I4632
2-Iminobiotin
≥98% (TLC)
Synonym(s):
Guanidinobiotin, Hexahydro-2-imino-1H-thieno[3,4-d]imidazole-4-pentanoic acid
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About This Item
Empirical Formula (Hill Notation):
C10H17N3O2S
CAS Number:
Molecular Weight:
243.33
UNSPSC Code:
12352203
NACRES:
NA.46
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
18952
InChI
1S/C10H17N3O2S/c11-10-12-6-5-16-7(9(6)13-10)3-1-2-4-8(14)15/h6-7,9H,1-5H2,(H,14,15)(H3,11,12,13)/t6-,7-,9-/m0/s1
SMILES string
[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=N)N2
InChI key
WWVANQJRLPIHNS-ZKWXMUAHSA-N
biological source
synthetic (organic)
assay
≥98% (TLC)
form
powder
solubility
1 M HCl: 50 mg/mL, clear, colorless
storage temp.
2-8°C
Quality Level
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Application
2-Iminobiotin has been used as a competitive inhibitor to bind to biotic binding sites on streptavidin in order to restore fluorescence signal.
Disclaimer
Unless otherwise stated in our catalog or other company documentation accompanying the product(s), our products are intended for research use only and are not to be used for any other purpose, which includes but is not limited to, unauthorized commercial uses, in vitro diagnostic uses, ex vivo or in vivo therapeutic uses or any type of consumption or application to humans or animals.
General description
2-Iminobiotin is a cyclic guanidino analog of biotin that has high affinity for avidin at high pH (>9) and low affinity at low pH (<6). The proteins that are iminobiotinylated are selectively contained within the avidin column at pH 9 to 11 and may be eluted at pH 4 or by the addition of biotin. This technique may be very useful in the study of cell surface proteins by labeling and selectively recovering the components that are periodate-sensitive from intact human erythrocyte surface. 2-Iminobiotin reversibly inhibits NOS (nitric oxide synthases) via its guanidino group. It inhibits NO biosynthesis and may be important to understand the binding-site interactions for this important class of enzymes. NOS oxidizes the guanidino-nitrogen of L-arginine to produce nitric oxide and L-citrulline.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Hiroyuki Inoue et al.
Langmuir : the ACS journal of surfaces and colloids, 21(18), 8354-8359 (2005-08-24)
Layered thin films composed of avidin and 2-iminobiotin-labeled poly(ethyleneimine) (ib-PEI) were prepared by a layer-by-layer deposition of avidin and ib-PEI on a solid surface, and the disintegration induced by changing environmental pH and adding biotin in the solution was studied.
F Garret-Flaudy et al.
Biotechnology and bioengineering, 71(3), 223-234 (2001-04-06)
Affinity precipitation, especially secondary effect affinity precipitation, has repeatedly been suggested as a valuable technique for the biotechnical downstream process. The present lack of applications is related to the scarcity of predictable affinity macroligands and to the fact that rather
Amesh B Patel et al.
Journal of the American Chemical Society, 126(5), 1318-1319 (2004-02-05)
The strength of a multimolecular system depends on the number of interactions that hold it together. Using dynamic force spectroscopy, we show how the kinetic stability of a system decreases as the number of molecular bonds is increased, as predicted
Cora H A Nijboer et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 27(2), 282-292 (2006-06-01)
We have shown earlier that 2-iminobiotin (2-IB) reduces hypoxia-ischemia (HI)-induced brain damage in neonatal rats, and presumed that inhibition of nitric oxide synthases (NOS) was the underlying mechanism. We now investigated the effect of 2-IB treatment in P7 rat pups
Changlian Zhu et al.
Journal of neurochemistry, 90(2), 462-471 (2004-07-02)
Excessive nitric oxide (NO) production after cerebral hypoxia-ischaemia (HI) may induce cellular injury in various ways, including reaction with superoxide to form the highly reactive peroxynitrite. We characterized the spatial and temporal formation of peroxynitrite through immunohistochemical detection of nitrosylated
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