DUPA(OtBu)-OH is a DUPA precursor. DUPA serves as a targeting motif for the delivery of Docetaxel (DTX) and may be utilized to study prostate tumors expressing prostate-specific membrane antigen (PSMA).

Physicochemical Properties

Molecular Formula	C23H40N2O9
Molecular Weight	488.571707725525
Exact Mass	488.273
CAS #	1026987-94-9
PubChem CID	87285592
Appearance	White to off-white solid powder
LogP	2.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	16
Heavy Atom Count	34
Complexity	743
Defined Atom Stereocenter Count	2
SMILES	O=C(OC(C)(C)C)CC[C@@H](C(OC(C)(C)C)=O)NC(N[C@H](C(OC(C)(C)C)=O)CCC(O)=O)=O
InChi Key	KBDDHSXZOLZZGF-GJZGRUSLSA-N
InChi Code	InChI=1S/C23H40N2O9/c1-21(2,3)32-17(28)13-11-15(19(30)34-23(7,8)9)25-20(31)24-14(10-12-16(26)27)18(29)33-22(4,5)6/h14-15H,10-13H2,1-9H3,(H,26,27)(H2,24,25,31)/t14-,15-/m0/s1
Chemical Name	(4S)-4-[[(2S)-1,5-bis[(2-methylpropan-2-yl)oxy]-1,5-dioxopentan-2-yl]carbamoylamino]-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid
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

ln Vitro	DUPA(OtBu)-OH (DUPA Precursor 17) is a 2-[3-(1,3-dicarboxypropyl)ureido]glutaric acid (DUPA) reagent [1]. The targeting ligand DUPA increases the transport capacity and selectivity of paclitaxel (PTX) to tumor cells via prostate-specific membrane antigen (PSMA)-mediated endocytosis. In addition, DUPA binds to PTX via disulfide bonds, which promotes quick and differentiated drug release in tumor cells [2].
ln Vivo	In treated mice, DUPA-targeted docetaxel (DTX) conjugates with longer spacers did not cause toxicity to the major organs [3].
References	[1]. DUPA conjugation of a cytotoxic indenoisoquinoline topoisomerase I inhibitor for selectiveprostate cancer cell targeting. J Med Chem. 2015 Apr 9;58(7):3094-103. [2]. Prostate-Specific Membrane Antigen Targeted Therapy of Prostate Cancer Using a DUPA-Paclitaxel Conjugate. Mol Pharm. 2018 May 7;15(5):1842-1852. [3]. Spacer length impacts the efficacy of targeted docetaxel conjugates in prostate-specificmembrane antigen expressing prostate cancer. J Drug Target. 2013 Dec;21(10):968-80.

Solubility Data

Solubility (In Vitro)

DMSO : ~125 mg/mL (~255.85 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (4.26 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 20.8 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: ≥ 2.08 mg/mL (4.26 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 20.8 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: ≥ 2.08 mg/mL (4.26 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 20.8 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	2.0468 mL	10.2339 mL	20.4679 mL
	5 mM	0.4094 mL	2.0468 mL	4.0936 mL
	10 mM	0.2047 mL	1.0234 mL	2.0468 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.