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Chemical Structure of Retro-2, a Compound That Protects Cells Against Ribosome-Inactivating Proteins

Chemical Structure of Retro-2, a Compound That Protects Cells Against Ribosome-Inactivating Proteins

Jewn Giew Park, Jennifer Nielsen Kahn, Nilgun E Tumer, Yuan-Ping Pang

Sci Rep. 2012;2:631.

PMID: 22953052

Abstract:

Shiga-like toxins and ricin are ribosome-inactivating proteins (RIPs) that are lethal to mammals and pose a global health threat. No clinical vaccines or therapeutics currently exist to protect against these RIPs. Two small molecules (Retro-1 and Retro-2) were discovered with high-throughput screening and reported for their protection of cells against RIPs. Of great significance, Retro-2, reported as (E)-2-(((5-methylthiophen-2-yl)methylene)amino)-N-phenylbenzamide, fully protected mice from lethal nasal challenge with ricin. Herein, we report studies showing that the chemical structure of Retro-2 is (±)-2-(5-methylthiophen-2-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one rather than (E)-2-(((5-methylthiophen-2-yl)methylene)amino)-N-phenylbenzamide. The latter is an achiral molecule that converts spontaneously to the former, which is a racemate and showed cell protection against RIPs. This calls for attention to (±)-2-(5-methylthiophen-2-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one as a promising RIP inhibitor and for chemical characterization of drug leads obtained from high-throughput screens.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
IAR42415426	Retro-2			Price

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