Synonym
BN 227; BN227; BN-227; Antibiotic BN 227; G 1549; Cepabactin
IUPAC/Chemical Name
2(1H)-Pyridinone, 1-hydroxy-5-methoxy-6-methyl-
InChi Key
SVCUBTJFRYLVSI-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H9NO3/c1-5-6(11-2)3-4-7(9)8(5)10/h3-4,10H,1-2H3
SMILES Code
O=C1C=CC(OC)=C(C)N1O
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
155.15
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: Itoh J, Miyadoh S, Takahasi S, Amano S, Ezaki N, Yamada Y. Studies on antibiotics BN-227 and BN-227-F, new antibiotics. I. Taxonomy, isolation and characterization. J Antibiot (Tokyo). 1979 Nov;32(11):1089-95. doi: 10.7164/antibiotics.32.1089. PMID: 528378.
2: Itoh J, Amano S, Ogawa Y, Kodama Y, Ezaki N, Yamada Y. Studies on antibiotics BN-227 and BN-227-F, new antibiotics. II. Chemical structure of antibiotics BN-227 and BN-227-F. J Antibiot (Tokyo). 1980 Apr;33(4):377-82. doi: 10.7164/antibiotics.33.377. PMID: 7410206.
3: Li D, Oku N, Hasada A, Shimizu M, Igarashi Y. Two new 2-alkylquinolones, inhibitory to the fish skin ulcer pathogen Tenacibaculum maritimum, produced by a rhizobacterium of the genus Burkholderia sp. Beilstein J Org Chem. 2018 Jun 14;14:1446-1451. doi: 10.3762/bjoc.14.122. PMID: 29977408; PMCID: PMC6009182.
4: Thomas MS. Iron acquisition mechanisms of the Burkholderia cepacia complex. Biometals. 2007 Jun;20(3-4):431-52. doi: 10.1007/s10534-006-9065-4. Epub 2007 Feb 13. Erratum in: Biometals. 2008 Feb;21(1):105-6. PMID: 17295049.
5: Klumpp C, Burger A, Mislin GL, Abdallah MA. From a total synthesis of cepabactin and its 3:1 ferric complex to the isolation of a 1:1:1 mixed complex between iron (III), cepabactin and pyochelin. Bioorg Med Chem Lett. 2005 Mar 15;15(6):1721-4. doi: 10.1016/j.bmcl.2005.01.034. PMID: 15745828.
6: Darling P, Chan M, Cox AD, Sokol PA. Siderophore production by cystic fibrosis isolates of Burkholderia cepacia. Infect Immun. 1998 Feb;66(2):874-7. doi: 10.1128/IAI.66.2.874-877.1998. PMID: 9453660; PMCID: PMC107988.
7: Castignetti D. Probing of Pseudomonas aeruginosa, Pseudomonas aureofaciens, Burkholderia (Pseudomonas) cepacia, Pseudomonas fluorescens, and Pseudomonas putida with the ferripyochelin receptor A gene and the synthesis of pyochelin in Pseudomonas aureofaciens, Pseudomonas fluorescens, and Pseudomonas putida. Curr Microbiol. 1997 Apr;34(4):250-7. doi: 10.1007/s002849900178. PMID: 9058547.
