6328-28-5

Usage

Uses

Used in Pharmaceutical Industry:
2-[(4-nitrophenyl)sulfonylamino]pentanedioic acid is used as a chemical intermediate for the development of drugs for various therapeutic purposes. Its nitro group and sulfonylamino group make it a potential candidate for further functionalization and modification to create new derivatives with desired properties and activities.
Used in Chemical Research:
2-[(4-nitrophenyl)sulfonylamino]pentanedioic acid is used as a starting material in the synthesis of other organic compounds. Its unique structure and functional groups allow for the exploration of new chemical reactions and the development of novel compounds with potential applications in various fields.

InChI:InChI=1/C11H12N2O8S/c14-10(15)6-5-9(11(16)17)12-22(20,21)8-3-1-7(2-4-8)13(18)19/h1-4,9,12H,5-6H2,(H,14,15)(H,16,17)

Upstream product

• 56-86-0 L-glutamic acid 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 

Downstream Products

• 108272-49-7 (2S)-5-amino-5-oxo-2-[(nitrobenzene-4-ylsulfonyl)amino]pentanoic acid 
• 114967-20-3 (2S)-5-oxo-2-[(nitrobenzene-4-yl sulfonyl)amino]-5-(ethylamino)pentanoic acid 
• 6328-29-6 N-sulfanilyl-L-glutamic acid 

Relevant academic research and scientific papers

A pentanoic acid derivative targeting matrix metalloproteinase-2 (MMP-2) induces apoptosis in a chronic myeloid leukemia cell line

Depending on our previous observations, some compounds of pentanoic acid were designed and synthesized. Characterization of the synthesized compounds was done by mass, NMR and IR spectroscopy as well as elemental analysis. Among the synthesized molecules, (2S)-5-oxo-2-[(nitrobenzene-4-yl sulfonyl) amino]-5-(pentylamino) pentanoic acid (Cpd 11) was found as a lead and potent inhibitor of matrix metalloproteinase-2 (MMP-2). Molecular modeling and enzyme inhibition studies were done to confirm the interaction or inhibitory potential of this compound. Thereafter, the biological screening was done through cytotoxicity, anti-invasion and apoptosis-related assays. Docking analysis revealed that Cpd 11 interacted with the target molecule MMP-2 and with MMP-9. However, enzyme inhibition assay showed 3-fold MMP-2 inhibition compared to MMP-9. Cytotoxicity assay showed the inhibitory potential of Cpd 11 against K562 cell line having IC50 value of 17.9 ± 0.01 μM after 48 h of incubation. The cell death was apoptotic in nature as revealed from the annexin V and sub-G1 cell cycle arrest assay. Besides this, Cpd 11 also exhibited dose dependent anti-invasive activity into K562 cell line. On the other hand, flow cytometry and western blot data revealed Cpd 11 induced downregulation of MMP-2 in K562 cell line after 48 h of incubation that might be linked with the anti-invasive and apoptotic activity furthermore. Therefore, the overall results validated each method and make this molecule as a potent MMP-2 inhibitor that blocked the invasion and could bring apoptosis at later stages in K562 cells sparing the normal ones.