All Photos(1)
Synonym(s):
1,2-Bis(2-maleimidoethoxy)ethane, 1,8-Bis(maleimido)-3,6-dioxaoctane
Empirical Formula (Hill Notation):
C14H16N2O6
CAS Number:
Molecular Weight:
308.29
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22
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![2-[8-(3-Hexyl-2,6-dioctylcyclohexyl)octyl]pyromellitic diimide oligomer, maleimide terminated, lower viscosity](/deepweb/assets/sigmaaldrich/product/structures/328/686/6540396c-3358-4bfb-9ca7-7020672b916c/640/6540396c-3358-4bfb-9ca7-7020672b916c.png)
Assay
≥90%
form
powder
mol wt
308.29
reaction suitability
reagent type: cross-linking reagent
storage condition
desiccated
solubility
water: soluble
shipped in
ambient
storage temp.
2-8°C
SMILES string
O=C(C=CC1=O)N1CCOCCOCCN2C(C=CC2=O)=O
InChI
1S/C14H16N2O6/c17-11-1-2-12(18)15(11)5-7-21-9-10-22-8-6-16-13(19)3-4-14(16)20/h1-4H,5-10H2
InChI key
FERLGYOHRKHQJP-UHFFFAOYSA-N
General description
BM(PEG)2 and BM(PEG)3 are homobifunctional, maleimide crosslinkers for conjugation between sulfhydryl groups (-SH). Such bismaleimide crosslinkers are commonly used to explore and characterize protein structure (i.e. oligomerization) or protein interactions. Because BM(PEG)2 and BM(PEG)3 have the same reactivity but differ in length, the relative success of these and similar reagents in forming crosslinks between sites in a protein oligomer or interaction can assist in determining intra- and intermolecular distances.
Features and Benefits
- Reactive groups: maleimide (both ends)
- Reactive towards: sulfhydryl groups
- Long, pegylated, sulfhydryl-to-sulfhydryl crosslinkers, composed of maleimide groups and 2-unit polyethylene glycol spacer arm
- PEG spacers provide unique advantages, including enhanced solubility, increased stability, reduced tendency toward aggregation and reduced immunogenicity
- Pure compounds with defined structure and molecular weight, ensuring reproducible protein-modification effects
- Ideal for small molecule or peptide conjugations
Caution
This product is sensitive to moisture. The vial is packaged in a resealable bag with a desiccant to reduce exposure to moisture. After cold storage, equilibrate the vial to room temperature before opening to reduce condensation inside the vial. Make fresh solutions. Storage of stock solutions is not recommended. After use, return the vial to the resealable bag. Close the bag and store the product at the recommended temperature.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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Kyoko Takebe et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 17(14), 2037-2047 (2003-11-05)
Epimorphin is a mesenchymal morphogen that has been shown to mediate epithelial-mesenchymal signaling interactions in various organs. We now show that epimorphin functions in hair follicle morphogenesis; using a novel ex vivo organ culture assay, we define a mechanism for
Ching-Jou Lim et al.
Pharmaceutical research, 21(11), 1985-1992 (2004-12-14)
To investigate if the cross-linking of transferrin receptor (TfR) induced by Tf-oligomers alters the endocytosis of receptor-ligand complexes in cultured tumor cells and hence increases intracellular drug release. An average of 3.5 Tf molecules per aggregate were cross-linked either by
Regina B Troyanovsky et al.
Molecular and cellular biology, 23(22), 7965-7972 (2003-10-31)
E-cadherin is a transmembrane protein that mediates Ca(2+)-dependent cell-cell adhesion. To study cadherin-cadherin interactions that may underlie the adhesive process, a recombinant E-cadherin lacking free sulfhydryl groups and its mutants with novel cysteines were expressed in epithelial A-431 cells. These
Beata Jastrzebska et al.
The Journal of biological chemistry, 279(52), 54663-54675 (2004-10-19)
Rhodopsin (Rho) is a G protein-coupled receptor that initiates phototransduction in rod photoreceptors. High expression levels of Rho in the disc membranes of rod outer segments and the propensity of Rho to form higher oligomeric structures are evident from atomic
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