2-Iminobiotin

Names

[ Name ]:
2-Iminobiotin

[Synonym ]:
2izl
Guanidinobiotin Hexahydro-2-imino-1H-thieno[3,4-d]imidazole-4-pentanoic acid
1H-Thieno[3,4-d]imidazole-4-pentanoic acid, 2-amino-3a,4,6,6a-tetrahydro-, (3aS,4S,6aR)-
MFCD00149243
2-Iminobiotin
EINECS 236-308-9
Guanidinobiotin
5-[(3aR,6S,6aS)-2-Amino-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-6-yl]pentanoic acid

Biological Activity

[Description]:

2-Iminobiotin (Guanidinobiotin) is a biotin (vitamin H or B7) analog. 2-Iminobiotin is a reversible nitric oxide synthases inhibitor with Kis of 21.8 and 37.5μM for murine iNOS and rat n-cNOS, respectively[1]. 2-Iminobiotin superimposes on hypothermia protects human neuronal cells from hypoxia-induced cell damage[2].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> NO Synthase

Research Areas >> Neurological Disease

[Target]

Nitric oxide synthases[1]

[References]

[1]. Sup SJ, et al. 2-Iminobiotin is an inhibitor of nitric oxide synthases. Biochem Biophys Res Commun. 1994 Oct 28;204(2):962-8.

[2]. Zitta K, et al. 2-Iminobiotin Superimposed on Hypothermia Protects Human Neuronal Cells from Hypoxia-Induced Cell Damage: An in Vitro Study. Front Pharmacol. 2018 Jan 11;8:971.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
477.3±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₀H₁₇N₃O₂S

[ Molecular Weight ]:
243.326

[ Flash Point ]:
242.5±31.5 °C

[ Exact Mass ]:
243.104141

[ PSA ]:
110.51000

[ LogP ]:
-0.36

[ Vapour Pressure ]:
0.0±2.6 mmHg at 25°C

[ Index of Refraction ]:
1.737

[ Storage condition ]:
2~8°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Articles

Influence of different classes of NO synthase inhibitors in the pig gastric fundus.

Naunyn Schmiedebergs Arch. Pharmacol. 356(4) , 488-94, (1997)

The inhibitory potency of different classes of nitric oxide synthase (NOS) inhibitors (amino acid-based substances, guanidines, isothioureas, imidazoles and indazoles) versus peripheral neuronal NOS i...

Intermolecular forces and energies between ligands and receptors.

Science 266(5183) , 257-9, (1994)

The recognition mechanisms and dissociation pathways of the avidin-biotin complex and of actin monomers in actin filaments were investigated. The unbinding forces of discrete complexes of avidin or st...

Effects of selective nitric oxide synthase inhibition on IGF-1, caspases and cytokines in a newborn piglet model of perinatal hypoxia-ischaemia.

Dev. Neurosci. 24(5) , 396-404, (2002)

Selective inhibition of neuronal and inducible nitric oxide synthase (NOS) with 2-iminobiotin previously showed a reduction in brain cell injury. In the present study, we investigated the effects of 2...