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Documentos Principais

748110

Sigma-Aldrich

SF7-AM

95% (HPLC)

Sinônimo(s):

SF7-AM, Bis(acetoxymethyl)

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About This Item

Fórmula empírica (Notação de Hill):
C31H23N7O12
Número CAS:
Peso molecular:
685.55
Código UNSPSC:
12352200
ID de substância PubChem:

Ensaio

95% (HPLC)

pf

160-165 °C

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

KVUJKFQKNGAJST-UHFFFAOYSA-N

Aplicação

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.

Pictogramas

Exclamation mark

Palavra indicadora

Warning

Frases de perigo

Classificações de perigo

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable


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Cell-trappable fluorescent probes for endogenous hydrogen sulfide signaling and imaging H2O2-dependent H2S production.
Lin Vs, et al.
Proceedings of the National Academy of Sciences of the USA, 110(18), 7131?7135-7131?7135 null
Hang Zou et al.
Molecular plant-microbe interactions : MPMI, 32(8), 972-985 (2019-06-18)
The rhizobium-legume symbiotic system is crucial for nitrogen cycle balance in agriculture. Hydrogen sulfide (H2S), a gaseous signaling molecule, may regulate various physiological processes in plants. However, whether H2S has regulatory effect in this symbiotic system remains unknown. Herein, we

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