NBD-TMA

NBD-TMA (2-(4-nitro-2,1,3-benzoxadiazol-7-yl)aminoethyl]trimethylammonium) is a small, positively charged (+1) fluorescent dye. It was also known as EAM-1 (N,N,N,-trimethyl-2[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]ethanaminium iodide) when it was briefly supplied by Macrocyclics Company as an iodide complex.

NBD-TMA
Names
Preferred IUPAC name
N,N,N-Trimethyl-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]ethan-1-aminium
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C11H16N5O3/c1-16(2,3)7-6-12-8-4-5-9(15(17)18)11-10(8)13-19-14-11/h4-5,12H,6-7H2,1-3H3/q+1
    Key: CVUNMBFLPVSENX-UHFFFAOYSA-N
  • InChI=1/C11H16N5O3/c1-16(2,3)7-6-12-8-4-5-9(15(17)18)11-10(8)13-19-14-11/h4-5,12H,6-7H2,1-3H3/q+1
    Key: CVUNMBFLPVSENX-UHFFFAOYAY
  • C[N+](C)(C)CCNc1ccc(c2c1non2)[N+](=O)[O-]
Properties
C11H16N5O3+
Molar mass 266.280 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

NBD-TMA has an excitation maximum at 458 nm and an emission maximum at 530 nm. It also has a smaller local excitation maximum around 343 nm. The molar extinction coefficient is about 13,000 cm−1M−1 and its overall effective fluorescence is about 1% that of fluorescein. It is only mildly sensitive to halide ion collision quenching.

NBD-TMA was designed as a probe for monitoring renal transport of organic cations.[1] As a small, positively charged fluorophore, it has also seen use as a tracer for measuring gap junction coupling in cases of cation selective connexin channels.[2]

References
  1. Bednarczyk, D.; Mash, E. A.; Aavula, B. R.; Wright, S. H. (2000). "NBD-TMA: A novel fluorescent substrate of the peritubular organic cation transporter of renal proximal tubules". Pflügers Archiv: European Journal of Physiology. 440 (1): 184–192. doi:10.1007/s004240000283. PMID 10864014. S2CID 2699877.
  2. Zhao, H. B. (2005). "Connexin26 is responsible for anionic molecule permeability in the cochlea for intercellular signalling and metabolic communications". The European Journal of Neuroscience. 21 (7): 1859–1868. doi:10.1111/j.1460-9568.2005.04031.x. PMC 2548270. PMID 15869481.
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