Cucurbit[8]uril 

Cucurbit[8]uril is a potent, low toxicity and orally active supramolecular inducer of protein heterodimerization. Cucurbit[8]uril induces heterodimerization of methylviologen and naphthalene functionalized proteins. Cucurbit[8]uril can induce energy transfer ^[1][2].

Protein Heterodimerization^[1]

Cucurbit[8]uril (0~20 μM; 48 hours; CHO-K1 cells) makes the relative cell viability dropped marginally to 86%^[2].
Cucurbit[8]uril indeed selectively induces the heterodimerization of MV–eYFP with Np–eCFP. Cucurbit[8]uril-induced high energy transfer between the proteins is only observed in the presence of all three supramolecular components, allowing the formation of the ternary complex. In the presence of Cucurbit[8]uril, the unspecific protein assembly induced by the methylviologen is inhibited. The ternary system of Cucurbit[8]uril with methylviologen (MV) and naphthalene (NP) can also be successfully used for the formation of selective protein heterodimers of more hydrophobic proteins. The presence of Cucurbit[8]uril as a host molecule is required to prevent MV induced unspecific dimerization with hydrophobic protein surfaces^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cucurbit[8]uril shows a very low toxicity of the in vivo intravenous injection, as well as oral administration studies on mice^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

1329.10

C₄₈H₄₈N₃₂O₁₆

259886-51-6

Solid

White to off-white

O=C1N(CN(C2=O)[C@]([C@@]3([H])N2CN(C4=O)[C@]([C@@]5([H])N4CN(C6=O)[C@]([C@@]7([H])N6CN8[C@]9([H])N(C%10=O)CN%117)([H])N(C%11=O)CN%125)([H])N(C%12=O)CN3C%13=O)([H])N%13CN%14%15)[C@]%14([H])[C@]%16([H])N1CN(C%17=O)[C@@]([C@]%18([H])N%17CN(C%19=O)[C@@]([C@]%20([H])N%19CN(C%21=O)[C@@]([C@]%22([H])N%21CN%23C8=O)([H])N(C(N%22CN%10[C@]%239[H])=O)CN%24%20)([H])N(C%24=O)CN%18C%25=O)([H])N%25CN%16C%15=O

Room temperature in continental US; may vary elsewhere.

4°C, protect from light, stored under nitrogen

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)

• [1]. Uhlenheuer DA, et al. Cucurbit[8]uril induced heterodimerization of methylviologen and naphthalene functionalized proteins. Chem Commun (Camb). 2011;47(24):6798-6800.  [Content Brief]

  [2]. Uzunova VD, et al. Toxicity of cucurbit[7]uril and cucurbit[8]uril: an exploratory in vitro and in vivo study. Org Biomol Chem. 2010;8(9):2037-2042.  [Content Brief]