Name: Mal-Sulfo-DBCO
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

Sulfo DBCO-Maleimide

IUPAC Name

Canonical SMILES

C1C2=CC=CC=C2C#CC3=CC=CC=C3N1C(=O)CCNC(=O)C(CNC(=O)CCN4C(=O)C=CC4=O)S(=O)(=O)O

InChI

InChI=1S/C28H26N4O8S/c33-24(14-16-31-25(34)11-12-26(31)35)30-17-23(41(38,39)40)28(37)29-15-13-27(36)32-18-21-7-2-1-5-19(21)9-10-20-6-3-4-8-22(20)32/h1-8,11-12,23H,13-18H2,(H,29,37)(H,30,33)(H,38,39,40)

InChIKey

IQQMMWCHYXQNOT-UHFFFAOYSA-N

Solubility

10 mm in DMSO

Appearance

Solid

Shelf Life

0-4°C for short term (days to weeks), or -20°C for long term (months).

Shipping

Room temperature

Storage

Store at -20 °C, keep in dry and avoid sunlight.

Form

Solid

Mal-Sulfo-DBCO is a highly specialized chemical compound commonly used in bioconjugation applications, particularly for the synthesis of antibody-drug conjugates (ADCs) and other targeted therapies. The maleimide (Mal) group enables efficient conjugation to thiol-containing molecules, such as antibodies or peptides, ensuring precise attachment to the target biomolecules. The sulfo-DBCO (sulfonated dibenzocyclooctyne) is a highly reactive functional group that facilitates the strain-promoted alkyne-azide cycloaddition (SPAAC) reaction. This reaction is widely used for click chemistry, providing a versatile and efficient method for attaching drugs, imaging agents, or other functional molecules to biologically relevant targets without the need for toxic catalysts. The sulfo group enhances the solubility of the compound in aqueous environments, improving its use in biological systems.

One of the key applications of Mal-Sulfo-DBCO is in the development of targeted drug delivery systems, particularly in the context of antibody-drug conjugates (ADCs). The compound allows for the efficient coupling of a therapeutic drug to a monoclonal antibody or peptide, which can then selectively target specific cells, such as cancer cells. The SPAAC reaction ensures that the drug is conjugated in a site-specific manner, avoiding non-specific interactions and minimizing off-target effects. By using Mal-Sulfo-DBCO in ADC design, the therapeutic efficacy is significantly enhanced, as the cytotoxic drug is delivered directly to the cancer cells, reducing systemic toxicity and improving overall treatment outcomes.

Mal-Sulfo-DBCO also plays a critical role in the development of peptide-drug conjugates (PDCs), which are increasingly used for targeted therapies. The sulfo-DBCO group provides a means of conjugating drugs or imaging agents to peptides, which can specifically recognize tumor-associated receptors or other disease biomarkers. This targeted approach allows for more precise drug delivery to disease sites, such as tumors, while minimizing damage to healthy tissues. The compound’s solubility properties make it suitable for use in complex biological environments, ensuring that PDCs remain stable and effective during circulation and administration.

Another important application of Mal-Sulfo-DBCO is in molecular imaging, where it is used to attach imaging agents, such as fluorescent dyes or radiolabeled molecules, to antibodies or peptides. This enables the precise visualization of disease biomarkers in vivo. The SPAAC reaction allows for a clean and efficient conjugation of imaging agents, which can then be used for diagnostic purposes, such as detecting tumors or monitoring treatment progress. The sulfonated group improves the solubility of the conjugates, enhancing their bioavailability and ensuring better resolution and sensitivity in imaging studies.