Design, synthesis and biological evaluation of novel Schiff base-bridged tetrahydroprotoberberine triazoles as a new type of potential antimicrobial agents

MedChemComm
2017.0

Abstract

A series of novel Schiff base-bridged tetrahydroprotoberberine (THPB) triazoles were designed, synthesized and characterized for the first time. Antimicrobial assay showed that some of the prepared compounds exerted stronger antibacterial and antifungal activities than the reference drugs. Especially, THPB triazole <b>7a</b> gave low MIC values of 0.5, 1 and 2 μg mL<sup>-1</sup> against <i>B. yeast</i>, <i>M. luteus</i> and MRSA, respectively. Further experiments indicated that the highly active molecule <b>7a</b> was able to rapidly kill the MRSA strain and did not trigger the development of bacterial resistance even after 14 passages. The preliminary exploration for the antimicrobial mechanism revealed that compound <b>7a</b> could effectively intercalate into calf thymus DNA to form a <b>7a</b>-DNA supramolecular complex, and its Zn<sup>2+</sup> complex had the ability to directly cleave pUC19 DNA, which suggested that compound <b>7a</b> might be a potentially dual-targeting antibacterial molecule. It was also found that compound <b>7a</b> could be efficiently stored and carried by human serum albumin (HSA), and the hydrophobic interactions and hydrogen bonds played important roles in the transportation of HSA to the active molecule <b>7a</b>.

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