Synonym
DSS Crosslinker; Disuccinimidyl suberate; Di(N-succinimidyl) Suberate; Nhs-SA; DSIS; NSC 340008; NSC340008; NSC-340008
IUPAC/Chemical Name
bis(2,5-dioxopyrrolidin-1-yl) octanedioate
InChi Key
ZWIBGKZDAWNIFC-UHFFFAOYSA-N
InChi Code
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
SMILES Code
O=C(ON1C(CCC1=O)=O)CCCCCCC(ON2C(CCC2=O)=O)=O
Purity
>97% (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
The DSS crosslinking reagent must be dissolved in an organic solvent, such as DMSO or DMF, then added to an aqueous crosslinking reaction.
Biological target:
DSS Crosslinker is a non-cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs).
In vitro activity:
For antibody orientation control, antibody-binding Z-domain-autodisplaying Escherichia coli (E. coli) cells and their outer membrane (OM) were utilized, and a disuccinimidyl crosslinker was employed for covalent antibody binding. To fabricate the regenerable immunoaffinity layer, capture antibodies were bound to autodisplayed Z-domains, and then treated with the crosslinker for chemical fixation to the Z-domains. Various crosslinkers, namely disuccinimidyl glutarate (DSG), disuccinimidyl suberate (DSS) and poly (ethylene glycol)-ylated bis (sulfosuccinimidyl)suberate (BS(PEG)5), were evaluated, and DSS at a concentration of 500 μM was confirmed to be optimal.
Reference: Int J Mol Sci. 2021 Dec 31;23(1):459. https://pubmed.ncbi.nlm.nih.gov/35008883/
In vivo activity:
Result of isoelectric focusing showed that the pl of DSS cross-linked Hb was in the range of 4.6-5.2, similar to that of serum albumin. The safety of DSS cross-linked Hb was favored by animal tests on rats and guinea pigs. Exchange transfusion experiment with DSS cross-linked Hb using rats as a model indicated no pressor effect or other significant side effects.
Reference: Sci China C Life Sci. 2005 Feb;48(1):49-60. https://pubmed.ncbi.nlm.nih.gov/15844357/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
10.0 |
0.27 |
|
| DMSO |
114.7 |
311.30 |
|
| DMSO:PBS (pH 7.2) (1:5) |
0.2 |
0.41 |
|
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
368.34
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. Park JM, Kim MY, Jose J, Park M. Covalently Immobilized Regenerable Immunoaffinity Layer with Orientation-Controlled Antibodies Based on Z-Domain Autodisplay. Int J Mol Sci. 2021 Dec 31;23(1):459. doi: 10.3390/ijms23010459. PMID: 35008883; PMCID: PMC8745110.
2. Chung Y, Kim Y, Yun N, Oh YJ. Dysregulated autophagy is linked to BAX oligomerization and subsequent cytochrome c release in 6-hydroxydopmaine-treated neuronal cells. Biochem Biophys Res Commun. 2021 Apr 9;548:20-26. doi: 10.1016/j.bbrc.2021.02.045. Epub 2021 Feb 22. PMID: 33631669.
3. Huang B, Wang Q, Jiang L, Lu S, Li C, Xu C, Wang C, Zhang E, Zhang X. Shikonin ameliorated mice colitis by inhibiting dimerization and tetramerization of PKM2 in macrophages. Front Pharmacol. 2022 Aug 17;13:926945. doi: 10.3389/fphar.2022.926945. PMID: 36059938; PMCID: PMC9428403.
4. Lu X, Zheng C, Xu Y, Su Z. Disuccinimidyl suberate cross-linked hemoglobin as a novel red blood cell substitute. Sci China C Life Sci. 2005 Feb;48(1):49-60. doi: 10.1360/04yc0014. PMID: 15844357.
In vitro protocol:
1. Park JM, Kim MY, Jose J, Park M. Covalently Immobilized Regenerable Immunoaffinity Layer with Orientation-Controlled Antibodies Based on Z-Domain Autodisplay. Int J Mol Sci. 2021 Dec 31;23(1):459. doi: 10.3390/ijms23010459. PMID: 35008883; PMCID: PMC8745110.
2. Chung Y, Kim Y, Yun N, Oh YJ. Dysregulated autophagy is linked to BAX oligomerization and subsequent cytochrome c release in 6-hydroxydopmaine-treated neuronal cells. Biochem Biophys Res Commun. 2021 Apr 9;548:20-26. doi: 10.1016/j.bbrc.2021.02.045. Epub 2021 Feb 22. PMID: 33631669.
In vivo protocol:
1. Huang B, Wang Q, Jiang L, Lu S, Li C, Xu C, Wang C, Zhang E, Zhang X. Shikonin ameliorated mice colitis by inhibiting dimerization and tetramerization of PKM2 in macrophages. Front Pharmacol. 2022 Aug 17;13:926945. doi: 10.3389/fphar.2022.926945. PMID: 36059938; PMCID: PMC9428403.
2. Lu X, Zheng C, Xu Y, Su Z. Disuccinimidyl suberate cross-linked hemoglobin as a novel red blood cell substitute. Sci China C Life Sci. 2005 Feb;48(1):49-60. doi: 10.1360/04yc0014. PMID: 15844357.
1: Merkley ED, Rysavy S, Kahraman A, Hafen RP, Daggett V, Adkins JN. Distance restraints from crosslinking mass spectrometry: mining a molecular dynamics simulation database to evaluate lysine-lysine distances. Protein Sci. 2014 Jun;23(6):747-59. doi: 10.1002/pro.2458. Epub 2014 Apr 3. PubMed PMID: 24639379; PubMed Central PMCID: PMC4093951.
2: Scurtu F, Zolog O, Iacob B, Silaghi-Dumitrescu R. Hemoglobin-albumin cross-linking with disuccinimidyl suberate (DSS) and/or glutaraldehyde for blood substitutes. Artif Cells Nanomed Biotechnol. 2014 Feb;42(1):13-7. doi: 10.3109/21691401.2012.762652. Epub 2013 Jan 23. PubMed PMID: 23342991.
3: Lima DB, de Lima TB, Balbuena TS, Neves-Ferreira AGC, Barbosa VC, Gozzo FC, Carvalho PC. SIM-XL: A powerful and user-friendly tool for peptide cross-linking analysis. J Proteomics. 2015 Nov 3;129:51-55. doi: 10.1016/j.jprot.2015.01.013. Epub 2015 Jan 29. PubMed PMID: 25638023.
4: Rampler E, Stranzl T, Orban-Nemeth Z, Hollenstein DM, Hudecz O, Schlögelhofer P, Mechtler K. Comprehensive Cross-Linking Mass Spectrometry Reveals Parallel Orientation and Flexible Conformations of Plant HOP2-MND1. J Proteome Res. 2015 Dec 4;14(12):5048-62. doi: 10.1021/acs.jproteome.5b00903. Epub 2015 Nov 18. Erratum in: J Proteome Res. 2016 May 6;15(5):1732. PubMed PMID: 26535604.
5: Koolen HH, Gomes AF, Schwab NV, Eberlin MN, Gozzo FC. Imidate-based cross-linkers for structural proteomics: increased charge of protein and peptide ions and CID and ECD fragmentation studies. J Am Soc Mass Spectrom. 2014 Jul;25(7):1181-91. doi: 10.1007/s13361-014-0900-5. Epub 2014 Apr 30. PubMed PMID: 24781457.
