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N3-L-Cit-OH DCHA

  CAS No.: 2737202-65-0   Cat No.: BADC-01783   Purity: >98% 4.5  

N3-Cit DCHA is an azide-functionalized citrulline-based cleavable linker intermediate for antibody-drug conjugates, facilitating selective intracellular payload release. Keywords: ADC linker, citrulline linker, cleavable linker, azide linker.

N3-L-Cit-OH DCHA

Structure of 2737202-65-0

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ADC Linker
Molecular Formula
C18H34N6O3
Molecular Weight
382.50
Storage
Store at 2-8 °C

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Synonyms
N3-L-Cit-OH dicyclohexylamine salt; N3-Cit-OH DCHA; N-Cyclohexylcyclohexanaminium (2S)-2-azido-5-(carbamoylamino)pentanoate; N3-Cit.DCHA; (S)-2-Azido-citrulline dicyclohexylamine; Azido-citrulline dicyclohexylammonium salt
IUPAC Name
(2S)-2-azido-5-(carbamoylamino)pentanoic acid;N-cyclohexylcyclohexanamine
Canonical SMILES
C1CCC(CC1)NC2CCCCC2.C(C[C@@H](C(=O)O)N=[N+]=[N-])CNC(=O)N
InChI
InChI=1S/C12H23N.C6H11N5O3/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;7-6(14)9-3-1-2-4(5(12)13)10-11-8/h11-13H,1-10H2;4H,1-3H2,(H,12,13)(H3,7,9,14)/t;4-/m.0/s1
InChIKey
PRCFSZNWPCQNEC-VWMHFEHESA-N
Storage
Store at 2-8 °C

N3-Cit DCHA is a specialized chemical compound that combines a citrulline (Cit) moiety with a DCHA (D-α-(N-Carboxymethyl)histamine) group. This structure allows N3-Cit DCHA to serve as a versatile building block in various biomedical and pharmaceutical applications. Its unique chemical properties, including the presence of a carboxymethyl group and an amino acid-based structure, make it valuable for targeted drug delivery, peptide synthesis, and enzyme modulation. The ability to modify the citrulline residue adds flexibility to its use in therapeutic and research applications.

One of the key applications of N3-Cit DCHA is in the development of peptide-based drug delivery systems. The citrulline moiety can serve as a targeting ligand for specific receptors overexpressed in certain diseases, such as cancer. When conjugated to therapeutic agents, N3-Cit DCHA can selectively guide these agents to diseased tissues, improving the efficacy of the treatment while reducing off-target effects. Additionally, the DCHA group may be used to improve the solubility and stability of the conjugated molecules, enabling more efficient drug delivery and better pharmacokinetics. This makes N3-Cit DCHA an attractive candidate in targeted cancer therapies, particularly for chemotherapeutic agents that require precise delivery.

N3-Cit DCHA is also useful in the design of prodrugs, where it serves as a precursor or intermediate to more potent compounds. The DCHA group can undergo hydrolysis or other metabolic processes, releasing the active drug at the target site. This approach enhances the specificity of the drug while minimizing systemic exposure, which can help reduce side effects. In particular, the citrulline-derived moiety may allow for selective activation in tissues with specific enzymatic profiles, such as tumor tissues, making N3-Cit DCHA an ideal component in the creation of prodrug systems for oncology or inflammatory diseases.

Another application of N3-Cit DCHA is in enzyme-targeted therapies, where the compound can be used to modulate the activity of specific enzymes involved in disease progression. The carboxymethyl histamine group within N3-Cit DCHA allows it to interact with enzymes or receptors that are sensitive to histamine or its derivatives. By binding to these targets, N3-Cit DCHA may either inhibit or stimulate enzyme activity, depending on the context, providing a tool for developing enzyme modulators. This is particularly useful in the treatment of diseases such as rheumatoid arthritis, where enzymes like histamine-degrading enzymes play a critical role.

Furthermore, N3-Cit DCHA can play a significant role in the field of molecular imaging and diagnostics. Its chemical structure allows for the easy attachment of imaging agents, such as fluorescent dyes or radiolabels, which can be used to track the compound in biological systems. By functionalizing N3-Cit DCHA with imaging probes, researchers can gain insights into drug distribution, receptor binding, and tissue penetration, which is essential for the development of more effective therapies. Additionally, its specificity for certain receptors or enzymes enables its use in diagnostic imaging for detecting diseases, such as cancer, where such biomarkers are overexpressed.

Finally, N3-Cit DCHA shows promise in the development of targeted delivery vehicles for nucleic acid-based therapies, such as gene therapy or RNA interference (RNAi) technologies. The citrulline moiety can be used to facilitate the transport of nucleic acids to specific cell types, enhancing the precision and effectiveness of gene editing or silencing treatments. By conjugating N3-Cit DCHA with siRNA, mRNA, or CRISPR/Cas9 components, this compound can help deliver the therapeutic nucleic acids directly to the intended cells, improving the efficiency of gene therapies and reducing the risk of unintended side effects.

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

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