Disuccinimidyl suberate

Disuccinimidyl suberate (DSS) is a biochemical tool used as protein cross-linking agent.

Disuccinimidyl suberate[1]
Names
Preferred IUPAC name
Bis(2,5-dioxopyrrolidin-1-yl) octanedioate
Other names
DSS; Suberic acid bis(N-hydroxysuccinimide ester)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.130.330
  • InChI=1S/C16H20N2O8/c19-11-7-8-12(20)17(11)25-15(23)5-3-1-2-4-6-16(24)26-18-13(21)9-10-14(18)22/h1-10H2 N
    Key: ZWIBGKZDAWNIFC-UHFFFAOYSA-N N
  • C1CC(=O)N(C1=O)OC(=O)CCCCCCC(=O)ON2C(=O)CCC2=O
Properties
C16H20N2O8
Molar mass 368.342 g·mol−1
Appearance Solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

It is a homobifunctional N-hydroxysuccinimide (NHS) ester formed by carbodiimide-activation of carboxylate molecules, with identical reactive groups at either end.[2] This reagent is mainly used to form intramolecular crosslinks and preparation of polymers from monomers. It is ideal for receptor ligand cross-linking.

DSS is reactive towards amine groups (primary amines) at pH 7.0-9.0. It is membrane permeable, therefore permitting intracellular crosslinking, has high purity, is non-cleavable, and is water-insoluble (it must be dissolved in an organic solvent such as DMF or DMSO first.)[3]

See also

Applications
  • Chemical crosslinking of intracellular proteins prior to cell lysis and immunoprecipitation
  • 'Fix' protein interactions to allow identification of weak or transient protein interactions
  • Protein crosslinking to create bioconjugates via single-step reactions
  • Immobilize proteins onto amine-coated surfaces[4]

DSS Cross-linking with Hemoglobin-albumin

Disuccinimidyl suberate's reactivity toward primary amines allows it to serve as a cross-linking agent for proteins, without toxic side-products and forming peptide bonds with the lysine residues in a single step. In a study on blood substitutes, DSS was shown to cross-link Hemoglobin intramolecularly, yielding a relatively stable protein (polymerized Hb or polyHb), whose oxygen affinity was almost halved compared to that of native Hb. This was shown to be reversed when Hemoglobin was copolymerized with bovine serum albumin (BSA), showing very little change in auto-oxidation and oxygen affinity compared to the native Hb.[5]

References
  1. Suberic acid bis(N-hydroxysuccinimide ester) at Sigma-Aldrich
  2. “Crosslinking Reagents Handbook - Thermo Fisher Scientific.” Www.thermoscientific.com/Pierce, Thermo Scientific, https://tools.thermofisher.com/content/sfs/brochures/1602163-Crosslinking-Reagents-Handbook.pdf.
  3. "DSS (disuccinimidyl suberate)". www.thermofisher.com. Retrieved 2022-04-23.
  4. "DSS (disuccinimidyl suberate)". www.thermofisher.com. Retrieved 2022-04-23.
  5. Scurtu, Florina; Zolog, Oana; Iacob, Bianca; Silaghi-Dumitrescu, Radu (2014-02-01). "Hemoglobin–albumin cross-linking with disuccinimidyl suberate (DSS) and/or glutaraldehyde for blood substitutes". Artificial Cells, Nanomedicine, and Biotechnology. 42 (1): 13–17. doi:10.3109/21691401.2012.762652. ISSN 2169-1401.



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