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DTSSP (3,3′-dithiobis(sulfosuccinimidyl propionate))

Name: DTSSP (3,3′-dithiobis(sulfosuccinimidyl propionate))
Brand: ALDRICH

Synonym(s):

DTSSP, bis(sulfosuccinimidyl) 3,3′-dithiobis(propionate)

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About This Item

Empirical Formula (Hill Notation):

C₁₄H₁₄N₂O₁₄S₄Na₂

CAS Number:

81069-02-5

Molecular Weight:

608.51

MDL number:

MFCD00054980

UNSPSC Code:

12352108

PubChem Substance ID:

329768788

NACRES:

NA.22

Assay

≥80%

Quality Level

100

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

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

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

InChI key

XRWWBWZHHSXBNC-UHFFFAOYSA-L

Related Categories

Crosslinkers

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

Caution

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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