Synonym
Shermilamine B; Debromoshermilamine A.
IUPAC/Chemical Name
Acetamide, N-(2-(8,11,12,13-tetrahydro-12-oxopyrido(4,3,2-mn)(1,4)thiazino(3,2-b)acridin-9-yl)ethyl)-
InChi Key
IHFPKDUIXNIBMM-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H18N4O2S/c1-11(26)22-8-7-14-18-17-13(12-4-2-3-5-15(12)24-18)6-9-23-19(17)20-21(14)28-10-16(27)25-20/h2-6,9,24H,7-8,10H2,1H3,(H,22,26)(H,25,27)
SMILES Code
CC(NCCC(C(SCC(N1)=O)=C1C2=NC=CC3=C42)=C4NC5=C3C=CC=C5)=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
390.46
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: Bontemps N, Gattacceca F, Long C, Thomas OP, Banaigs B. Additional cytotoxic pyridoacridine alkaloids from the ascidian Cystodytes violatinctus and biogenetic considerations. J Nat Prod. 2013 Sep 27;76(9):1801-5. doi: 10.1021/np400284z. Epub 2013 Aug 20. PubMed PMID: 23961991.
2: Bontemps N, Bry D, López-Legentil S, Simon-Levert A, Long C, Banaigs B. Structures and antimicrobial activities of pyridoacridine alkaloids isolated from different chromotypes of the ascidian Cystodytes dellechiajei. J Nat Prod. 2010 Jun 25;73(6):1044-8. doi: 10.1021/np900751k. PubMed PMID: 20491501.
3: López-Legentil S, Bontemps-Subielos N, Turon X, Banaigs B. Temporal variation in the production of four secondary metabolites in a colonial ascidian. J Chem Ecol. 2006 Sep;32(9):2079-84. Epub 2006 Aug 5. PubMed PMID: 16924427.
4: Townsend NO, Jackson YA. Synthesis of 9-methyl-1H-[1,4]thiazino[3,2-g]quinoline-2,5,10(3H)-trione, the B,C,D ring core of the shermilamine alkaloids. Org Biomol Chem. 2003 Oct 21;1(20):3557-63. PubMed PMID: 14599017.
5: Delfourne E, Bastide J. Marine pyridoacridine alkaloids and synthetic analogues as antitumor agents. Med Res Rev. 2003 Mar;23(2):234-52. Review. PubMed PMID: 12500290.
6: Koren-Goldshlager G, Aknin M, Kashman Y. Cycloshermilamine D, a new pyridoacridine from the marine tunicate cystodytes violatinctus. J Nat Prod. 2000 Jun;63(6):830-1. PubMed PMID: 10869211.
7: McDonald LA, Eldredge GS, Barrows LR, Ireland CM. Inhibition of topoisomerase II catalytic activity by pyridoacridine alkaloids from a Cystodytes sp. ascidian: a mechanism for the apparent intercalator-induced inhibition of topoisomerase II. J Med Chem. 1994 Oct 28;37(22):3819-27. PubMed PMID: 7525959.
