(p-SCN-Bn)-NOTA - CAS 147597-66-8

(p-SCN-Bn)-NOTA - CAS 147597-66-8 Catalog number: BADC-01402

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(p-SCN-Bn)-NOTA is an ADC linker used in the synthesis of antibody-drug conjugates (ADCs).

Category
ADCs Linker
Product Name
(p-SCN-Bn)-NOTA
CAS
147597-66-8
Catalog Number
BADC-01402
Molecular Formula
C20H26N4O6S
Molecular Weight
450.51
(p-SCN-Bn)-NOTA

Ordering Information

Catalog Number Size Price Quantity
BADC-01402 100 mg $1364
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Description
(p-SCN-Bn)-NOTA is an ADC linker used in the synthesis of antibody-drug conjugates (ADCs).
Synonyms
NOTA-1; 1H-1,4,7-Triazonine-1,4,7-triacetic acid, hexahydro-2-[(4-isothiocyanatophenyl)methyl]-; p-SCN-Bn-NOTA; Hexahydro-2-[(4-isothiocyanatophenyl)methyl]-1H-1,4,7-triazonine-1,4,7-triacetic acid; 2-(4-Isothiocyanatobenzyl)-1,4,7-triazacyclonane-1,4,7-triacetic acid; 2-(p-isothiocyanatobenzyl)-1,4,7-triazacyclononane-1,4,7-triacetic acid
IUPAC Name
2-[4,7-bis(carboxymethyl)-5-[(4-isothiocyanatophenyl)methyl]-1,4,7-triazonan-1-yl]acetic acid
Canonical SMILES
C1CN(CC(N(CCN1CC(=O)O)CC(=O)O)CC2=CC=C(C=C2)N=C=S)CC(=O)O
InChI
InChI=1S/C20H26N4O6S/c25-18(26)11-22-5-6-23(12-19(27)28)10-17(24(8-7-22)13-20(29)30)9-15-1-3-16(4-2-15)21-14-31/h1-4,17H,5-13H2,(H,25,26)(H,27,28)(H,29,30)
InChIKey
ABEIJMWLNYUWMD-UHFFFAOYSA-N
Density
1.37±0.1 g/cm3
Solubility
Soluble in Aqueous Acid (Slightly), Water (Very Slightly)
Appearance
Off-white to Beige Solid
Purity
≥95%
Storage
Store at -20°C
Boiling Point
716.5±60.0°C at 760 mmHg

(p-SCN-Bn)-NOTA, a versatile bifunctional chelating agent crucial for radiolabeling in both imaging and therapeutic contexts, is exemplified through four key applications, presented with heightened perplexity and burstiness:

Radiopharmaceutical Development: Serving as a cornerstone in the chelation of radiometals like gallium-68 or copper-64 for positron emission tomography (PET) imaging, (p-SCN-Bn)-NOTA enables real-time, high-resolution visualization of intricate biological processes. Its exceptional stability and specificity position it as a favored choice for innovating cutting-edge radiopharmaceuticals, pushing the boundaries of diagnostic imaging.

Targeted Cancer Therapy: (p-SCN-Bn)-NOTA emerges as an indispensable asset in the realm of targeted cancer therapy, acting as the linchpin in attaching radiometals to monoclonal antibodies or peptides tailored to seek out cancer cells with precision. This strategic approach ensures the focused delivery of therapeutic radioisotopes directly to tumors, minimizing harm to healthy tissues. These advancements mark significant progress in enhancing the effectiveness and safety of radioimmunotherapy.

Biodistribution Studies: Researchers harness the power of (p-SCN-Bn)-NOTA to label biomolecules for biodistribution studies, tracking the intricate in vivo dispersion and accumulation of these entities across various organs and tissues. Understanding biodistribution is paramount in drug development, aiding in predicting pharmacokinetics and potential toxicities associated with therapeutic agents. The meticulous labeling with (p-SCN-Bn)-NOTA ensures the reliability and reproducibility of study outcomes, underpinning critical advancements in biomedical research.

Preclinical Research: (p-SCN-Bn)-NOTA finds utility in preclinical investigations, being utilized to label peptides, proteins, and small molecules for a diverse range of imaging applications. These studies offer invaluable insights into the binding, uptake, and clearance of labeled compounds in animal models. The versatility of (p-SCN-Bn)-NOTA empowers researchers to explore a wide array of biological phenomena, propelling the development of novel diagnostic and therapeutic strategies to new frontiers of discovery and innovation.

1.In vitro and in vivo evaluation of a 64Cu-labeled NOTA-Bn-SCN-Aoc-bombesin analogue in gastrin-releasing peptide receptor expressing prostate cancer
Nucl Med Biol. 2012 Jul;39(5):609-16. doi: 10.1016/j.nucmedbio.2011.12.004.
Introduction: Bombesin (BN) is an amphibian peptide that binds to the gastrin-releasing peptide receptor (GRPR). It has been demonstrated that BN analogues can be radiolabeled for potential diagnosis and treatment of GRPR-expressing malignancies. Previous studies have conjugated various chelators to the eight C-terminal amino acids of BN [BN(7-14)] for radiolabeling with 64Cu. Recently, (1,4,7-triazacyclononane-1,4,7-triacetic acid) (NOTA) has been evaluated as the five-coordinate 64Cu complex, with results indicating GRPR-specific tumor uptake. This study aimed to conjugate S-2-(4-isothiocyanatobenzyl)-NOTA (p-SCN-Bn-NOTA) to BN(7-14) such that it could form a six-coordinate complex with 64Cu and to evaluate the resulting peptide. Methods: p-SCN-NOTA was conjugated to 8-aminooctanoic acid (Aoc)-BN(7-14) in solution to yield NOTA-Bn-SCN-Aoc-BN(7-14). The unlabeled peptide was evaluated in a cell binding assay using PC-3 prostate cancer cells and 125I-Tyr4-BN to determine the IC50 value. The peptide was radiolabeled with 64Cu and evaluated for internalization into PC-3 cells and for tumor uptake in mice bearing PC-3 xenografts using biodistribution and micro-positron emission tomography imaging studies. Results: The binding assay demonstrated that NOTA-Bn-SCN-Aoc-BN(7-14) bound with high affinity to GRPR with an IC50 of 1.4 nM. The radiolabeled peptide demonstrated time-dependent internalization into PC-3 cells. In vivo, the peptide demonstrated tumor-specific uptake and imaging that were comparable to those of previously reported 64Cu-labeled BN analogues. Conclusions: These studies demonstrate that 64Cu-NOTA-Bn-SCN-Aoc-BN(7-14) binds to GRPR-expressing cells and that it can be used for imaging of GRPR-expressing prostate cancer.
2.Stability analysis of glutamic acid linked peptides coupled to NOTA through different chemical linkages
Mol Pharm. 2014 Nov 3;11(11):3867-74. doi: 10.1021/mp400706q.
Glutamic acid is a commonly used linker to form dimeric peptides with enhanced binding affinity than their corresponding monomeric counterparts. We have previously labeled NOTA-Bn-NCS-PEG3-E[c(RGDyK)]2 (NOTA-PRGD2) [1] with [(18)F]AlF and (68)Ga for imaging tumor angiogenesis. The p-SCN-Bn-NOTA was attached to E[c(RGDyK)]2 [2] through a mini-PEG with a thiourea linkage, and the product [1] was stable at radiolabeling condition of 100 °C and pH 4.0 acetate buffer. However, when the same p-SCN-Bn-NOTA was directly attached to the α-amine of E[c(RGDfK)]2 [3], the product NOTA-Bn-NCS-E[c(RGDfK)]2 [4] became unstable under similar conditions and the release of monomeric c(RGDfK) [5] was observed. The purpose of this work was to use HPLC and LC-MS to monitor the decomposition of glutamic acid linked dimeric peptides and their NOTA derivatives. A c(RGDyK) [6] and bombesin (BBN) [7] heterodimer c(RGDyK)-E-BBN [8], and a dimeric bombesin E(BBN)2 [9], both with a glutamic acid as the linker, along with a model compound PhSCN-E[c(RGDfK)] [10] were also studied. All the compounds were dissolved in 0.5 M pH 4.0 acetate buffer at the concentration of 1 mg/mL, and 0.1 mL of each sample was heated at 100 °C for 10 min and the more stable compounds were heated for another 30 min. The samples at both time points were analyzed with analytical HPLC to monitor the decomposition of the heated samples. The samples with decomposition were further analyzed by LC-MS to determine the mass of products from the decomposition for possible structure elucidation. After 10 min heating, the obvious release of c(RGDfK) [5] was observed for NOTA-Bn-NCS-E[c(RGDfK)]2 [4] and Ph-SCN-E[c(RGDfK)] [10]. Little or no release of monomers was observed for the remaining samples at this time point. After further heating, the release of monomers was clearly observed for E[c(RGDyK)]2 [2], E[c(RGDfK)]2 [3], c(RGDyK)-E-BBN [8], and E(BBN)2 [9]. No decomposition or little decomposition was observed for NOTA-Bn-NCS-PEG3-E[c(RGDyK)]2 [1], PEG3-E[c(RGDyK)]2 [11], NOTA-E[c(RGDyK)]2 [12], and NOTA-PEG3-E[c(RGDyK)]2 [13]. The glutamic acid linked dimeric peptides with a free α-amine are labile due to the neighboring amine participation in the hydrolysis. The stability of peptides could be increased by converting the free amine into amide. The instability of thiourea derivatives formed from α-amine was caused by participation of thiol group derived from thiourea.
3.64Cu-Labeled Aptamers for Tumor-Targeted Radionuclide Delivery
Methods Mol Biol. 2019;1974:223-231. doi: 10.1007/978-1-4939-9220-1_17.
Aptamers are a class of oligonucleotides with high binding affinity and specificity with their targets. Additionally, aptamers are nontoxic, very thermally stable, and able to reversibly undergo denaturation and have a small size. Cancer-related aptamers can be used for tumor-targeted drug delivery, such as to deliver diagnostic and therapeutic radionuclides to target cancers. We describe the process for preparing a 64 Cu-labeled modified A10 aptamer to target prostate cancer by conjugating and radiolabeling. The modified A10 aptamer was conjugated with p-SCN-Bn-NOTA as the chelator. Following this, the aptamer can be radiolabeled with the 64 Cu radioisotope. NOTA was selected as the chelator of choice due to its commercial availability and widely demonstrated in vivo stability with the 64 Cu radioisotope. Using this system, prostate cancer could potentially be targeted for noninvasive imaging using positron emission tomography (PET). Closely following this protocol allows many aptamers to be successfully radiolabeled to accurately and quantitatively trace their distribution in vivo for a wide range of medical applications.
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Historical Records: (p-SCN-Bn)-NOTA
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