on Escherichia coli. J Bacteriol. 1967 Dec;94(6):1837-45. PubMed PMID: 4864404; PubMed Central PMCID: PMC276912.
3: Viktorsson EÖ, Melling Grøthe B, Aesoy R, Sabir M, Snellingen S, Prandina A, Høgmoen Åstrand OA, Bonge-Hansen T, Døskeland SO, Herfindal L, Rongved P. Total synthesis and antileukemic evaluations of the phenazine 5,10-dioxide natural products iodinin, myxin and their derivatives. Bioorg Med Chem. 2017 Apr 1;25(7):2285-2293. doi: 10.1016/j.bmc.2017.02.058. Epub 2017 Feb 28. PubMed PMID: 28284865.
4: Behki RM, Lesley SM. Effect of myxin on deoxyribonucleic acid synthesis in Escherichia coli infected with T4 bacteriophage. J Virol. 1971 Mar;7(3):372-8. PubMed PMID: 4927527; PubMed Central PMCID: PMC356127.
5: Sekhon AS, Hargesheimer E. Sensitivity of some human pathogenic yeasts and systemic fungi to myxin. J Clin Pathol. 1975 Jul;28(7):547-9. PubMed PMID: 1171116; PubMed Central PMCID: PMC475769.
6: Weigele M, Leimgruber W. The structure of myxin. Tetrahedron Lett. 1967 Feb;8:715-8. PubMed PMID: 6044208.
7: Behki RM, Lesley SM. Deoxyribonucleic acid degradation and the lethal effect by myxin in Escherichia coli. J Bacteriol. 1972 Jan;109(1):250-61. PubMed PMID: 4550666; PubMed Central PMCID: PMC247274.
8: Jiang J, Guiza Beltran D, Schacht A, Wright S, Zhang L, Du L. Functional and Structural Analysis of Phenazine O-Methyltransferase LaPhzM from Lysobacter antibioticus OH13 and One-Pot Enzymatic Synthesis of the Antibiotic Myxin. ACS Chem Biol. 2018 Apr 20;13(4):1003-1012. doi: 10.1021/acschembio.8b00062. Epub 2018 Mar 12. PubMed PMID: 29510028; PubMed Central PMCID: PMC5910208.
9: Lesley SM, Behki RM. Induction of phage formation in lysogenic Escherichia coli by myxin. J Gen Microbiol. 1972 Jun;71(1):195-7. PubMed PMID: 4556973.
10: Weigele M, Maestrone G, Mitrovic M, Leimgruber W. Antimicrobial agents structurally related to myxin. Antimicrob Agents Chemother (Bethesda). 1970;10:46-9. PubMed PMID: 5521369.
11: Hanson AW. The crystal structure of myxin. Acta Crystallogr B. 1968 Aug 15;24(8):1084-96. PubMed PMID: 5756988.
12: Peterson EA. Activity of myxin against ceratocystis ulmi. Can J Microbiol. 1969 Jan;15(1):133-5. PubMed PMID: 5765172.
13: Hartman PE, Berger H, Hartman Z. Comparison of hycanthone ("etrenol"), some hycanthone analogs, myxin and 4-nitroquinoline-1-oxide as frameshift mutagens. J Pharmacol Exp Ther. 1973 Sep;186(3):390-8. PubMed PMID: 4580578.
14: Lesley SM, Behki RM. Recovery of metabolic activity in Escherichia coli following limited exposure to myxin. Can J Microbiol. 1971 Oct;17(10):1327-33. PubMed PMID: 4943486.
15: Lesley SM, Behki RM, Gillespie DC. Production of radioactive myxin. Can J Microbiol. 1967 Sep;13(9):1251-7. PubMed PMID: 6054681.
16: Manius G, Tscherne R, Venteicher R, Secker A. High-performance liquid chromatographic determination of free myxin and its reduction product as impurities in cuprimyxin-containing creams. J Pharm Sci. 1981 Sep;70(9):1024-6. PubMed PMID: 6101146.
17: McCalla DR, Baerg W. Action of myxin on the chloroplast system of Euglena gracilis. J Protozool. 1969 Aug;16(3):425-8. PubMed PMID: 5343458.
18: Stevenson IL. The effect of myxin on membrane synthesis in Escherichia coli. Can J Microbiol. 1970 Dec;16(12):1249-53. PubMed PMID: 4107097.
19: Sekhon AS. Sensitivity of Scopulariopsis brevicaulis to some antimicrobial agents. Mycopathologia. 1975 Dec 31;57(3):177-9. PubMed PMID: 1240599.
20: Lesley SM, Behki RM. Sensitivity to myxin of Escherichia coli treated with ethylenediaminetetraacetic acid. Can J Microbiol. 1973 Apr;19(4):531-3. PubMed PMID: 4633656.
