Synonym
MM 47755; MM-47755
IUPAC/Chemical Name
Benz(a)anthracene-1,7,12(2H)-trione, 3,4-dihydro-3-hydroxy-8-methoxy-3-methyl-, (-)-
InChi Key
XZLGWJORNHETKI-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H16O5/c1-20(24)8-10-6-7-12-17(15(10)13(21)9-20)19(23)11-4-3-5-14(25-2)16(11)18(12)22/h3-7,24H,8-9H2,1-2H3
SMILES Code
O=C1CC(C)(O)CC(C1=C2C3=O)=CC=C2C(C4=C3C=CC=C4OC)=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
Biological target:
MM 47755 is a new benz[a]anthracene antibiotic from a streptomycete.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
336.34
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 |
1: Kesenheimer C, Groth U. Total synthesis of (-)-8-O-methyltetrangomycin (MM 47755). Org Lett. 2006 Jun 8;8(12):2507-10. PubMed PMID: 16737300.
2: Hadj Rabia-Boukhalfa Y, Eveno Y, Karama S, Selama O, Lauga B, Duran R, Hacène H, Eparvier V. Isolation, purification and chemical characterization of a new angucyclinone compound produced by a new halotolerant Nocardiopsis sp. HR-4 strain. World J Microbiol Biotechnol. 2017 Jun;33(6):126. doi: 10.1007/s11274-017-2292-8. Epub 2017 May 25. PubMed PMID: 28547727.
3: Kaliappan KP, Ravikumar V. Angucyclinone antibiotics: total syntheses of YM-181741, (+)-ochromycinone, (+)-rubiginone B2, (-)-tetrangomycin, and MM-47755. J Org Chem. 2007 Aug 3;72(16):6116-26. Epub 2007 Jul 11. PubMed PMID: 17625884.
4: Gilpin ML, Balchin J, Box SJ, Tyler JW. MM 47755, a new benz[a]anthracene antibiotic from a streptomycete. J Antibiot (Tokyo). 1989 Apr;42(4):627-8. PubMed PMID: 2722675.
5: Nemoto K, Hayashi M, Sugawara Y, Ito J, Abe F, Takita T, Nakamura T, Takeuchi T. Biological activities of deoxyspergualin in autoimmune disease mice. J Antibiot (Tokyo). 1988 Sep;41(9):1253-9. PubMed PMID: 3263348.
6: Sakai K, Koyama N, Fukuda T, Mori Y, Onaka H, Tomoda H. Search method for inhibitors of Staphyloxanthin production by methicillin-resistant Staphylococcus aureus. Biol Pharm Bull. 2012;35(1):48-53. PubMed PMID: 22223336.
7: Kesenheimer C, Kalogerakis A, Meissner A, Groth U. The cobalt way to angucyclinones: asymmetric total synthesis of the antibiotics (+)-rubiginone B2, (-)-tetrangomycin, and (-)-8-O-methyltetrangomycin. Chemistry. 2010 Aug 2;16(29):8805-21. doi: 10.1002/chem.201000804. PubMed PMID: 20575121.
8: Jiménez JT, Sturdíková M, Brezová V, Svajdlenka E, Novotová M. Screening of mutant strain Streptomyces mediolani sp. AC37 for (-)-8-O-methyltetrangomycin production enhancement. J Microbiol. 2012 Dec;50(6):1014-23. doi: 10.1007/s12275-012-2025-5. Epub 2012 Dec 30. PubMed PMID: 23274989.
