Name: Mal-Ala-Ala-PAB-PNP
Brand: BOC Sciences
Rating: 5 (1 reviews)

IUPAC Name

[4-[[(2S)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]propanoyl]amino]propanoyl]amino]phenyl]methyl (4-nitrophenyl) carbonate

Canonical SMILES

CC(C(=O)NC(C)C(=O)NC1=CC=C(C=C1)COC(=O)OC2=CC=C(C=C2)[N+](=O)[O-])NC(=O)CCCCCN3C(=O)C=CC3=O

InChI

InChI=1S/C30H33N5O10/c1-19(31-25(36)6-4-3-5-17-34-26(37)15-16-27(34)38)28(39)32-20(2)29(40)33-22-9-7-21(8-10-22)18-44-30(41)45-24-13-11-23(12-14-24)35(42)43/h7-16,19-20H,3-6,17-18H2,1-2H3,(H,31,36)(H,32,39)(H,33,40)/t19-,20-/m0/s1

InChIKey

GEMSBDIHVHIIDT-PMACEKPBSA-N

Mal-Ala-Ala-PAB-PNP is a versatile conjugate used in the design of prodrug systems for targeted therapy, particularly in cancer treatment. The compound consists of a malonic acid (Mal) group, linked to two alanine (Ala) residues, a PAB (para-aminobenzyl) spacer, and a PNP (p-nitrophenyl) group. The structure is engineered to release the active drug only in the presence of specific enzymes or conditions within the tumor microenvironment. The alanine residues serve as a recognition site for certain enzymes, which cleave the prodrug, activating the cytotoxic agent. This prodrug strategy allows for the selective release of the therapeutic drug at the tumor site, reducing systemic toxicity and enhancing therapeutic efficacy by concentrating the action of the drug where it is most needed.

Another significant application of Mal-Ala-Ala-PAB-PNP is in the development of targeted chemotherapy strategies. The PNP group can be conjugated to potent chemotherapeutic agents, such as cytotoxic drugs or small molecules, forming a prodrug that remains inert during circulation. The Mal-Ala-Ala-PAB linker ensures that the prodrug is stable in the bloodstream, preventing premature activation. Upon reaching the target tissue, the prodrug is enzymatically cleaved by specific enzymes overexpressed in cancer cells, thus releasing the active drug precisely at the tumor site. This approach not only improves the drug's therapeutic index but also reduces off-target side effects that are common in traditional chemotherapy treatments.

Mal-Ala-Ala-PAB-PNP is also being explored for its applications in the field of drug delivery systems. The compound can be incorporated into various drug delivery vehicles, such as nanoparticles or liposomes, to enable targeted and controlled release of therapeutic agents. By attaching the Mal-Ala-Ala-PAB-PNP prodrug to these delivery systems, drugs can be delivered specifically to the site of disease, such as cancerous tissue or inflammatory lesions. This targeted delivery improves the bioavailability of the drug at the disease site while minimizing exposure to healthy tissues, thus improving the safety profile and effectiveness of the treatment. This application is particularly relevant for treating localized conditions where targeted drug delivery can significantly enhance treatment outcomes.