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A facile preparation and crystal structure of romipeptide A

Abstract

A double disulfide tethering depsipeptide dimer, romipeptide A (1) was prepared by NaOH catalyzed dimerization of romidepsin. Its structure was determined by analysis of NMR and HR-ESI-MS data as well as single crystal X-ray diffraction. Bioassay results showed that 1 exhibited good cytotoxic activity against two tumor cell lines B16 and HCT116. This study reported the single crystal data of 1 for the first time. The facile preparation of 1 afforded enough amount for its further biological evaluations.

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References

  1. VanderMolen KM, McCulloch W, Pearce CJ, Oberlies NH. Romidepsin (Istodax, NSC 630176, FR901228, FK228, depsipeptide): a natural product recently approved for cutaneous T-cell lymphoma. J Antibiot. 2011;64:525–31.

    Article  CAS  Google Scholar 

  2. Furumai R, Matsuyama A, Kobashi N, Lee KH, Nishiyama M, Nakajima H, et al. FK228 (depsipeptide) as a natural prodrug that inhibits class I HDACs. Cancer Res. 2002;62:4916–21.

    CAS  PubMed  Google Scholar 

  3. Mullard A. 2011 FDA drug approvals. Nat Rev Drug Disco. 2012;11:91–94.

    Article  CAS  Google Scholar 

  4. ClinicalTrials.gov [Internet]. US National Institutes of health. [Cited August, 2021]. Available from: http://clinicaltrials.gov/.

  5. Wang C, Henkes LM, Doughty LB, He M, Wang D, Meyer-Almes FJ, et al. Thailandepsins: bacterial products with potent histone deacetylase inhibitory activities and broad-spectrum antiproliferative activities. J Nat Prod. 2011;74:2031–8.

    Article  CAS  Google Scholar 

  6. Masuoka Y, Nagai A, Shin-ya K, Furihata K, Nagai K, Suzuki K, et al. Spiruchostatins A and B, novel gene expression-enhancing substances produced by Pseudomonas sp. Tetrahedron Lett. 2001;42:41–44.

    Article  CAS  Google Scholar 

  7. Zhou Z, Wang X, Zhang H, Sun J, Zheng L, Liu H, et al. Chromopeptide A, a highly cytotoxic depsipeptide from the marine sediment-derived bacterium Chromobacterium sp. Hs-13-94. Acta Pharm Sin B. 2015;5:62–66.

    Article  Google Scholar 

  8. Xiong L, Chen CA, Min TL, Hu HF. Romipeptides A and B, two new romidepsin derivatives isolated from Chromobacterium violaceum No.968 and their antitumor activities in vitro. Chin J Nat Med. 2019;17:155–60.

    PubMed  Google Scholar 

  9. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst. 1990;82:1107–12.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research was financially supported by the Key Research and Development Program of Zhejiang Province (Grant No: 2020C02028) and Taizhou Science and Technology Plan Project (21nya24).

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Correspondence to Ji-dong Wang or Wen-sheng Xiang.

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Zhang, H., Qi, H., Duan, Wk. et al. A facile preparation and crystal structure of romipeptide A. J Antibiot 75, 48–50 (2022). https://doi.org/10.1038/s41429-021-00487-2

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