803332
Sulfo-SANPAH (sulfosuccinimidyl 6-(4′-azido-2′-nitrophenylamino)hexanoate)
Synonym(s):
(sulfosuccinimidyl 6-(4′-azido-2′-nitrophenylamino)hexanoate), 1-[[6-[(4-azido-2-nitrophenyl)amino]-1-oxohexyl]oxy]-2,5-dioxo-3-pyrrolidinesulfonic acid monosodium salt, Sulfo-SANPAH
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About This Item
Empirical Formula (Hill Notation):
C16H17O9N6NaS
Molecular Weight:
492.40
UNSPSC Code:
12352102
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
form
powder
Quality Level
mol wt
492.4
reaction suitability
reagent type: cross-linking reagent
storage condition
desiccated
solubility
water: soluble
functional group
azide
shipped in
ambient
storage temp.
−20°C
SMILES string
O=C1CC(S(=O)([O-])=O)C(N1OC(CCCCCNC2=CC=C(N=[N+]=[N-])C=C2[N+]([O-])=O)=O)=O.[Na+]
InChI
1S/C16H18N6O9S.Na/c17-20-19-10-5-6-11(12(8-10)22(26)27)18-7-3-1-2-4-15(24)31-21-14(23)9-13(16(21)25)32(28,29)30;/h5-6,8,13,18H,1-4,7,9H2,(H,28,29,30);/q;+1/p-1
InChI key
XXUXLXCHYVHAOD-UHFFFAOYSA-M
General description
ANB-NOS and Sulfo-SANPAH are heterobifunctional crosslinkers that contain an amine-reactive N-hydroxysuccinimide (NHS) ester and a photoactivatable nitrophenyl azide. NHS esters react efficiently with primary amino groups (-NH2) in pH 7-9 buffers to form stable amide bonds. When exposed to UV light nitrophenyl azides form a nitrene group that can initiate addition reactions with double bonds, insertion into C-H and N-H sites, or subsequent ring expansion to react with a nucleophile (e.g., primary amines).
Application
- Dynamic Control of Cell Adhesion on a Stiffness-Tunable Substrate for Analyzing the Mechanobiology of Collective Cell Migration: This study uses Sulfo-SANPAH for photochemical cross-linking in cell adhesion research (Kamimura et al., 2017).
- Evaluation of L929 fibroblast attachment and proliferation on ArgGlyAspSer (RGDS) immobilized chitosan: This paper investigates the use of Sulfo-SANPAH to enhance fibroblast attachment on chitosan substrates (Karakecili et al., 2016).
Features and Benefits
- Reactive groups: sulfo-NHS ester and nitrophenyl azide
- Reactive towards: amino groups and any nucleophile
- Non-cleavable
- N-Sulfosuccinimidyl-6-(4′-azido-2′-nitrophenylamino) hexanoate
- Optimal photolysis occurs at 320-350 nm; minimizes damage to biomolecules by irradiation
- Water soluble; non-cleavable
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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