Name: Mal-Val-Ala-PABA-cGAMP
Brand: BOC Sciences
Rating: 5 (1 reviews)

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IUPAC Name

[4-[[(2S)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]-3-methylbutanoyl]amino]propanoyl]amino]phenyl]methyl N-[9-[(1S,6R,8R,9R,10S,15R,17R,18R)-17-(2-amino-6-oxo-1H-purin-9-yl)-3,9,12,18-tetrahydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3λ5,12λ5-diphosphatricyclo[13.3.0.06,10]octadecan-8-yl]purin-6-yl]carbamate

Canonical SMILES

CC(C)C(C(=O)NC(C)C(=O)NC1=CC=C(C=C1)COC(=O)NC2=C3C(=NC=N2)N(C=N3)C4C(C5C(O4)COP(=O)(OC6C(COP(=O)(O5)O)OC(C6O)N7C=NC8=C7N=C(NC8=O)N)O)O)NC(=O)CCCCCN9C(=O)C=CC9=O

InChI

InChI=1S/C46H56N14O20P2/c1-21(2)30(54-27(61)7-5-4-6-14-58-28(62)12-13-29(58)63)41(67)52-22(3)40(66)53-24-10-8-23(9-11-24)15-74-46(69)55-37-31-38(49-18-48-37)59(19-50-31)43-33(64)35-25(77-43)16-75-82(72,73)80-36-26(17-76-81(70,71)79-35)78-44(34(36)65)60-20-51-32-39(60)56-45(47)57-42(32)68/h8-13,18-22,25-26,30,33-36,43-44,64-65H,4-7,14-17H2,1-3H3,(H,52,67)(H,53,66)(H,54,61)(H,70,71)(H,72,73)(H3,47,56,57,68)(H,48,49,55,69)/t22-,25+,26+,30-,33+,34+,35+,36+,43+,44+/m0/s1

InChIKey

LYBBNXLPTBIBMH-XMLVYOPNSA-N

Appearance

Light yellow to yellow Solid

Mal-Val-Ala-PABA-cGAMP is a multifunctional compound with significant applications in targeted drug delivery and immune modulation. The maleimide (Mal) group allows for efficient conjugation to thiol-containing biomolecules, such as proteins, antibodies, or peptides, making it an excellent choice for bioconjugation strategies. The inclusion of the Val-Ala-PABA peptide sequence provides a spacer that can enhance the solubility and flexibility of the conjugate, while also influencing the overall pharmacokinetics. The addition of cGAMP (cyclic GMP-AMP), a well-known immune-stimulatory molecule, enables this compound to engage in immune modulation, making it useful in applications like cancer immunotherapy and vaccine development.

One of the key applications of Mal-Val-Ala-PABA-cGAMP is in the development of immune-activating antibody-drug conjugates (ADCs). By linking cGAMP to an antibody or peptide through the maleimide group, this conjugate can leverage the immune-stimulatory properties of cGAMP to activate immune responses against cancer cells. The conjugation of cGAMP to antibodies allows for targeted delivery of the immune activator to tumor sites, where it can help activate the STING (stimulator of interferon genes) pathway, stimulating an immune response. The inclusion of Val-Ala-PABA serves as a flexible linker, optimizing the solubility and stability of the conjugate, which can improve its efficacy in therapeutic applications.

Another important use of Mal-Val-Ala-PABA-cGAMP is in the development of peptide-based vaccines for cancer and infectious diseases. The incorporation of cGAMP into the vaccine platform can enhance the body’s immune response by promoting the activation of the STING pathway, which is crucial for the induction of both innate and adaptive immune responses. The maleimide group facilitates the efficient conjugation of the vaccine components to the peptide carriers, while the Val-Ala-PABA linker ensures that the conjugates maintain stability and bioavailability. This strategy offers a targeted approach to vaccine delivery, improving efficacy and reducing unwanted side effects.

Mal-Val-Ala-PABA-cGAMP can also be used in diagnostic applications, particularly for enhancing the sensitivity and specificity of immunoassays. By conjugating cGAMP to antibodies or peptides designed to bind specific biomarkers, this compound can be employed in assays that detect diseases, such as cancer or viral infections. The immune-stimulatory effects of cGAMP can increase the sensitivity of the assay by boosting the immune response to the target biomarker. Furthermore, the linker components provide the necessary stability and solubility, improving the performance of the assay in clinical and research settings.