Synonym
Simaomicin alpha; LL D42067alpha; LL-D42067alpha; L D42067alpha;
IUPAC/Chemical Name
(7aR,11S,14R)-11,14,16,17-tetrahydroxy-9-methoxy-2,3-dimethyl-7a,8,11,12,13,14-hexahydro-2H-chromeno[3',2':6,7][1,3]dioxino[4',5',6':10,1]phenanthro[3,2-c]pyridine-1,15-dione
InChi Key
DQPBSXMRMTWOAQ-HZSPNIEDSA-N
InChi Code
InChI=1S/C28H25NO10/c1-9-6-10-16(28(35)29(9)2)22(33)19-15-11(7-14-18(19)24(10)38-8-37-14)25(36-3)27-20(21(15)32)23(34)17-12(30)4-5-13(31)26(17)39-27/h6,12-14,30-33H,4-5,7-8H2,1-3H3/t12-,13+,14-/m1/s1
SMILES Code
O[C@H]1CC[C@@H](O)c2c(c3c(O)c(c(c4c(OCO[C@@H]4C5)c6cc(C)n7C)c(O)c6c7=O)c5c(OC)c3oc21)=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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
535.50
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: Ishiyama A, Otoguro K, Namatame M, Nishihara A, Furusawa T, Takahashi Y, Masuma R, Shiomi K, Omura S. Simaomicin alpha: effects on the cell cycle of synchronized, cultured Plasmodium falciparum. J Antibiot (Tokyo). 2008 Apr;61(4):254-7. doi: 10.1038/ja.2008.38. PubMed PMID: 18503207.
2: Arai M, Sato H, Kobayashi H, Suganuma M, Kawabe T, Tomoda H, Omura S. Selective inhibition of bleomycin-induced G2 cell cycle checkpoint by simaomicin alpha. Biochem Biophys Res Commun. 2004 May 7;317(3):817-22. PubMed PMID: 15081413.
3: Maiese WM, Korshalla J, Goodman J, Torrey MJ, Kantor S, Labeda DP, Greenstein M. Simaomicin (LL-D42067), a novel antibiotic from Actinomadura madurae. I. Taxonomy, fermentation and biological activity. J Antibiot (Tokyo). 1990 Sep;43(9):1059-63. PubMed PMID: 2211367.
4: Koizumi Y, Tomoda H, Kumagai A, Zhou XP, Koyota S, Sugiyama T. Simaomicin α, a polycyclic xanthone, induces G₁ arrest with suppression of retinoblastoma protein phosphorylation. Cancer Sci. 2009 Feb;100(2):322-6. doi: 10.1111/j.1349-7006.2008.01033.x. PubMed PMID: 19077005.
5: Wang Y, Wang C, Butler JR, Ready JM. Dehydrogenative coupling to enable the enantioselective total synthesis of (-)-simaomicin α. Angew Chem Int Ed Engl. 2013 Oct 4;52(41):10796-9. doi: 10.1002/anie.201304812. Epub 2013 Aug 22. PubMed PMID: 24038677; PubMed Central PMCID: PMC3966973.
6: Ui H, Ishiyama A, Sekiguchi H, Namatame M, Nishihara A, Takahashi Y, Shiomi K, Otoguro K, Omura S. Selective and potent in vitro antimalarial activities found in four microbial metabolites. J Antibiot (Tokyo). 2007 Mar;60(3):220-2. PubMed PMID: 17446697.
