1025796-30-8

Basic information

• Product Name: (S)-2-[3-((S)-(5-benzyloxycarbonylamino)-1-tert-butoxycarbonylpentyl)ureido]pentanedioic acid di-tert-butyl ester
• Synonyms: (S)-2-[3-((S)-(5-benzyloxycarbonylamino)-1-tert-butoxycarbonylpentyl)ureido]pentanedioic acid di-tert-butyl ester
• CAS NO: 1025796-30-8
• Molecular Weight: 621.772
• Mol File: 1025796-30-8.mol
• Article Data: 45

Chemical Properties

• CAS DataBase Reference: (S)-2-[3-((S)-(5-benzyloxycarbonylamino)-1-tert-butoxycarbonylpentyl)ureido]pentanedioic acid di-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-[3-((S)-(5-benzyloxycarbonylamino)-1-tert-butoxycarbonylpentyl)ureido]pentanedioic acid di-tert-butyl ester(1025796-30-8)
• EPA Substance Registry System: (S)-2-[3-((S)-(5-benzyloxycarbonylamino)-1-tert-butoxycarbonylpentyl)ureido]pentanedioic acid di-tert-butyl ester(1025796-30-8)

Safety Data

• Hazardous Substances Data: 1025796-30-8(Hazardous Substances Data)

Usage

Description

(S)-2-[3-((S)-(5-benzyloxycarbonylamino)-1-tert-butoxycarbonylpentyl)ureido]pentanedioic acid di-tert-butyl ester is a complex organic compound characterized by its unique molecular structure. It is a derivative of pentanedioic acid with di-tert-butyl ester groups and a ureido functional group. The compound features a chiral center, denoted by the (S)-configuration, and contains a benzyloxycarbonyl group and a tert-butoxycarbonyl group, which are commonly used as protecting groups in organic synthesis. This molecule has potential applications in various fields due to its structural features and functional groups.

Uses

Used in Pharmaceutical Industry:
(S)-2-[3-((S)-(5-benzyloxycarbonylamino)-1-tert-butoxycarbonylpentyl)ureido]pentanedioic acid di-tert-butyl ester is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block for the development of new drugs, particularly those targeting specific biological receptors or enzymes.
Used in Chemical Research:
In the field of chemical research, (S)-2-[3-((S)-(5-benzyloxycarbonylamino)-1-tert-butoxycarbonylpentyl)ureido]pentanedioic acid di-tert-butyl ester serves as a key compound for studying the reactivity and selectivity of various chemical reactions. Its structural features allow researchers to explore new synthetic routes and develop innovative methodologies for the preparation of complex organic molecules.
Used in Synthesis of Labelling and Tracer Molecules:
(S)-2-[3-((S)-(5-benzyloxycarbonylamino)-1-tert-butoxycarbonylpentyl)ureido]pentanedioic acid di-tert-butyl ester is used as a precursor in the synthesis of labelling and tracer molecules. These molecules are essential tools in various scientific disciplines, including biochemistry, molecular biology, and medical imaging, where they help in the detection, localization, and quantification of specific biological processes or molecules.

Upstream product

• 32677-01-3 L-glutamic acid di-tert-butyl ester hydrochloride 
• 63628-63-7 Nε-benzyloxycarbonyl-L-lysine tert-butyl ester 
• 5978-22-3 N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 16874-06-9 di-tert-butyl L-glutamate 
• 1426213-63-9 N(ε)-benzoyloxycarbonyl-L-lysine-tert-butyl ester hydrochloride 
• 180839-17-2 di-tert-butyl (S)-2-isocyanatopentanedioate 
• 1025796-29-5 (S)-2-[(imidazole-1-carbonyl)amino]pentanedioic acid di-tert-butyl ester 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 156079-00-4 di-tert-butyl <<(4-nitrophenyl)oxy>carbonyl>-L-glutamate 
• 1105575-31-2 CF₃O₃S^(1-)*C₁₈H₃₀N₃O₅⁽¹⁺⁾ 

Downstream Products

• 1025796-31-9 (S)-2-[3-((S)-5-amino-1-tert-butoxycarbonylpentyl)ureido]pentanedioic acid di-tert-butyl ester 
• 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 
• 1610413-97-2 C₃₄H₅₄N₄O₁₀ 
• 1610413-98-3 C₃₁H₄₈N₄O₁₁ 
• 1610414-00-0 C₃₃H₄₅N₇O₁₇S 

Relevant articles and documents

Enzymatic radiosynthesis of a18F-Glu-Ureido-Lys ligand for the prostate-specific membrane antigen (PSMA)

Prostate cancer represents a major public health threat as it is one of the most common male cancers worldwide. The prostate-specific membrane antigen (PSMA) is highly over-expressed in prostatic cancer cells in a manner that correlates with both tumour s

Synthesis and biological evaluation of Doxorubicin-containing conjugate targeting PSMA

Prostate-specific membrane antigen (PSMA), also known as glutamate carboxypeptidase II (GCPII), has recently emerged as a prominent biomarker of prostate cancer (PC) and as an attractive protein trap for drug targeting. At the present time, several drugs and molecular diagnostic tools conjugated with selective PSMA ligands are actively evaluated in different preclinical and clinical trials. In the current work, we discuss design, synthesis and a preliminary biological evaluation of PSMA-specific small-molecule carrier equipped by Doxorubicin (Dox). We have introduced an unstable azo-linker between Dox and the carrier hence the designed compound does release the active substance inside cancer cells thereby providing a relatively high Dox concentration in nuclei and a relevant cytotoxic effect. In contrast, we have also synthesized a similar conjugate with a stable amide linker and it did not release the drug at all. This compound was predominantly accumulated in cytoplasm and did not cause cell death. Preliminary in vivo evaluation has showed good efficiency for the degradable conjugate against PC3-PIP(PSMA+)-containing xenograft mine. Thus, we have demonstrated that the conjugate can be used as a template to design novel analogues with improved targeting, anticancer activity and lower rate of potential side effects. 3D molecular docking study has also been performed to elucidate the underlying mechanism of binding and to further optimization of the linker area for improving the target affinity.

Synthesis of a porphyrin with histidine-like chelate: an efficient path towards molecular PDT/SPECT theranostics

The goal of “personalised” medicine has seen a growing interest in the development of theranostic agents. Bifunctional, and targeted-trifunctional, theranostic water-soluble porphyrins with a histidine-like chelating group have been synthesisedviacopper-catalysed azide-alkyne cycloaddition (CuAAC) “click” chemistry in high yield and purity. They are capable of photodynamic treatment and [99mTc(CO)3]+complexation for single-photon emission computed tomography (SPECT) imaging, with a radiochemical yield of >95%. The toxicity and phototoxicity were evaluated on HT-29 cells, DU145, and DU145-PSMA cell lines, with the targeted theranostic showing more potent phototoxicity towards DU145-PSMA expressing cells.

Development of a Ga-68 labeled PET tracer with short linker for prostate-specific membrane antigen (PSMA) targeting

Glu-Urea-Lys (GUL) derivatives have been reported as prostate-specific membrane antigen (PSMA) agent. We developed derivatives of GUL conjugated with NOTA or DOTA via a thiourea linker and tested their feasibility as PSMA imaging agents after labeling wit

Preparation and biological evaluation of [99m Tc]Tc-CNGU as a PSMA-targeted radiotracer for the imaging of prostate cancer

Prostate-specific membrane antigen (PSMA) is a well-established biological target that is overexpressed on the surface of prostate cancer lesions. Radionuclide-labeled small-molecule PSMA inhibitors have been shown to be promising PSMA-specific agents for the diagnosis and therapy of prostate cancer. In this study, a glutamate-urea-based PSMA-targeted ligand containing an isonitrile (CNGU) was synthesized and labeled with99m Tc to prepare [99m Tc]Tc-CNGU with a high radiochemical purity (RCP). The CNGU ligand showed a high affinity toward PSMA (Ki value is 8.79 nM) in LNCaP cells. The [99m Tc]Tc-CNGU exhibited a good stability in vitro and hydrophilicity (log P = ?1.97 ± 0.03). In biodistribution studies, BALB/c nude mice bearing LNCaP xenografts showed that the complex had a high tumor uptake with 4.86 ± 1.19% ID/g, which decreased to 1.74 ± 0.90% ID/g after a pre-injection of the selective PSMA inhibitor ZJ-43, suggesting that it was a PSMA-specific agent. Micro-SPECT imaging demonstrated that the [99m Tc]Tc-CNGU had a tumor uptake and that the uptake was reduced in the image after blocking with ZJ-43, further confirming its PSMA specificity. All of the results in this work indicated that [99m Tc]Tc-CNGU is a promising PSMA-specific tracer for the imaging of prostate cancer.

Polypeptide-based molecular platform and its docetaxel/sulfo-cy5-containing conjugate for targeted delivery to prostate specific membrane antigen

A strategy for stereoselective synthesis of molecular platform for targeted delivery of bimodal therapeutic or theranostic agents to the prostate-specific membrane antigen (PSMA) receptor was developed. The proposed platform contains a urea-based, PSMA-targeting Glu-Urea-Lys (EuK) fragment as a vector moiety and tripeptide linker with terminal amide and azide groups for subsequent addition of two different therapeutic and diagnostic agents. The optimal method for this molecular platform synthesis includes (a) solid-phase assembly of the polypeptide linker, (b) coupling of this linker with the vector fragment, (c) attachment of 3-aminopropylazide, and (d) amide and carboxylic groups deprotection. A bimodal theranostic conjugate of the proposed platform with a cytostatic drug (docetaxel) and a fluorescent label (Sulfo-Cy5) was synthesized to demonstrate its possible sequential conjugation with different functional molecules.

Hybrid chelator-based PSMA radiopharmaceuticals: Translational approach

(1) Background: Prostate-specific membrane antigen (PSMA) has been extensively studied in the last decade. It became a promising biological target in the diagnosis and therapy of PSMAexpressing cancer diseases. Although there are several radiolabeled PSMA

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.