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
• Empirical Formula (Hill Notation): C₁₆H₁₇O₉N₆NaS
• Molecular Weight: 492.40
• UNSPSC Code: 12352102
• PubChem Substance ID: 329768797
• NACRES: NA.22

Properties

• form: powder
• Quality Level: 100
• 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

Description

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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H319
• pcodes: P264 - P280 - P305 + P351 + P338 - P337 + P313
• Hazard Classifications: Eye Irrit. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable