Synonym
Motuporamine A; Motuporamine-A;
IUPAC/Chemical Name
N1-(3-(azacyclotridecan-1-yl)propyl)propane-1,3-diamine
InChi Key
AXRQFIIUYLOARV-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H39N3/c19-13-11-14-20-15-12-18-21-16-9-7-5-3-1-2-4-6-8-10-17-21/h20H,1-19H2
SMILES Code
NCCCNCCCN1CCCCCCCCCCCC1
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
>2 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
297.53
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: Borselli D, Blanchet M, Bolla JM, Muth A, Skruber K, Phanstiel O 4th, Brunel JM. Motuporamine Derivatives as Antimicrobial Agents and Antibiotic Enhancers against Resistant Gram-Negative Bacteria. Chembiochem. 2017 Feb 1;18(3):276-283. doi: 10.1002/cbic.201600532. Epub 2017 Jan 18. PMID: 28098416; PMCID: PMC5299527.
2: Weston MH, Nakajima K, Back TG. Tandem conjugate additions and 3-aza-Cope rearrangements of tertiary allyl amines and cyclic alpha-vinylamines with acetylenic sulfones. Applications to simple and iterative ring expansions leading to medium and large-ring nitrogen heterocycles. J Org Chem. 2008 Jun 20;73(12):4630-7. doi: 10.1021/jo800600a. Epub 2008 May 23. PMID: 18498198.
3: Williams DE, Craig KS, Patrick B, McHardy LM, van Soest R, Roberge M, Andersen RJ. Motuporamines, anti-invasion and anti-angiogenic alkaloids from the marine sponge Xestospongia exigua (Kirkpatrick): isolation, structure elucidation, analogue synthesis, and conformational analysis. J Org Chem. 2002 Jan 11;67(1):245-58. doi: 10.1021/jo016101c. PMID: 11777468.
4: Goldring WP, Weiler L. Cytotoxic alkaloids motuporamines A-C: synthesis and structural verification. Org Lett. 1999 Nov 4;1(9):1471-3. doi: 10.1021/ol991029e. Erratum in: Org Lett 1999 Dec 2;1(11):1874. PMID: 10825995.
