NBD-TMA

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)	Interactive image;
ChemSpider	21106456;
PubChem CID	53742778;
	InChI 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;
	SMILES C[N+](C)(C)CCNc1ccc(c2c1non2)[N+](=O)[O-];
Properties
Chemical formula	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 (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 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

^ 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.
^ 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.

[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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