803200
DTSSP (3,3′-dithiobis(sulfosuccinimidyl propionate))
Synonym(s):
DTSSP, bis(sulfosuccinimidyl) 3,3′-dithiobis(propionate)
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About This Item
Empirical Formula (Hill Notation):
C14H14N2O14S4Na2
CAS Number:
Molecular Weight:
608.51
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352108
MDL number:
InChI
1S/C14H16N2O14S4.2Na/c17-9-5-7(33(23,24)25)13(21)15(9)29-11(19)1-3-31-32-4-2-12(20)30-16-10(18)6-8(14(16)22)34(26,27)28;;/h7-8H,1-6H2,(H,23,24,25)(H,26,27,28);;/q;2*+1/p-2
SMILES string
O=C(CC1S(=O)([O-])=O)N(OC(CCSSCCC(ON2C(CC(S(=O)([O-])=O)C2=O)=O)=O)=O)C1=O.[Na+].[Na+]
InChI key
XRWWBWZHHSXBNC-UHFFFAOYSA-L
assay
≥80%
form
powder
mol wt
608.51
reaction suitability
reagent type: cross-linking reagent
storage condition
desiccated
solubility
soluble (>6mg/ml in water)
shipped in
ambient
storage temp.
2-8°C
Quality Level
Related Categories
General description
DTSSP is 3,3′-Dithiobis(sulfosuccinimidylpropionate), which contains an amine-reactive N-hydroxysulfosuccinimide (sulfo-NHS) ester at each end of an 8-carbon spacer arm. Sulfo-NHS esters react with primary amines at pH 7-9 to form stable amide bonds, along with release of the N-hydroxysulfosuccinimide leaving group. Proteins, including antibodies, generally have several primary amines in the side chain of lysine (K) residues and the N-terminus of each polypeptide that are available as targets for sulfo-NHS-ester crosslinking reagents. DSS, the non-sulfonated analog of DTSSP is also available for applications that require a membrane-permeable crosslinker.
Application
- Enhancing Ocular Antisense Oligonucleotide Delivery: Utilizing Cowpea Chlorotic Mottle Virus-like particles, this study incorporates DTSSP for the enhancement of antisense oligonucleotide delivery targeting posterior segment ocular diseases, demonstrating a novel approach in biocompatible drug delivery systems (Pretto et al., 2021).
- Regulation of Integrin-Tetraspanin Interactions: DTSSP is utilized to stabilize interactions between integrins and the tetraspanin CD9, providing critical insights into cell adhesion and signaling mechanisms, relevant to cancer and other pathologies (Torres-Gómez et al., 2021).
- Gene Delivery Platform Development: A study on adeno-associated viral vectors employs DTSSP for cross-linking to tune cellular tropisms and enhance gene delivery, showing potential for targeted gene therapy applications (Yoo et al., 2020).
- Protein Interactor Identification: DTSSP is instrumental in identifying interactors of the Arabidopsis thaliana Plant Natriuretic Peptide (AtPNP-A) using mass spectrometry, aiding in the understanding of plant signaling pathways (Turek et al., 2020).
- Protein Delivery via Nanoparticles: Research on poly(l-lysine)-grafted-poly(ethylene glycol) nanoparticles highlights the use of DTSSP for redox-responsive crosslinking, improving the delivery mechanisms for therapeutic proteins (Seaberg et al., 2020).
Features and Benefits
- Reactive groups: sulfo-NHS ester (both ends)
- Reactive towards: amino groups (primary amines)
- Sulfo-NHS ester reacts rapidly with any primary amine-containing molecule
- Disulfide bond in the spacer arm is readily cleaved by 10-50 mM DTT or TCEP at pH 8.5
- Spacer arm also easily cleaved with reducing SDS-PAGE sample loading
- Cleavable crosslinker allows separation of crosslinked products
- Water-soluble; compare with DSP
- Membrane-impermeable, allowing for cell surface labeling
Disclaimer
This product is sensitive to moisture. The vial is packaged in a resealable bag with a desiccant to reduce exposure to moisture. After cold storage, equilibrate the vial to room temperature before opening to reduce condensation inside the vial. Make fresh solutions. Storage of stock solutions is not recommended. After use, return the vial to the resealable bag. Close the bag and store the product at the recommended temperature.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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