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2-Iminobiotin (Synonyms: Guanidinobiotin)

Catalog No.GC16664

iNOS and nNOS inhibitor

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2-Iminobiotin Chemical Structure

Cas No.: 13395-35-2

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50mg
$73.00
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100mg
$123.00
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Sample solution is provided at 25 µL, 10mM.

Description of 2-Iminobiotin

2-Iminobiotin is a novel, potent, selective inhibitor of neuronal and inducible nitric oxide synthase.

Nitric oxide synthases (NOS) are a family of enzymes catalyzing the five-electron oxidation of L-arginine to citrulline and nitric oxide. NO produced by NOS is an important cellular signaling molecule implicated in modulating vascular tone, airway tone, insulin secretion, and peristalsis, angiogenesis and neural development [2].

In vitro: 2-Iminobiotin is a reversible inhibitor of murine iNOS and rat n-cNOS with the Ki values of 21.8 and 37.5 μM, respectively. The guanidino group of 2-iminobiotin is essential for binding. 2-iminobiotin carboxy derivatives were also inhibitors of iNOS which indicates that the free carboxyl group is not required for binding.

In vivo: A dose of 30 mg/kg per day of 2-iminobiotin after hypoxia-ischemia resulted in significant long-term neuro-protection [3]. 2-iminobiotin (2-IB) reduced hypoxia-ischemia (HI)-induced brain damage in neonatal rats. In P7 rat pups, 2-Iminobiotin treatment reduced long-term brain damage in female but not male rats [4].

References:
[1] Sup S J, Green B G, Grant S K.  2-Iminobiotin is an inhibitor of nitric oxide synthases[J]. Biochemical and biophysical research communications, 1994, 204(2): 962-968.
[2] Moncada S, Palmer R M L, Higgs E A.  Nitric oxide: physiology, pathophysiology, and pharmacology[J]. Pharmacological reviews, 1991, 43(2): 109-142.
[3] Tweel E R W, van Bel F, Kavelaars A, et al.  Long-term neuroprotection with 2-iminobiotin, an inhibitor of neuronal and inducible nitric oxide synthase, after cerebral hypoxia-ischemia in neonatal rats[J]. Journal of Cerebral Blood Flow & Metabolism, 2005, 25(1): 67-74.
[4] Nijboer C H A, Groenendaal F, Kavelaars A, et al.  Gender-Specific Neuroprotection by 2-Iminobiotin after Hypoxia—Ischemia in the Neonatal Rat via a Nitric Oxide Independent Pathway[J]. Journal of Cerebral Blood Flow & Metabolism, 2007, 27(2): 282-292.

Chemical Properties of 2-Iminobiotin

Cas No. 13395-35-2 SDF
Synonyms Guanidinobiotin
Chemical Name (3aR,6S,6aS)-2-amino-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazole-6-pentanoic acid
Canonical SMILES [H][C@](NC1=N)(CS[C@H]2CCCCC(O)=O)[C@@]2(N1)[H]
Formula C10H17N3O2S M.Wt 243.3
Solubility DMSO : 12.5 mg/mL (51.37 mM; Need ultrasonic) Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of 2-Iminobiotin

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1 mg 5 mg 10 mg
1 mM 4.1102 mL 20.5508 mL 41.1015 mL
5 mM 0.822 mL 4.1102 mL 8.2203 mL
10 mM 0.411 mL 2.0551 mL 4.1102 mL
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