Structure-activity relationship of leucyladenylate sulfamate analogues as leucyl-tRNA synthetase (LRS)-targeting inhibitors of Mammalian target of rapamycin complex 1 (mTORC1)

  • Bioorg Med Chem. 2019 Mar 15;27(6):1099-1109. doi: 10.1016/j.bmc.2019.01.037.
Suyoung Yoon  1 Sung-Eun Kim  1 Jong Hyun Kim  2 Ina Yoon  2 Phuong-Thao Tran  3 Jihyae Ann  1 Changhoon Kim  1 Woong Sub Byun  1 Sangkook Lee  1 Sunghoon Kim  4 Jiyoun Lee  5 Jeewoo Lee  6
Affiliations
  • 1. Laboratory of Medicinal Chemistry, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.
  • 2. Medicinal Bioconvergence Research Center, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.
  • 3. Department of Medicinal Chemistry, Hanoi University of Pharmacy, 13-15 Le Thanh Tong, Hoan Kiem, Hanoi, Viet Nam.
  • 4. Medicinal Bioconvergence Research Center, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea; Department of Molecular Medicine and Biopharmaceutical Sciences, Graduate School of Convergence Science and Technology, Seoul National University, Seoul 08826, Republic of Korea.
  • 5. Department of Global Medical Science, Sungshin University, Seoul 01133, Republic of Korea. Electronic address: [email protected].
  • 6. Laboratory of Medicinal Chemistry, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea. Electronic address: [email protected].
Abstract

Leucyl-tRNA synthetase (LRS) plays an important role in amino acid-dependent mTORC1 signaling, which is known to be associated with cellular metabolism and proliferation. Therefore, LRS-targeting small molecules that can suppress mTORC1 activation may provide an alternative strategy to current Anticancer therapy. In this work, we developed a library of leucyladenylate sulfate analogues by extensively modifying three different pharmacophoric regions comprising adenine, ribose and leucine. Several effective compounds were identified by cell-based mTORC1 activation assays and further tested for Anticancer activity. The selected compounds mostly exhibited selective cytotoxicity toward five different Cancer cell lines, supporting the hypothesis that the LRS-mediated mTORC1 pathway is a promising alternative target to current therapeutic approaches.

Keywords
Anticancer agents; LRS; Leucyl-tRNA synthetase; Leucyladenylate; mTORC1 inhibitor.