Synonym
GMBS Crosslinker; N-(gamma-Maleimidobutyryloxy)succinimide; N-Succinimidyl 4-maleimidobutyrate
IUPAC/Chemical Name
4-Maleimidobutyric acid N-succinimidyl ester
InChi Key
PVGATNRYUYNBHO-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H12N2O6/c15-8-3-4-9(16)13(8)7-1-2-12(19)20-14-10(17)5-6-11(14)18/h3-4H,1-2,5-7H2
SMILES Code
O=C(ON1C(CCC1=O)=O)CCCN2C(C=CC2=O)=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
>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
Biological target:
GMBS is a heterobifunctional cross-linker.
In vitro activity:
Finally, functionalizing OMVs with N-γ-(maleimidobutyryl)oxysuccinimide-ester (GMBS), generating ready-to-conjugate OMVs, did not affect the structural integrity of the OMVs and as such, they could be evaluated with the validated FFF-MALS method.
Reference: Anal Chem. 2022 Sep 6;94(35):12033-12041. https://pubmed.ncbi.nlm.nih.gov/36007249/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
50.0 |
178.42 |
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
280.24
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. van der Put RMF, Spies A, Metz B, Some D, Scherrers R, Pieters R, Danial M. Validation of an FFF-MALS Method to Characterize the Production and Functionalization of Outer-Membrane Vesicles for Conjugate Vaccines. Anal Chem. 2022 Sep 6;94(35):12033-12041. doi: 10.1021/acs.analchem.2c01590. Epub 2022 Aug 25. PMID: 36007249; PMCID: PMC9453738.
2. Svozilová H, Plichta Z, Proks V, Studená R, Baloun J, Doubek M, Pospíšilová Š, Horák D. RGDS-Modified Superporous Poly(2-Hydroxyethyl Methacrylate)-Based Scaffolds as 3D In Vitro Leukemia Model. Int J Mol Sci. 2021 Feb 27;22(5):2376. doi: 10.3390/ijms22052376. PMID: 33673496; PMCID: PMC7956824.
In vitro protocol:
1. van der Put RMF, Spies A, Metz B, Some D, Scherrers R, Pieters R, Danial M. Validation of an FFF-MALS Method to Characterize the Production and Functionalization of Outer-Membrane Vesicles for Conjugate Vaccines. Anal Chem. 2022 Sep 6;94(35):12033-12041. doi: 10.1021/acs.analchem.2c01590. Epub 2022 Aug 25. PMID: 36007249; PMCID: PMC9453738.
2. Svozilová H, Plichta Z, Proks V, Studená R, Baloun J, Doubek M, Pospíšilová Š, Horák D. RGDS-Modified Superporous Poly(2-Hydroxyethyl Methacrylate)-Based Scaffolds as 3D In Vitro Leukemia Model. Int J Mol Sci. 2021 Feb 27;22(5):2376. doi: 10.3390/ijms22052376. PMID: 33673496; PMCID: PMC7956824.
1: Nadeau OW, Anderson DW, Yang Q, Artigues A, Paschall JE, Wyckoff GJ, McClintock JL, Carlson GM. Evidence for the location of the allosteric activation switch in the multisubunit phosphorylase kinase complex from mass spectrometric identification of chemically crosslinked peptides. J Mol Biol. 2007 Feb 2;365(5):1429-45. Epub 2006 Oct 21. PubMed PMID: 17123541; PubMed Central PMCID: PMC1852525.
2: Danczyk R, Krieder B, North A, Webster T, HogenEsch H, Rundell A. Comparison of antibody functionality using different immobilization methods. Biotechnol Bioeng. 2003 Oct 20;84(2):215-23. PubMed PMID: 12966578.
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4: Myers DE, Uckun FM, Swaim SE, Vallera DA. The effects of aromatic and aliphatic maleimide crosslinkers on anti-CD5 ricin immunotoxins. J Immunol Methods. 1989 Jul 6;121(1):129-42. PubMed PMID: 2474026.
