Seminaphtharhodafluor

Seminaphtharhodafluor or SNARF is a fluorescent dye that changes color with pH. It can be used to construct optical biosensors that use enzymes that change pH.

Seminaphtharhodafluor
Names
Other names
Seminaphtharhodafluorescein; Seminaphthorhodafluor
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C24H15NO4/c25-14-6-10-19-21(12-14)28-22-16-8-7-15(26)11-13(16)5-9-20(22)24(19)18-4-2-1-3-17(18)23(27)29-24/h1-12,26H,25H2
    Key: DYPYMMHZGRPOCK-UHFFFAOYSA-N
  • O=C(O1)C2=C(C=CC=C2)C31C4=CC=C(N)C=C4OC5=C3C=CC6=C5C=CC(O)=C6
Properties
C24H15NO4
Molar mass 381.387 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The absorption peak of the derivative carboxy-SNARF at pH 6.0 is at wavelength (515 and) 550 nm, while that at pH 9.0 is at 575 nm.

The emission peak of carboxy-SNARF at pH 6.0 is at wavelength 585 nm, while that at pH 9.0 is at 640 nm.[1]

SNARF-1 can serve as a substrate for the MRP1 (multidrug resistance-associated protein-1) drug transporter, to measure the activity of the MRP1 transporter. For this purpose, an acetomethoxyester group is added to SNARF-1. Cellular esterases cleave off SNARF-1, and its transport out of the cells can be measured by following the loss of fluorescence from the cells.[2]

References
  1. "5-(and-6)-Carboxy SNARF™-1". www.thermofisher.com.
  2. Weekes, M. P.; Tan, S. Y. L.; Poole, E.; Talbot, S.; Antrobus, R.; Smith, D. L.; Montag, C.; Gygi, S. P.; Sinclair, J. H.; Lehner, P. J. (12 April 2013). "Latency-Associated Degradation of the MRP1 Drug Transporter During Latent Human Cytomegalovirus Infection". Science. 340 (6129): 199–202. Bibcode:2013Sci...340..199W. doi:10.1126/science.1235047. PMC 3683642. PMID 23580527.


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