748110

SF₇-AM

95% (HPLC)

• Synonym(s): SF₇-AM, Bis(acetoxymethyl)
• Empirical Formula (Hill Notation): C₃₁H₂₃N₇O₁₂
• CAS Number: 1416872-50-8
• Molecular Weight: 685.55
• UNSPSC Code: 12352200
• PubChem Substance ID: 329765872

Properties

• assay: 95% (HPLC)
• mp: 160-165 °C
• storage temp.: −20°C
• SMILES string: CC(OCOC(CN(CC(OCOC(C)=O)=O)C(C1=CC=C(C(OC23C4=C(C=C(N=[N+]=[N-])C=C4)OC5C2C=CC(N=[N+]=[N-])=C5)=O)C3=C1)=O)=O)=O
• InChI: 1S/C31H25N7O12/c1-16(39)45-14-47-27(41)12-38(13-28(42)48-15-46-17(2)40)29(43)18-3-6-21-24(9-18)31(50-30(21)44)22-7-4-19(34-36-32)10-25(22)49-26-11-20(35-37-33)5-8-23(26)31/h3-11,22,25H,12-15H2,1-2H3
• InChI key: KVUJKFQKNGAJST-UHFFFAOYSA-N

Description

Application

SF₇-AM is a fluorogenic; or "caged" rhodamine 110 derivative for the detection of hydrogen sulfide (H₂S). Upon exposure to H₂S; the azide functional groups are reduced to primary amines; restoring the fluorescence of the "caged" fluorophore. A fluorescence intensity increase of 20x is observed upon 1h of SF₇-AM exposure to H₂S. This activation of SF₇-AM has been shown to detect H₂S levels as low as 500 nM in vitro. SF₇-AM has also been engineered specifically for use in live cell imaging of H₂S through the addition of the acetoxymethyl ester groups; which are cleaved in vivo by esterases. This results in adding a net -2 charge to the probe; which was demonstrated to "trap" the probe in cells; thus increasing the sensitivity of the probe even when the cell culture media was changed.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable