1025796-31-9

Basic information

• Product Name: (S)-Di-Tert-Butyl 2-(3-((S)-6-Amino-1-(Tert-Butoxy)-1-Oxohexan-2-Yl)Ureido)Pentanedioate
• Synonyms: (S)-Di-Tert-Butyl 2-(3-((S)-6-Amino-1-(Tert-Butoxy)-1-Oxohexan-2-Yl)Ureido)Pentanedioate;(S)-Di-Tert-Butyl 2-(3-((S)-6-Amino-1-(Tert-Butoxy)-1-Oxohexan-2-Yl)Ureido)Pentanedioate(WXC02272)
• CAS NO: 1025796-31-9
• Molecular Formula: C₂₄H₄₅N₃O₇
• Molecular Weight: 487.63
• Mol File: 1025796-31-9.mol

Chemical Properties

• Boiling Point: 596.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.072±0.06 g/cm3(Predicted)
• PKA: 12.09±0.46(Predicted)
• CAS DataBase Reference: (S)-Di-Tert-Butyl 2-(3-((S)-6-Amino-1-(Tert-Butoxy)-1-Oxohexan-2-Yl)Ureido)Pentanedioate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Di-Tert-Butyl 2-(3-((S)-6-Amino-1-(Tert-Butoxy)-1-Oxohexan-2-Yl)Ureido)Pentanedioate(1025796-31-9)
• EPA Substance Registry System: (S)-Di-Tert-Butyl 2-(3-((S)-6-Amino-1-(Tert-Butoxy)-1-Oxohexan-2-Yl)Ureido)Pentanedioate(1025796-31-9)

Safety Data

• Hazardous Substances Data: 1025796-31-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-Di-Tert-Butyl 2-(3-((S)-6-Amino-1-(Tert-Butoxy)-1-Oxohexan-2-Yl)Ureido)Pentanedioate is used as a reactant in the synthesis of novel multivalent fluorescent inhibitors. These inhibitors demonstrate high affinity to prostate cancer cells, making them potentially valuable in the development of targeted therapies for the treatment of prostate cancer.
In the field of medicinal chemistry, (S)-Di-Tert-Butyl 2-(3-((S)-6-Amino-1-(Tert-Butoxy)-1-Oxohexan-2-Yl)Ureido)Pentanedioate serves as a key building block for the creation of new drugs with improved specificity and efficacy against cancer. Its unique structure allows for the formation of multivalent inhibitors that can bind to multiple sites on a target protein, increasing the potency and selectivity of the drug.
Additionally, the compound's fluorescent properties enable real-time monitoring of the drug's interaction with its target, providing valuable information on the drug's mechanism of action and potential optimization strategies.

Upstream product

• 1025796-30-8 (S)-2-[3-((S)-(5-benzyloxycarbonylamino)-1-tert-butoxycarbonylpentyl)ureido]pentanedioic acid di-tert-butyl ester 
• 32677-01-3 L-glutamic acid di-tert-butyl ester hydrochloride 
• 63628-63-7 Nε-benzyloxycarbonyl-L-lysine tert-butyl ester 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 5978-22-3 N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride 
• 1426213-63-9 N(ε)-benzoyloxycarbonyl-L-lysine-tert-butyl ester hydrochloride 
• 16874-06-9 di-tert-butyl L-glutamate 
• 180839-17-2 di-tert-butyl (S)-2-isocyanatopentanedioate 
• 1025796-29-5 (S)-2-[(imidazole-1-carbonyl)amino]pentanedioic acid di-tert-butyl ester 
• 14529-23-8 (S)-2-Amino-6-tert-butoxycarbonylamino-hexanoic acid tert-butyl ester 
• 156079-00-4 di-tert-butyl <<(4-nitrophenyl)oxy>carbonyl>-L-glutamate 

Downstream Products

• 949575-21-7 (S)-di-tert-butyl 2-(3-((S)-1-tert-butoxy-1-oxo-6-(4-(trimethylstannyl)benzylamino)hexan-2-yl)ureido)pentanedioate 
• 1196732-45-2 (S)-2-(3-((S)-1-carboxy-5-(4-(25-(2,4-dinitrophenylamino)-2,5,8,11,14,17,20,23-octaoxapentacosyl)-1H-1,2,3-triazol-1-yl)pentyl)ureido)pentanedioic acid 
• 1610413-98-3 C₃₁H₄₈N₄O₁₁ 
• 1610413-97-2 C₃₄H₅₄N₄O₁₀ 
• 1610414-00-0 C₃₃H₄₅N₇O₁₇S 

Relevant articles and documents

A Bivalent Inhibitor of Prostate Specific Membrane Antigen Radiolabeled with Copper-64 with High Tumor Uptake and Retention

Molecules containing lysine-ureido-glutamate functional groups bind to the active site of prostate specific membrane antigen, which is overexpressed in prostate cancer. To prepare copper radiopharmaceuticals for the diagnosis and therapy of prostate cancer, macrobicyclic sarcophagine ligands tethered to either one or two lysine-ureido-glutamate functional groups through an appropriate linker have been prepared. Sarcophagine ligands can be readily radiolabeled with positron-emitting copper-64 at room temperature. The bivalent agent, in which two targeting groups are tethered to a single copper complex, dramatically outperforms the monomeric agent with respect to tumor uptake and retention. The high tumor uptake, low background, and prolonged tumor retention, even at 24 hours post injection, suggest the bivalent agent is a promising diagnostic for prostate cancer and could be used for prospective dosimetry for therapy with a copper-67 variant.

Two is better than one: Difunctional high-affinity PSMA probes based on a [CpM(CO)3] (M = Re/99mTc) scaffold

More than 10% of all men will be given the diagnosis "prostate cancer" during their lifetime. Most of the current radio-diagnostic vehicles involve both expensive and localized production with cyclotrons as well as the use of bulky chelators for the radiometal. We report the use of a new multifunctional cyclopentadiene (Cp) platform to prepare difunctional and monofunctional, PSMA-targeting rhenium and technetium-99m complexes. The Cp-complexes and the free ligands are prepared by straightforward functionalization with either one or two Lys-urea-Glu (LuG) PSMA binding motifs. Cell binding assays revealed that the difunctional rhenium complex displays a dissociation constant (KD = 2.1 nM) that is an order of magnitude lower than the monofunctional compound (KD = 24.2 nM). The 99mTc complexes can be prepared in one step and ≤15 min in high yields. These difunctional Cp-Re(i)/99mTc(i) complexes represent a new class of imaging agents with binding affinities comparable to clinically evaluated compounds. Additionally, this study demonstrates that the Cp-platform can readily be derivatized with amine-containing biomolecules. Extending this work to incorporate both targeting and therapeutic moieties could lead to theranostic systems with Re/99mTc.

Chemically synthesized molecules with the targeting and effector functions of antibodies

This article reports the design, synthesis, and evaluation of a novel class of molecules of intermediate size (approximately 7000 Da), which possess both the targeting and effector functions of antibodies. These compounds-called synthetic antibody mimics targeting prostate cancer (SyAM-Ps)-bind simultaneously to prostate-specific membrane antigen and Fc gamma receptor I, thus eliciting highly selective cancer cell phagocytosis. SyAMs have the potential to combine the advantages of both small-molecule and biologic therapies, and may address many drawbacks associated with available treatments for cancer and other diseases.

Design and synthesis of a novel BODIPY-labeled PSMA inhibitor

Prostate-specific membrane antigen (PSMA) is a zinc-bound metalloprotease which is highly expressed in metastatic prostate cancer. It has been considered an excellent target protein for prostate cancer imaging and targeted therapy because it is a membrane protein and its active site is located in the extracellular region. We successfully synthesized and evaluated a novel PSMA ligand conjugated with BODIPY650/665. Compound 1 showed strong PSMA-inhibitory activity and selective uptake into PSMA-expressing tumors. Compound 1 has the potential to be utilized as a near infrared (NIR) optical imaging probe targeting PSMA-expressing cancers.

Synthesis and automated fluorine-18 radiolabeling of new PSMA-617 derivatives with a CuAAC radiosynthetic approach

In the last decade, the development of new radiopharmaceuticals for the imaging and therapy of prostate cancer has been a highly active and important area of research, especially focusing on the prostate-specific membrane antigen (PSMA), an antigen which

Prostate-specific membrane antigen (PSMA) targeted singlet oxygen delivery via endoperoxide tethered ligands

Singlet oxygen is the primary agent responsible for the therapeutic effects of photodynamic therapy (PDT). In this work, we demonstrate that singlet oxygen release due to thermal endoperoxide cycloreversion can be targeted towards specific features of sel

PSMA TARGETING UREA-BASED LIGANDS FOR PROSTATE CANCER RADIOTHERAPY AND IMAGING

The present invention provides novel PSMA targeting urea-based ligands that bind to prostate-specific membrane antigen (PSMA) which is expressed 8-to-12-fold higher in prostate cancer cells when compared to healthy tissue. The PSMA targeting urea-based li

COVALENT IMMUNE RECRUITER COMPOUNDS FOR IMMUNE CELL RECOGNITION AND ASSOCIATED USES

The present application relates to compounds of Formula I comprising an antibody binding domain (ABD) comprising a hapten that binds to an antibody in a subject, the antibody comprising a hapten binding site, an antibody labelling domain (ALD) comprising a functional group that forms a covalent bond with an amino acid in the antibody that is proximal to the hapten binding site and the formation of the covalent bond results in elimination of the ABD and either a target binding domain (TBD) or a detection moiety domain (DMD), each domain being optionally connected with independently selected linkers. The present application also includes methods and uses of the compounds, for example, for immune recognition of target cells by recruited labelled antibodies. [in-line-formulae]ABD?(L1)n-ALD-(L2)m-R[/in-line-formulae]

CONJUGATE OF FLUORESCENT DYE FOR THE VISUALIZATION OF PSMA EXPRESSING CELLS

The invention relates to the field of organic and medicinal chemistry, as well as molecular biology, and concerns a new class of compounds for imaging PSMA expressing cells and tissues, such as prostate cancer cells. New diagnostic conjugates for the visu

Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them

Prostate-specific membrane antigen (PSMA), also known as glutamate carboxypeptidase II (GCPII), is a suitable target for specific delivery of antitumor drugs and diagnostic agents due to its overexpression in prostate cancer cells. In the current work, we describe the design, synthesis, and biological evaluation of novel low-molecular PSMA ligands and conjugates with fluorescent dyes FAM-5, SulfoCy5, and SulfoCy7. In vitro evaluation of synthesized PSMA ligands on the activity of PSMA shows that the addition of aromatic amino acids into a linker structure leads to a significant increase in inhibition. The conjugates of the most potent ligand with FAM-5 as well as SulfoCy5 demonstrated high affinities to PSMA-expressing tumor cells in vitro. In vivo biodistribution in 22Rv1 xenografts in Balb/c nude mice of PSMA-SulfoCy5 and PSMA-SulfoCy7 conjugates with a novel PSMA ligand demonstrated good visualization of PSMA-expressing tumors. Also, the conjugate PSMA-SulfoCy7 demonstrated the absence of any explicit toxicity up to 87.9 mg/kg.