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MAL-dPEG®₈-acid (QBD-10275)

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Description

MAL-dPEG®8-acid, product number QBD-10275, is a crosslinker that joins sulfhydryl groups to free amines through a single molecular weight polyethylene glycol (PEG) chain of discrete length. The maleimidopropyl moiety reacts with sulfhydryl groups via a Michael addition reaction. The propionic acid terminus of the molecule reacts directly with free amines using EDC or another carbodiimide to form amide bonds. Alternatively, activation of the propionic acid group with N-hydroxysuccinimide (NHS), 2,3,5,6-tetrafluorophenol (TFP), or some other acylating agent permits amide bond formation under mild, controlled conditions.

Chemical couplings between free amines and free thiols are among the most popular, most useful crosslinking reactions in bioconjugate chemistry. These syntheses require heterobifunctional reagents that bridge the two groups. While traditional crosslinkers are hydrophobic molecules, Vector Laboratories’ crosslinking products are water-soluble, amphiphilic, single molecular weight PEG compounds with discrete chain lengths, hence the dPEG® tradename under which we sell them. Almost inevitably, the conjugation of conventional hydrophobic crosslinking reagents to biomolecules triggers problems such as aggregation and precipitation of the conjugates. Conversely, these problems do not occur with our water-soluble, non-immunogenic dPEG® crosslinkers.

The reaction of the maleimide end of MAL-dPEG®8-acid with a sulfhydryl proceeds optimally at pH 6.5 – 7.5. Use the lowest reasonable pH within this range. Above pH 7.5, free amines compete with free thiols at the maleimide reaction site, which can cause confusing results. Moreover, at higher pH values, the maleimide ring may open to form unreactive maleamic acid.

After the maleimide end of the molecule reacts with a sulfhydryl, the terminal propionic acid group may be left unreacted for charge modification or the conjugate or activated with an acylating agent such as NHS or TFP. The active ester then reacts with free amines to complete the crosslink.

MAL-dPEG®8-acid, product number QBD-10275, has been published in numerous patents and a few papers. The more notable published works involve the development of antibody-drug conjugates (ADCs). Other possible uses for this product include the following:
crosslinking proteins to hydrogels;
development of imaging applications;
development of immunoassays; and,
surface coating of nanoparticles.

Specifications

Unit Size100 mg, 1000 mg
Molecular Weight592.63; single compound
Chemical formulaC₂₆H₄₄N₂O₁₃
CAS1334177-86-4
Purity> 98%
SpacersdPEG® Spacer is 34 atoms and 38.8 Å
ShippingAmbient
Typical solubility properties (for additional information contact Customer Support)Methylene chloride, Acetonitrile, DMAC or DMSO.
Storage and handling-20°C; Always let come to room temperature before opening; be careful to limit exposure to moisture and restore under an inert atmosphere; stock solutions can be prepared with dry solvent and kept for several days (freeze when not in use). dPEG® pegylation compounds are generally hygroscopic and should be treated as such. This will be less noticeable with liquids, but the solids will become tacky and difficult to manipulate, if care is not taken to minimize air exposure.

References

Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0); See pp. 276-335 for general description and use of heterobifunctional crosslinkers, and the specific sample protocol for SMCC or sulfo-SMCC on pp. 283-286.

Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See Chapter 18, Discrete PEG Reagents, pp. 787-821, for a full overview of the dPEG® products.

Post-transcriptional regulation of the GASC1 oncogene with active tumor-targeted siRNA-nanoparticle. Sara Movassaghian, Claudia Hildebrandt, Yuran Xie, Rayna Rosati, Ying Li, Na Hyung Kim, Denise Conti, Sandro RP da Rocha, Zeng-Quan Yang, and Olivia M. Merkel. Molecular Pharmaceutics. 2016, May 25, 2016. DOI: 10.1021/acs.molpharmaceut.5b00948.

Applicable patents and legal notices are available at legal notices.

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