N-(2-Aminoethyl)biotinamide - CAS 111790-37-5

Biotin-EDA is a PROTAC linker, which is composed of alkyl chains. Biotin-EDA can be used to synthesize a range of PROTACs.

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Molecular Formula
C12H22N4O2S
Molecular Weight
286.39

N-(2-Aminoethyl)biotinamide

    • Specification
      • Purity
        95%
        Appearance
        Off-White to Pale Yellow Solid
        Storage
        2-8°C
        Shipping
        Room temperature in continental US; may vary elsewhere.
        IUPAC Name
        5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-(2-aminoethyl)pentanamide
        Synonyms
        (3aS,4S,6aR)-N-(2-Aminoethyl)hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide; [3aS-(3aα,4β,6aα)]-N-(2-Aminoethyl)hexahydro-2-oxo-
        1H-thieno[3,4-d]imidazole-4-pentanamide;
    • Properties
      • Boiling Point
        643.7°C at 760mmHg
        Melting Point
        172-174°C
        Density
        1.189g/cm3
        InChI Key
        BNCJEZWKLUBUBB-QXEWZRGKSA-N
        InChI
        InChI=1S/C12H22N4O2S/c13-5-6-14-10(17)4-2-1-3-9-11-8(7-19-9)15-12(18)16-11/h8-9,11H,1-7,13H2,(H,14,17)(H2,15,16,18)/t8-,9-,11-/m0/s1
        Canonical SMILES
        C1C2C(C(S1)CCCCC(=O)NCCN)NC(=O)N2
    • Reference Reading
      • 1. Multiple neuronal connexins in the mammalian retina
        Stephen C Massey, Jennifer J O'Brien, E Brady Trexler, Wei Li, Joyce W Keung, Stephen L Mills, John O'Brien Cell Commun Adhes. 2003 Jul-Dec;10(4-6):425-30.doi: 10.1080/cac.10.4-6.425.430.
        Gap junctions are abundant in the mammalian retina and many neuronal types form neural networks. Several different neuronal connexins have now been identified in the mammalian retina. Cx36 supports coupling in the AII amacrine cell network and is essential for processing rod signals. Cx36 is probably also responsible for photoreceptor coupling. Horizontal cells appear to be extensively coupled by either Cx50 or Cx57. These results indicate that multiple neuronal connexins are expressed in the mammalian retina and that different cell types express different connexins.
        2. A biotin-containing compound N-(2-aminoethyl)biotinamide for intracellular labeling and neuronal tracing studies: comparison with biocytin
        H Kita, W Armstrong Comparative StudyJ Neurosci Methods. 1991 Apr;37(2):141-50.doi: 10.1016/0165-0270(91)90124-i.
        The hydrochloride salt of a new, small molecular weight (M.W. = 286) biotin-containing compound referred to as biotinamide (N-(2-aminoethyl)biotinamide) was compared with biocytin (M.W. = 372) for its use in intracellular labeling of neurons and in neuronal tracing experiments using avidin conjugates for histochemical detection. The DC resistance and current passing ability of electrodes filled with 1-2 M potassium chloride, potassium acetate or potassium methylsulfate and containing 1-4% of these compounds were compared. Although differences were observed due to the electrolyte, with KCl electrodes being the least resistant, no electrode differences could be attributed to the concentration or type of tracer. However, whereas biocytin could be electrophoresed with either positive or negative current with roughly similar facility, biotinamide was selectively ejected with positive current. This would be beneficial to electrophysiologists using hyperpolarizing current to stabilize the membrane potential of neurons prior to recording. In addition, biotinamide-HCl could be dissolved at concentrations of 2-4% in either 1 or 2 M salt without precipitation, whereas biocytin precipitated in some of these solutions. Both compounds were equally useful for neuronal tracing experiments with survival times of 2 days, but labeling was much weaker with longer survival times. There was also little difference in the ability to histochemically localize these compounds using avidin conjugates, including avidin-biotin-horseradish peroxidase complex. In conclusion, biotinamide shares many of the useful features of biocytin, but can be selectively electrophoresed with positive current and can be dissolved at higher concentrations with little detriment in the electrical properties of the recording electrode.
        3. Spontaneous electrical activity in the prostate gland
        Betty Exintaris, Dan-Thanh T Nguyen, Anupa Dey, Richard J Lang Auton Neurosci. 2006 Jun 30;126-127:371-9.doi: 10.1016/j.autneu.2006.02.019.Epub 2006 Apr 19.
        The cellular mechanisms that underlie the initiation, maintenance and propagation of electrical activity in the prostate gland remain little understood. Intracellular microelectrode recordings have identified at least two distinct electrical waveforms: pacemaker potentials and slow wave activity. By analogy with the intestine, we have proposed that pacemaker activity arises from a morphologically distinct group of c-Kit positive interstitial cells that lie mainly between the glandular epithelium and smooth muscle layers. We speculate that pacemaker activity arising from the prostatic interstitial cells (PICs) is likely to propagate and initiate slow wave activity in the smooth muscle cells resulting in contraction of the stromal smooth muscle wall. While spontaneous electrical activity in the prostate gland is myogenic in origin, it is clear that nerve-mediated agents are able to modulate this activity. Excitatory agents such as histamine, phenylephrine and a raised potassium saline all increase slow wave discharge. In contrast, nitric oxide donors reduce or abolish the spontaneous electrical events. However, the cellular mechanisms underlying the action of various endogenously released agents remain to be elucidated.
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