Glu-urea-Glu-NHS ester (compound 21) is an active NHS Glu-urea-Glu that works as a pharmacophore for binding to prostate-specific membrane antigen (PSMA) inhibitors.

Physicochemical Properties

Molecular Formula	C27H43N3O11
Molecular Weight	585.643828630447
Exact Mass	585.289
CAS #	1228927-36-3
PubChem CID	59404242
Appearance	White to off-white solid powder
LogP	1.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	18
Heavy Atom Count	41
Complexity	1000
Defined Atom Stereocenter Count	2
SMILES	CC(C)(C)OC(=O)CC[C@@H](C(=O)OC(C)(C)C)NC(=O)N[C@@H](CCC(=O)ON1C(=O)CCC1=O)C(=O)OC(C)(C)C
InChi Key	RLHXPXLWGMDVAY-IRXDYDNUSA-N
InChi Code	InChI=1S/C27H43N3O11/c1-25(2,3)38-20(33)14-10-16(22(35)39-26(4,5)6)28-24(37)29-17(23(36)40-27(7,8)9)11-15-21(34)41-30-18(31)12-13-19(30)32/h16-17H,10-15H2,1-9H3,(H2,28,29,37)/t16-,17-/m0/s1
Chemical Name	ditert-butyl (2S)-2-[[(2S)-5-(2,5-dioxopyrrolidin-1-yl)oxy-1-[(2-methylpropan-2-yl)oxy]-1,5-dioxopentan-2-yl]carbamoylamino]pentanedioate
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]. Synthesis and SAR of ⁹⁹mTc/Re-labeled small molecule prostate specific membrane antigen inhibitors with novel polar chelates. Bioorg Med Chem Lett. 2013 Mar 1;23(5):1557-63.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~170.75 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (4.27 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 25.0 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	1.7075 mL	8.5377 mL	17.0753 mL
	5 mM	0.3415 mL	1.7075 mL	3.4151 mL
	10 mM	0.1708 mL	0.8538 mL	1.7075 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.