2-Iminobiotin (hydrobromide)

2-Iminobiotin is a guanidine-modified derivative of the carboxylase coenzyme biotin (Item No. 22582) and an inhibitor of inducible nitric oxide synthase (iNOS) and neuronal NOS (nNOS; K_is = 21.8 and 37.5 µM for the mouse and rat enzymes, respectively).¹ It has been used to label and selectively retrieve sialoglycoproteins from erythrocyte ghosts.² 2-Iminobiotin (0.2 mg/kg every four hours) prevents hypoxia-ischemia-induced decreases in brain phosphocreatine and ATP levels and increases in edema in the parietal cortex and striatum, as well as reduces apoptosis in the parietal- and temporal cortex and striatum, in piglets.³ It increases survival of, and decreases electrographic seizures in, hypoxia-ischemia-injured piglets when administered at doses of 0.2 and 1 mg/kg every four hours.⁴ Lipid nanoparticles (LNPs) containing 2-iminobiotin conjugated to poly-L-lysine have been used to improve LNP tumor targeting, uptake, and retention compared with LNPs containing biotin conjugated to poly-L-lysine in rats.⁵

WARNING This product is not for human or veterinary use.

1. Sup, S.J., Green, B.G., and Grant, S.K. 2-Iminobiotin is an inhibitor of nitric oxide synthases. Biochem. Biophys. Res. Commun. 204(2), (1994).

2. Orr, G.A. The use of the 2-iminobiotin-avidin interaction for the selective retrieval of labeled plasma membrane components. The Journal of Biological Chemisty 256(2), 761-766 (1981).

3. Peeters-Scholte, C., Koster, J., Veldhuis, W., et al. Neuroprotection by selective nitric oxide synthase inhibition at 24 hours after perinatal hypoxia-ischemia. Stroke 33(9), 2304-2310 (2002).

4. Bjorkman, S.T., Ireland, Z., Fan, X., et al. Short-term dose-response characteristics of 2-iminobiotin immediately postinsult in the neonatal piglet after hypoxia-ischemia. Stroke 44(3), 809-811 (2013).

5. Poon, Z., Chang, D., Zhao, X., et al. Layer-by-layer nanoparticles with a pH-sheddable layer for in vivo targeting of tumor hypoxia. ACS Nano 5(6), 4284-4292 (2011).