Synonym
DSP Crosslinker; DTSSP Crosslinker; Lomant's Reagent; Disuccinimido dithiobispropionate; DTSP; DTBSP; NSC 328386; NSC328386; NSC-328386
IUPAC/Chemical Name
(2,5-dioxopyrrolidin-1-yl) 3-[[3-(2,5-dioxopyrrolidin-1-yl)oxy-3-oxopropyl]disulfanyl]propanoate
InChi Key
FXYPGCIGRDZWNR-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H16N2O8S2/c17-9-1-2-10(18)15(9)23-13(21)5-7-25-26-8-6-14(22)24-16-11(19)3-4-12(16)20/h1-8H2
SMILES Code
O=C(ON1C(CCC1=O)=O)CCSSCCC(ON2C(CCC2=O)=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
More Info
DSP crosslinking reagent contains a reducible disulfide (thiol) bond in the spacer arm that make it a good choice for various applications. The disulfide bond may be reduced with TCEP-HCl or DTT to reverse the crosslinked proteins.
DSP crosslinker must be dissolved in an organic solvent, such as DMSO or DMF, then added to an aqueous crosslinking reaction. DSP can be used to crosslink intracellular proteins and is often used for crosslinking in immunoprecipitation (IP), Co-IP and ChIP assays.
Biological target:
DSP Crosslinker is a cleavable ADC linker, used in the synthesis of antibody-drug conjugates (ADCs).
In vitro activity:
This study introduces the method of DSP (dithiobis(succinimidyl propionate))-mediated crosslinking, followed by tandem immunoprecipitation (FLAG and HA tags).
Reference: Bio Protoc. 2022 Aug 5;12(15):e4478. https://pubmed.ncbi.nlm.nih.gov/36082367/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
74.18 |
| DMSO |
53.7 |
132.70 |
| DMSO:PBS (pH 7.2) (1:4) |
0.2 |
0.49 |
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
404.41
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. Akaki K, Mino T, Takeuchi O. DSP-crosslinking and Immunoprecipitation to Isolate Weak Protein Complex. Bio Protoc. 2022 Aug 5;12(15):e4478. doi: 10.21769/BioProtoc.4478. PMID: 36082367; PMCID: PMC9411015.
2. Pretto C, Tang M, Chen M, Xu H, Subrizi A, Urtti A, van Hest JCM. Cowpea Chlorotic Mottle Virus-Like Particles as Potential Platform for Antisense Oligonucleotide Delivery in Posterior Segment Ocular Diseases. Macromol Biosci. 2021 Aug;21(8):e2100095. doi: 10.1002/mabi.202100095. Epub 2021 May 24. PMID: 34031995.
In vitro protocol:
1. Akaki K, Mino T, Takeuchi O. DSP-crosslinking and Immunoprecipitation to Isolate Weak Protein Complex. Bio Protoc. 2022 Aug 5;12(15):e4478. doi: 10.21769/BioProtoc.4478. PMID: 36082367; PMCID: PMC9411015.
2. Pretto C, Tang M, Chen M, Xu H, Subrizi A, Urtti A, van Hest JCM. Cowpea Chlorotic Mottle Virus-Like Particles as Potential Platform for Antisense Oligonucleotide Delivery in Posterior Segment Ocular Diseases. Macromol Biosci. 2021 Aug;21(8):e2100095. doi: 10.1002/mabi.202100095. Epub 2021 May 24. PMID: 34031995.
1: Ruini F, Tonda-Turo C, Chiono V, Ciardelli G. Chitosan membranes for tissue engineering: comparison of different crosslinkers. Biomed Mater. 2015 Nov 3;10(6):065002. doi: 10.1088/1748-6041/10/6/065002. PubMed PMID: 26526195.
2: Fröhlich T, Edinger D, Russ V, Wagner E. Stabilization of polyplexes via polymer crosslinking for efficient siRNA delivery. Eur J Pharm Sci. 2012 Dec 18;47(5):914-20. doi: 10.1016/j.ejps.2012.09.006. Epub 2012 Sep 19. PubMed PMID: 23000380.
3: Zheng Q, Zhang H, Tong L, Wu S, Chen H. Cross-linking electrochemical mass spectrometry for probing protein three-dimensional structures. Anal Chem. 2014 Sep 16;86(18):8983-91. doi: 10.1021/ac501526n. Epub 2014 Sep 4. PubMed PMID: 25141260; PubMed Central PMCID: PMC4165463.
4: 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.
5: Calabrese AN, Wang T, Bowie JH, Pukala TL. Negative ion fragmentations of disulfide-containing cross-linking reagents are competitive with aspartic acid side-chain-induced cleavages. Rapid Commun Mass Spectrom. 2013 Jan 15;27(1):238-48. doi: 10.1002/rcm.6445. PubMed PMID: 23239338.
6: Fregnan F, Ciglieri E, Tos P, Crosio A, Ciardelli G, Ruini F, Tonda-Turo C, Geuna S, Raimondo S. Chitosan crosslinked flat scaffolds for peripheral nerve regeneration. Biomed Mater. 2016 Aug 10;11(4):045010. doi: 10.1088/1748-6041/11/4/045010. PubMed PMID: 27508969.
7: Calabrese AN, Good NJ, Wang T, He J, Bowie JH, Pukala TL. A negative ion mass spectrometry approach to identify cross-linked peptides utilizing characteristic disulfide fragmentations. J Am Soc Mass Spectrom. 2012 Aug;23(8):1364-75. doi: 10.1007/s13361-012-0407-x. Epub 2012 May 30. PubMed PMID: 22644737.
8: 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.
9: Zlatic SA, Ryder PV, Salazar G, Faundez V. Isolation of labile multi-protein complexes by in vivo controlled cellular cross-linking and immuno-magnetic affinity chromatography. J Vis Exp. 2010 Mar 9;(37). pii: 1855. doi: 10.3791/1855. PubMed PMID: 20216526; PubMed Central PMCID: PMC2925877.
