ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis of new indirubin derivatives and their in vitro anticancer activity

Dan Trong Nguyen, Giang Nguyen Truong, Truong Van Vuong, Tai Nguyen Van, Cuong Nguyen Manh, Cuong To Dao, Thuy Dinh Thi Thuy, Chinh Luu Van, and Vu Tran Khac

Vietnam-Russia Tropical Center, Hanoi, Vietnam

E-mail: chinhluuvan@gmail.com

Abstract: The opening of epoxy rings from (2′Z)-N-1-(oxiran-2-ylmethyl)indirubin (2) and (2′Z-3′E)-indirubin-3ʹ-[O-oxiran-2-ylmethyl)oxime] (6) with thiols gave 17 new derivatives of indirubin in good yields. Their structures were elucidated by 1D-, 2D-NMR and HRMS spectra. Screening for anticancer activity was performed with four human cancer cell lines: SW480, LU-1, HepG2 and HL-60 in comparison with indirubin, indirubin-3′-oxime and 6-mercaptopurine. The results showed that cytotoxic and anti-proliferative activities of five derivatives were found in the range of 1.35–19.24 µM. Among synthesized derivatives, 4f showed the strongest activity against all four tested cancer cell lines with IC₅₀ values of 1.65, 2.21, 1.90 and 1.35 µM, respectively.

Keywords: Indirubin ; Indirubin-3′-oxime ; 6-mercaptopurine ; Cytotoxic 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-018-0659-4

Chemical Papers 73 (5) 1083–1092 (2019)