Thalidomide-propargyl is a Thalidomide-based Cereblon ligand that recruits CRBN protein. Thalidomide-propargyl can be connected to the target protein ligand through a linker to form an IMiD-containing PROTAC. Thalidomide-propargyl is a reagent for click chemistry. It has Alkyne groups and could undergo CuAAc (copper-catalyzed azide-alkyne cycloaddition reaction) with compounds bearing Azide groups.

Physicochemical Properties

Molecular Formula	C16H12N2O5
Molecular Weight	312.2769
Exact Mass	312.074
CAS #	2098487-39-7
PubChem CID	132118478
Appearance	White to off-white solid powder
LogP	0.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Heavy Atom Count	23
Complexity	619
Defined Atom Stereocenter Count	0
SMILES	O=C1C([H])(C([H])([H])C([H])([H])C(N1[H])=O)N1C(C2C([H])=C([H])C([H])=C(C=2C1=O)OC([H])([H])C#C[H])=O
InChi Key	NOGQTNDSZFYNTM-UHFFFAOYSA-N
InChi Code	InChI=1S/C16H12N2O5/c1-2-8-23-11-5-3-4-9-13(11)16(22)18(15(9)21)10-6-7-12(19)17-14(10)20/h1,3-5,10H,6-8H2,(H,17,19,20)
Chemical Name	2-(2,6-dioxopiperidin-3-yl)-4-prop-2-ynoxyisoindole-1,3-dione
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
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

References

[1]. A "Click Chemistry Platform" for the Rapid Synthesis of Bispecific Molecules for Inducing Protein Degradation. J Med Chem. 2018 Jan 25;61(2):453-461.

Solubility Data

Solubility (In Vitro)

DMSO : ~16.67 mg/mL (~53.38 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 1.67 mg/mL (5.35 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.67 mg/mL (5.35 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 1.67 mg/mL (5.35 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.2023 mL	16.0113 mL	32.0225 mL
	5 mM	0.6405 mL	3.2023 mL	6.4045 mL
	10 mM	0.3202 mL	1.6011 mL	3.2023 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.