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DBCO-C6-acid

  CAS No.: 1425485-72-8   Cat No.: BADC-00948   Purity: >95.0% HPLC MS HNMR 4.5  

DBCO-C6-acid is a carboxylic acid-functionalized ADC linker featuring dibenzocyclooctyne for copper-free click conjugation, enhancing biocompatibility and site-specific antibody modification.

DBCO-C6-acid

Structure of 1425485-72-8

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Category
ADC Linker
Molecular Formula
C21H19NO3
Molecular Weight
333.39
Shipping
Room temperature, or blue ice upon request.
Shipping
Store at -20 °C, keep in dry and avoid sunlight.

* For research and manufacturing use only. We do not sell to patients.

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Synonyms
Azadibenzocyclooctyne acid; 6-(11,12-Didehydro-5,6-dihydrodibenzo[b,f]azocine-5-yl)-6-oxohexanoic acid
IUPAC Name
Canonical SMILES
C1C2=CC=CC=C2C#CC3=CC=CC=C3N1C(=O)CCCCC(=O)O
InChI
InChI=1S/C21H19NO3/c23-20(11-5-6-12-21(24)25)22-15-18-9-2-1-7-16(18)13-14-17-8-3-4-10-19(17)22/h1-4,7-10H,5-6,11-12,15H2,(H,24,25)
InChIKey
NIRLBCOFKPVQLM-UHFFFAOYSA-N
Density
1.3±0.1 g/cm3
Solubility
10 mm in DMSO
Flash Point
337.5±31.5 °C
Index Of Refraction
1.654
Vapor Pressure
0.0±2.0 mmHg at 25°C
Appearance
white to slight grey solid
Shelf Life
0-4°C for short term (days to weeks), or -20°C for long term (months).
Shipping
Room temperature, or blue ice upon request.
Storage
Store at -20 °C, keep in dry and avoid sunlight.
Boiling Point
634.4±55.0 °C at 760 mmHg
Biological Activity
DBCO-C6-acid is a non-cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs). DBCO-C6-acid can be used in the synthesis of carmaphycin analogues[1] . In Vitro: ADCs are comprised of an antibody to which is attached an ADC cytotoxin through an ADC linker.

DBCO-C6-acid, or DibenzoCycloOctyne-C6-acid, is a chemical compound widely recognized for its utility in bioorthogonal chemistry, a field of chemistry that enables highly specific reactions within living systems without interfering with native biochemical processes. This compound features a strained cyclooctyne structure which facilitates rapid and catalyst-free ligation with azides due to its high ring strain and electronic properties. The “C6-acid” component refers to the six-carbon linker appended with a carboxylic acid functional group, providing the compound with enhanced solubility and the ability to conjugate with various biomolecules. The high reactivity and specificity of DBCO-C6-acid make it an invaluable tool for bioconjugation techniques used extensively in molecular biology and drug development.

One of the pivotal applications of DBCO-C6-acid in drug discovery is its role in click chemistry, a technique that allows for the quick and reliable joining of small molecules to functionalize larger compounds, peptides, or proteins. This technique is especially crucial in the early stages of drug development, where researchers need to quickly generate and test large libraries of potential drug candidates. The inherent efficiency of DBCO-C6-acid in forming stable and irreversible bonds with azides means it can be used to “click” therapeutic agents onto targeting ligands with precision, creating conjugates that can better navigate biological environments or deliver drugs more selectively to diseased cells. This capability greatly enhances the drug design process by improving targeting specificity and reducing off-target effects.

Furthermore, DBCO-C6-acid is integral to the advancement of antibody-drug conjugates (ADCs), a class of targeted cancer therapies. In ADCs, a potent cytotoxic drug is linked to an antibody that specifically targets cancer cells, delivering the drug directly to the tumor site while minimizing damage to healthy tissue. The reliable bioorthogonal reactions facilitated by DBCO-C6-acid enable the efficient and site-specific attachment of drugs to antibodies, ensuring maximum therapeutic efficacy. The increased stability and reduced toxicity associated with these conjugates underscore the significance of DBCO-C6-acid in creating next-generation therapeutics that offer improved patient outcomes in oncology.

DBCO-C6-acid also finds significant application in the realm of imaging and diagnostics within drug discovery. By enabling the attachment of imaging agents to biological molecules, it facilitates the visualization and tracking of molecular processes in real time. This is invaluable for understanding disease mechanisms and assessing the pharmacokinetics and biodistribution of new drugs. The precise and robust linking capabilities of DBCO-C6-acid enhance the resolution and reliability of imaging studies, providing detailed insights into drug behavior and interaction within the body. Such contributions are critical for developing more effective diagnostics and for the preclinical evaluation of drug candidates.

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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