Merck
CN
All Photos(2)

Documents

I4632

Sigma-Aldrich

2-Iminobiotin

≥98% (TLC)

Sign Into View Organizational & Contract Pricing
All Photos(2)
Synonym(s):
Guanidinobiotin, Hexahydro-2-imino-1H-thieno[3,4-d]imidazole-4-pentanoic acid
Empirical Formula (Hill Notation):
C10H17N3O2S
CAS Number:
13395-35-2
Molecular Weight:
243.33
Beilstein:
18952
MDL number:
MFCD00066150
PubChem Substance ID:
24896060
NACRES:
NA.46

biological source

synthetic (organic)

Quality Level

200

Assay

≥98% (TLC)

form

powder

solubility

1 M HCl: 50 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=N)N2

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

InChI key

WWVANQJRLPIHNS-ZKWXMUAHSA-N

Looking for similar products? Visit Product Comparison Guide

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.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

S Tracey Bjorkman et al.
Stroke, 44(3), 809-811 (2013-01-31)
To determine the optimal dose of 2-iminobiotin (2-IB) for the treatment of moderate to severe asphyxia in a neonatal piglet model of hypoxia-ischemia. Newborn piglets were subjected to a 30-minute hypoxia-ischemia insult and randomly treated with vehicle or 2-IB (0.1
Cacha Peeters-Scholte et al.
Experimental brain research, 156(1), 20-26 (2003-12-23)
Early detection of delayed cerebral energy failure may be important in the prevention of reperfusion injury of the brain after severe perinatal hypoxia-ischaemia (HI). This study investigated whether monitoring of the redox state of cytochrome aa(3) (Cytaa(3)) with near infrared
F K Athappilly et al.
Protein science : a publication of the Protein Society, 6(6), 1338-1342 (1997-06-01)
Streptavidin binds 2'-iminobiotin in a pH-dependent fashion--affinity decreases as the pH is lowered. This property makes the purification of compounds conjugated to streptavidin or immobiotin possible under mild conditions by affinity chromatography. In order to understand the molecular details of
Hiroyuki Inoue et al.
Biomacromolecules, 6(1), 27-29 (2005-01-11)
A layer-by-layer thin film composed of avidin and 2-iminobiotin-labeled poly(ethyleneimine) (ib-PEI) was prepared and their sensitivity to the environmental pH and biotin was studied. The avidin/ib-PEI multilayer assemblies were stable at pH 8-12, whereas the assemblies were decomposed at pH
Tijen Utkan et al.
Pharmacology, biochemistry, and behavior, 101(4), 515-519 (2012-03-13)
The aim of this study was to compare the effects of both neuronal NOS (nNOS) and inducible NOS (iNOS) inhibitor 2-iminobiotin, with the more selective nNOS inhibitor N(ω)-propyl-L-arginine (NPLA) and selective inducible NOS (iNOS) inhibitor aminoguanidine, on emotional learning, working
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service