disodium 1-({8-[(2,5-dioxo-3-sulfonatopyrrolidin-1-yl)oxy]-8-oxooctanoyl}oxy)-2,5-dioxopyrrolidine-3-sulfonate

• ChemBase ID: 133180
• Molecular Formular: C16H18N2Na2O14S2
• Molecular Mass: 572.42866
• Monoisotopic Mass: 571.99948383
• SMILES: C1C(C(=O)N(C1=O)OC(=O)CCCCCCC(=O)ON1C(=O)CC(C1=O)S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+]
• Canonical SMILES: O=C(ON1C(=O)CC(C1=O)S(=O)(=O)[O-])CCCCCCC(=O)ON1C(=O)CC(C1=O)S(=O)(=O)[O-].[Na+].[Na+]
• InChI: InChI=1S/C16H20N2O14S2.2Na/c19-11-7-9(33(25,26)27)15(23)17(11)31-13(21)5-3-1-2-4-6-14(22)32-18-12(20)8-10(16(18)24)34(28,29)30;;/h9-10H,1-8H2,(H,25,26,27)(H,28,29,30);;/q;2*+1/p-2
• InChIKey: MGJYOHMBGJPESL-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium 1-({8-[(2,5-dioxo-3-sulfonatopyrrolidin-1-yl)oxy]-8-oxooctanoyl}oxy)-2,5-dioxopyrrolidine-3-sulfonate
• IUPAC Traditional name: disodium 1-({8-[(2,5-dioxo-3-sulfonatopyrrolidin-1-yl)oxy]-8-oxooctanoyl}oxy)-2,5-dioxopyrrolidine-3-sulfonate
• Synonyms: BS3; Bis(sulfosuccinimidyl) suberate sodium salt; Suberic acid bis(3-sulfo-N-hydroxysuccinimide ester) sodium salt; 1,1'-[(1,8-Dioxo-1,8-octanediyl)bis(oxy)]bis[2,5-dioxo-3-pyrrolidinesulfonic Acid; Bis(sulfosuccinimidyl) Suberate, Sodium Salt; Suberate Bis(sulfosuccinimidyl) Sodium Salt (~85%)

Database IDs

• CAS Number: 82436-77-9; 127634-19-9
• MDL Number: MFCD00054982
• PubChem SID: 162227457
• PubChem CID: 6097991

CALCULATED PROPERTIES

• Acid pKa: -1.6775275
• H Acceptors: 12
• H Donor: 0
• LogD (pH = 5.5): -6.0345874
• LogD (pH = 7.4): -6.0350165
• Log P: -1.2818122
• Molar Refractivity: 100.7648 cm^3
• Polarizability: 42.755386 Å^3
• Polar Surface Area: 241.76 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble; H2O: soluble10 mg/mL; Water
• Apperance: Off-White Solid; powder
• Melting Point: 210°C dec.

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Room Temperature
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (H-NMR)
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - S5799

Application
Water soluble, homobifunctional cross-linking reagent with amine reactivity. Typically coupled to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5). Useful for preparation of protein-protein, receptor-ligand and hapten carrier molecule conjugates. Incorporates 8-atom linker.

Toronto Research Chemicals - S777500

A water-soluble protein cross-linker for: cross-linking and targeting of mouse erythrocytes, receptor-ligand cross-linking, cross-linking of calveolin proteins, cross-linking of growth factors to proteinase inhibitor, and cross-linking of glass beads to a

REFERENCES

• Wolf, B.B. and Gonias, S.L.: Biochemistry, 33, 11270 (1994)
• Terlecky, S.R., et al.: EMBO J., 14, 3627 (1994)
• Sargiacomo, M., et al.: Proc. Natl. Acad. Sci. USA, 92, 9407 (1994)
• Jordan, J.A., et al.: Biochim. Biophys. Acta, 1291, 27 (1996)