2. Academic Validation
  3. Synthesis and evaluation of in vivo antioxidant, in vitro antibacterial, MRSA and antifungal activity of novel substituted isatin N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazones

Synthesis and evaluation of in vivo antioxidant, in vitro antibacterial, MRSA and antifungal activity of novel substituted isatin N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazones

  • Eur J Med Chem. 2016 Nov 10:123:532-543. doi: 10.1016/j.ejmech.2016.07.074.
Nguyen Dinh Thanh 1,  Nguyen Thi Kim Giang 2,  Tran Ha Quyen 3,  Doan Thi Huong 3,  Vu Ngoc Toan 4
Affiliations

Affiliations

  • 1 Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Viet Nam. Electronic address: nguyendinhthanh@hus.edu.vn.
  • 2 Lab of Profession Chemistry, Institute of Biochemical Technology and Profession Documents, General Department 4 (Ministry of Public Security), 80 Tran Quoc Hoan, Cau Giay, Ha Noi, Viet Nam.
  • 3 Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Viet Nam.
  • 4 Institute for Chemistry and Materials, Military Institute of Science and Technology, 17 Hoang Sam, Cau Giay, Ha Noi, Viet Nam.
PMID: 27517802 DOI: 10.1016/j.ejmech.2016.07.074
Abstract

Some new isatin N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazones 4a-t with different substituents at 1-, 5- and 7-positions of isatin ring have been synthesized by reaction of N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazide 2 with corresponding isatins 3a-t. Compounds 4a-t were evaluated in vivo for antioxidant activity and in vitro for anti-microorganism activities. The MIC values were found for Gram positive bacteria (MIC = 1.56-6.25 μM), for Gram negative bacteria (MIC = 12.5 μM), and for fungi Aspergillus niger (MIC = 3.12-12.5 μM), Fusarium oxysporum (MIC = 6.25-12.5 μM) and Saccharomyces cerevisiae (MIC = 6.25-12.5 μM). Regarding the antioxidant activity, the SOD, GHS-Px and catalase activities of 4c-i and 4m-r were MIC = 10.57-10.85, 0.27-0.93 and 345.45-399.75 unit/mg protein, respectively. Compounds 4e-h had MIC values of 0.78, 1.56, and 3.12 μM for three clinical MRSA isolates. Compound 4e showed the selective cytotoxic effects against some Cancer (LU-1, HepG2, MCF7, P338, SW480, KB) cell lines and normal fibroblast cell line NIH/3T3.

Keywords

Antibacterial; Antifungal; Antioxidant activity; Cytotoxic effects; D-glucose; Isatins; Methicillin-resistant Staphylococcus aureus; Microwave-assisted synthesis; Thiosemicarbazones.

Figures