Synonym
DSG Crosslinker; Disuccinimidyl glutarate; Di(N-succinimidyl) glutarate
IUPAC/Chemical Name
bis(2,5-dioxopyrrolidin-1-yl) pentanedioate
InChi Key
LNQHREYHFRFJAU-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H14N2O8/c16-8-4-5-9(17)14(8)22-12(20)2-1-3-13(21)23-15-10(18)6-7-11(15)19/h1-7H2
SMILES Code
O=C(ON1C(CCC1=O)=O)CCCC(ON2C(CCC2=O)=O)=O
Purity
>95% (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
More Info
DSG crosslinking takes place through amine-reactive NHS esters at both ends of a 5-atom (7.7 angstrom) spacer arm. DSG crosslinker must be dissolved in an organic solvent, such as DMSO or DMF, then added to an aqueous crosslinking reaction. The directly water soluble version of Di(N-succinimidyl) glutarate (DSG) is BS2G.
Biological target:
DSG Crosslinker is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs).
In vitro activity:
Chemical cross-linking was used to study protein binding interactions between native phospholamban (PLB) and SERCA2a in sarcoplasmic reticulum (SR) vesicles prepared from normal and failed human hearts. Lys(27) of PLB was cross-linked to the Ca(2+) pump at the cytoplasmic extension of M4 (at or near Lys(328)) with the homobifunctional cross-linker, disuccinimidyl glutarate (7.7 Å). Cross-linking was augmented by ATP but abolished by Ca(2+) or thapsigargin, confirming in native SR vesicles that PLB binds preferentially to E2 (low Ca(2+) affinity conformation of the Ca(2+)-ATPase) stabilized by ATP.
Reference: J Biol Chem. 2012 Mar 2;287(10):7582-93. https://pubmed.ncbi.nlm.nih.gov/22247554/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
10.0 |
0.31 |
| DMSO |
60.0 |
183.90 |
| DMSO:PBS (pH 7.2) (1:5) |
0.2 |
0.46 |
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
326.26
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. Akin BL, Jones LR. Characterizing phospholamban to sarco(endo)plasmic reticulum Ca2+-ATPase 2a (SERCA2a) protein binding interactions in human cardiac sarcoplasmic reticulum vesicles using chemical cross-linking. J Biol Chem. 2012 Mar 2;287(10):7582-93. doi: 10.1074/jbc.M111.334987. Epub 2012 Jan 14. Erratum in: J Biol Chem. 2012 May 25;287(22):18586. PMID: 22247554; PMCID: PMC3293560.
2. Malo de Molina P, Le TP, Iturrospe A, Gasser U, Arbe A, Colmenero J, Pomposo JA. Neat Protein Single-Chain Nanoparticles from Partially Denatured BSA. ACS Omega. 2022 Nov 9;7(46):42163-42169. doi: 10.1021/acsomega.2c04805. PMID: 36440132; PMCID: PMC9685756.
In vitro protocol:
1. Akin BL, Jones LR. Characterizing phospholamban to sarco(endo)plasmic reticulum Ca2+-ATPase 2a (SERCA2a) protein binding interactions in human cardiac sarcoplasmic reticulum vesicles using chemical cross-linking. J Biol Chem. 2012 Mar 2;287(10):7582-93. doi: 10.1074/jbc.M111.334987. Epub 2012 Jan 14. Erratum in: J Biol Chem. 2012 May 25;287(22):18586. PMID: 22247554; PMCID: PMC3293560.
2. Malo de Molina P, Le TP, Iturrospe A, Gasser U, Arbe A, Colmenero J, Pomposo JA. Neat Protein Single-Chain Nanoparticles from Partially Denatured BSA. ACS Omega. 2022 Nov 9;7(46):42163-42169. doi: 10.1021/acsomega.2c04805. PMID: 36440132; PMCID: PMC9685756.
1: Spindler V, Rötzer V, Dehner C, Kempf B, Gliem M, Radeva M, Hartlieb E, Harms GS, Schmidt E, Waschke J. Peptide-mediated desmoglein 3 crosslinking prevents pemphigus vulgaris autoantibody-induced skin blistering. J Clin Invest. 2013 Feb;123(2):800-11. doi: 10.1172/JCI60139. Epub 2013 Jan 9. PubMed PMID: 23298835; PubMed Central PMCID: PMC3561799.
2: Aoki T, Wolle D, Preger-Ben Noon E, Dai Q, Lai EC, Schedl P. Bi-functional cross-linking reagents efficiently capture protein-DNA complexes in Drosophila embryos. Fly (Austin). 2014;8(1):43-51. doi: 10.4161/fly.26805. Epub 2013 Dec 13. PubMed PMID: 24135698; PubMed Central PMCID: PMC3974894.
3: Gaucher SP, Hadi MZ, Young MM. Influence of crosslinker identity and position on gas-phase dissociation of Lys-Lys crosslinked peptides. J Am Soc Mass Spectrom. 2006 Mar;17(3):395-405. Epub 2006 Jan 27. PubMed PMID: 16443364.
4: Pimenova T, Nazabal A, Roschitzki B, Seebacher J, Rinner O, Zenobi R. Epitope mapping on bovine prion protein using chemical cross-linking and mass spectrometry. J Mass Spectrom. 2008 Feb;43(2):185-95. PubMed PMID: 17924399.
5: Huang BX, Kim HY, Dass C. Probing three-dimensional structure of bovine serum albumin by chemical cross-linking and mass spectrometry. J Am Soc Mass Spectrom. 2004 Aug;15(8):1237-47. PubMed PMID: 15276171.
6: Martino M, Tamburro AM. Chemical synthesis of cross-linked poly(KGGVG), an elastin-like biopolymer. Biopolymers. 2001 Jul;59(1):29-37. PubMed PMID: 11343278.
7: Novak P, Young MM, Schoeniger JS, Kruppa GH. A top-down approach to protein structure studies using chemical cross-linking and Fourier transform mass spectrometry. Eur J Mass Spectrom (Chichester). 2003;9(6):623-31. PubMed PMID: 15100473.
