Synonym
NSC 204855, Steffimycin B, U 40615
IUPAC/Chemical Name
(2S,3S,4R)-4-[(6-deoxy-2,4-di-O-methyl-α-L-mannopyranosyl)oxy]-3,4-dihydro-2,5,7-trihydroxy-3,9-dimethoxy-2-methyl-1,6,11(2H)-naphthacenetrione
InChi Key
VHJWDTPKSIFZBV-IDORXPLKSA-N
InChi Code
InChI=1S/C29H32O13/c1-10-23(38-4)22(34)25(39-5)28(41-10)42-24-18-14(26(35)29(2,36)27(24)40-6)9-13-17(21(18)33)20(32)16-12(19(13)31)7-11(37-3)8-15(16)30/h7-10,22-25,27-28,30,33-34,36H,1-6H3/t10-,22+,23-,24+,25+,27-,28-,29+/m0/s1
SMILES Code
OC1=CC(OC)=CC2=C1C(C(C(O)=C([C@@H](O[C@]3([H])O[C@@H](C)[C@H](OC)[C@@H](O)[C@H]3OC)[C@H](OC)[C@](C)(O)C4=O)C4=C5)=C5C2=O)=O
Appearance
A lyophilisate
Purity
>99% (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
Biological target:
Steffimycin B is cytotoxic to MCF-7, KB, NCI-H187, and Vero cells (IC50s = 3.5, 6.75, 3.28, and 10.5 μM, respectively). It is active against M. tuberculosis (MIC = 5.2 nM), B. cereus (MIC = 1.56 μg/ml), and P. falciparum (IC50 = 2.19 μM). It binds to DNA, preferentially intercalating at sites containing cytosine and guanine.
In vitro activity:
Endophyte-derived compounds such as steffimycin B have potential for tuberculosis treatment. Steffimycin B displayed a good activity against M. tuberculosis H37Rv ATCC 27294 strain, with MIC100 and SI values of 7.8 µg/mL and 6.42, respectively. When tested against the rifampin mono resistant M. tuberculosis Mtb-209 pathogen strain, a better activity was observed (MIC100 of 3.9 µg/mL), suggesting a different action mechanism of StefB from that of rifampin.
Reference: Mol Biol Rep. 2018 Dec;45(6):2563-2570. https://pubmed.ncbi.nlm.nih.gov/30311126/
In vivo activity:
To be determined
Preparing Stock Solutions
The following data is based on the
product
molecular weight
588.56
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. Trenado-Uribe M, Silva-Miranda M, Rivero-Cruz JF, Rodríguez-Peña K, Espitia-Pinzón CI, Rodríguez-Sanoja R, Sánchez S. Antimycobacterial activity of an anthracycline produced by an endophyte isolated from Amphipterygium adstringens. Mol Biol Rep. 2018 Dec;45(6):2563-2570. doi: 10.1007/s11033-018-4424-0. Epub 2018 Oct 11. PMID: 30311126.
In vitro protocol:
1. Trenado-Uribe M, Silva-Miranda M, Rivero-Cruz JF, Rodríguez-Peña K, Espitia-Pinzón CI, Rodríguez-Sanoja R, Sánchez S. Antimycobacterial activity of an anthracycline produced by an endophyte isolated from Amphipterygium adstringens. Mol Biol Rep. 2018 Dec;45(6):2563-2570. doi: 10.1007/s11033-018-4424-0. Epub 2018 Oct 11. PMID: 30311126.
In vivo protocol:
To be determined
1. Trenado-Uribe, M., Silva-Miranda, M., Rivero-Cruz, J.F., et al. Antimycobacterial activity of an anthracycline produced by an endophyte isolated from Amphipterygium adstringens. Mol. Biol. Rep. 45(6), 2563-2570 (2018).
2. Jones, M.B., Holistein, U., and Allen, F.S. Site specificity of binding of antitumor antibiotics to DNA. Biopolymers 26(1), 121-135 (1987).
3. Intaraudom, C., Bunbamrung, N., Dramae, A., et al. Antimalarial and antimycobacterial agents from Streptomyces sp. BCC27095. Tetrahedron Lett. 56(49), 6875-6877 (2015).
