Cucurbit[8]uril is a highly efficient, low-toxic, orally bioactive supramolecular inducer of protein heterodimerization. Cucurbit[8]uril induces heterodimerization of methylviologen and naphthalene functionalized proteins. Cucurbit[8]uril induces energy transfer.

Physicochemical Properties

Molecular Formula	C48H48N32O16
Molecular Weight	1329.10
Exact Mass	1328.39
CAS #	259886-51-6
PubChem CID	16133299
Appearance	White to off-white solid powder
Density	2.71
LogP	-9.1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	0
Heavy Atom Count	96
Complexity	2960
Defined Atom Stereocenter Count	0
InChi Key	CONWISUOKHSUDR-UHFFFAOYSA-N
InChi Code	InChI=1S/C48H48N32O16/c81-33-49-1-50-18-20-54(34(50)82)4-58-22-24-62(38(58)86)8-66-26-28-70(42(66)90)12-74-30-32-78(46(74)94)15-77-31-29-73(45(77)93)11-69-27-25-65(41(69)89)7-61-23-21-57(37(61)85)3-53(33)19-17(49)51-2-52(18)36(84)56(20)6-60(22)40(88)64(24)10-68(26)44(92)72(28)14-76(30)48(96)80(32)16-79(31)47(95)75(29)13-71(27)43(91)67(25)9-63(23)39(87)59(21)5-55(19)35(51)83/h17-32H,1-16H2
Chemical Name	3,5,8,10,13,15,18,20,23,25,28,30,33,35,38,40,41,43,45,47,51,53,55,57,59,61,63,65,67,69,71,73-dotriacontazapentacosacyclo[35.3.3.36,7.311,12.316,17.321,22.326,27.331,32.22,41.236,43.13,40.15,8.110,13.115,18.120,23.125,28.130,33.135,38.145,51.147,73.153,55.157,59.161,63.165,67.169,71]octacontane-44,46,48,49,50,52,54,56,58,60,62,64,66,68,70,72-hexadecone
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.(2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Protein Heterodimerization[1]
ln Vitro	Cucurbit[8]uril (0~20 μM; 48 hours; CHO-K1 cells) causes a slight decrease in relative cell viability, to 86%[2]. Cucurbit[8]uril does, in fact, specifically cause the heterodimerization of MV–eYFP with Np–eCFP. The ternary complex can only form when all three supramolecular components are present because of the high energy transfer that Cucurbit[8]uril induces between the proteins. The methylviologen-induced unspecific protein assembly is inhibited in the presence of Cucurbit[8]uril. Selective protein heterodimers of more hydrophobic proteins can also be successfully formed using the Cucurbit[8]uril ternary system with methylviologen (MV) and naphthalene (NP). For the purpose of preventing MV-induced unspecific dimerization with hydrophobic protein surfaces, Cucurbit[8]uril as a host molecule must be present[1].
ln Vivo	Studies on mice administered orally also demonstrate the extremely low toxicity of cucurbit[8]uril when administered intravenously in vivo[2].
Cell Assay	Cell Viability Assay[1] Cell Types: CHO-K1 cells Tested Concentrations: 0~20 μM Incubation Duration: 48 hrs (hours) Experimental Results: At the highest investigated concentration of 20 μM after 48 h, the relative cell viability dropped marginally to 86%.
References	[1]. Cucurbit[8]uril induced heterodimerization of methylviologen and naphthalene functionalized proteins. Chem Commun (Camb). 2011;47(24):6798-6800. [2]. 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.
Additional Infomation	Cucurbit[8]uril is a cucurbituril.

Solubility Data

Solubility (In Vitro)

DMSO: < 1 mg/mL

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	0.7524 mL	3.7619 mL	7.5239 mL
	5 mM	0.1505 mL	0.7524 mL	1.5048 mL
	10 mM	0.0752 mL	0.3762 mL	0.7524 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.