Synonym
MEGA-9; Nonanoyl-N-Methylglucamide
IUPAC/Chemical Name
1-deoxy-1-[methyl(1-oxononyl)amino]-D-glucitol
InChi Key
GCRLIVCNZWDCDE-SJXGUFTOSA-N
InChi Code
InChI=1S/C16H33NO6/c1-3-4-5-6-7-8-9-14(21)17(2)10-12(19)15(22)16(23)13(20)11-18/h12-13,15-16,18-20,22-23H,3-11H2,1-2H3/t12-,13+,15+,16+/m0/s1
SMILES Code
O[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)CN(C)C(CCCCCCCC)=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
Biological target:
MEGA-9 is a nonionic detergent that can be used to solubilize membrane proteins.
In vitro activity:
Self-aggregation of MEGA-9 (N-nonanoyl-N-methyl-D-glucamine), a nonionic sugar-based surfactant, was studied with respect to the effect of salt (NaCl) and ionic liquid (1-butyl-3-methylimidazolium tetrafluoroborate) on its critical micelle concentration (cmc), aggregation number, hydrodynamic dimensions, energetics of micellization, and micellar microenvironment. Density functional theory (DFT) calculations showed that the ternary combination MEGA-9/IL/H2O had the maximum interaction energy compared to any of the binary combinations.
Reference: J Phys Chem B. 2013 Jun 27;117(25):7578-92. https://pubmed.ncbi.nlm.nih.gov/23718221/
In vivo activity:
The acceptor for Clostridium botulinum type B neurotoxin was solubilized from rat brain synaptic membrane with nonionic detergent, nonanoyl-N-methylglucamide (MEGA-9). The solubilized acceptor was assayed for the binding activity by precipitating the acceptor with acetone in the presence of phosphatidylcholine.
Reference: Biochim Biophys Acta. 1993 Nov 28;1158(3):333-8. https://pubmed.ncbi.nlm.nih.gov/8251534/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
89.43 |
| DMSO |
30.0 |
89.43 |
| DMSO:PBS (pH 7.2) (1:2) |
0.3 |
0.98 |
| Ethanol |
1.0 |
2.98 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
335.44
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. Pan A, Mati SS, Naskar B, Bhattacharya SC, Moulik SP. Self-aggregation of MEGA-9 (N-nonanoyl-N-methyl-D-glucamine) in aqueous medium: physicochemistry of interfacial and solution behaviors with special reference to formation energetics and micelle microenvironment. J Phys Chem B. 2013 Jun 27;117(25):7578-92. doi: 10.1021/jp400139d. Epub 2013 Jun 12. PMID: 23718221.
2. Luescher IF, Unanue ER. Purification and photoaffinity labeling of the I-Ak histocompatibility molecule. J Immunol Methods. 1990 Dec 31;135(1-2):233-45. doi: 10.1016/0022-1759(90)90277-3. PMID: 2177076.
3. Nishiki T, Ogasawara J, Kamata Y, Kozaki S. Solubilization and characterization of the acceptor for Clostridium botulinum type B neurotoxin from rat brain synaptic membranes. Biochim Biophys Acta. 1993 Nov 28;1158(3):333-8. doi: 10.1016/0304-4165(93)90032-4. PMID: 8251534.
In vitro protocol:
1. Pan A, Mati SS, Naskar B, Bhattacharya SC, Moulik SP. Self-aggregation of MEGA-9 (N-nonanoyl-N-methyl-D-glucamine) in aqueous medium: physicochemistry of interfacial and solution behaviors with special reference to formation energetics and micelle microenvironment. J Phys Chem B. 2013 Jun 27;117(25):7578-92. doi: 10.1021/jp400139d. Epub 2013 Jun 12. PMID: 23718221.
2. Luescher IF, Unanue ER. Purification and photoaffinity labeling of the I-Ak histocompatibility molecule. J Immunol Methods. 1990 Dec 31;135(1-2):233-45. doi: 10.1016/0022-1759(90)90277-3. PMID: 2177076.
In vivo protocol:
1. Nishiki T, Ogasawara J, Kamata Y, Kozaki S. Solubilization and characterization of the acceptor for Clostridium botulinum type B neurotoxin from rat brain synaptic membranes. Biochim Biophys Acta. 1993 Nov 28;1158(3):333-8. doi: 10.1016/0304-4165(93)90032-4. PMID: 8251534.
1. Hildreth, J.E.K. N-D-Gluco-N-methylalkanamide compounds, a new class of non-ionic detergents for membrane biochemistry. Biochem. J. 207(2), 363-366 (1982).
2. Miyagishi, S., Okada, K., and Asakawa, T. Salt effect on critical micelle concentrations of nonionic surfactants, N-acyl-N-methylglucamides (MEGA-n). J. Colloid. Interface Sci. 238(1), 91-95 (2001).
3. Hanatani, M., Nishifuji, K., Futai, M., et al. Solubilization and reconstitution of membrane proteins of Escherichia coli using alkanoyl-N-methylglucamides. J. Biochem. 95(5), 1349-1353 (1984).
