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Lead Identification of 8-(Methylamino)-2-oxo-1,2-dihydroquinoline Derivatives as DNA Gyrase Inhibitors: Hit-to-Lead Generation Involving Thermodynamic Evaluation.
Ushiyama, Fumihito; Amada, Hideaki; Takeuchi, Tomoki; Tanaka-Yamamoto, Nozomi; Kanazawa, Harumi; Nakano, Koichiro; Mima, Masashi; Masuko, Aiko; Takata, Iichiro; Hitaka, Kosuke; Iwamoto, Kunihiko; Sugiyama, Hiroyuki; Ohtake, Norikazu.
Afiliación
  • Ushiyama F; Chemistry Laboratories, Taisho Pharmaceutical Company Ltd., 1-403, Yoshino-Cho, Kita-Ku, Saitama, Saitama 331-9530, Japan.
  • Amada H; Chemistry Laboratories, Taisho Pharmaceutical Company Ltd., 1-403, Yoshino-Cho, Kita-Ku, Saitama, Saitama 331-9530, Japan.
  • Takeuchi T; Chemistry Laboratories, Taisho Pharmaceutical Company Ltd., 1-403, Yoshino-Cho, Kita-Ku, Saitama, Saitama 331-9530, Japan.
  • Tanaka-Yamamoto N; Chemistry Laboratories, Taisho Pharmaceutical Company Ltd., 1-403, Yoshino-Cho, Kita-Ku, Saitama, Saitama 331-9530, Japan.
  • Kanazawa H; Chemistry Laboratories, Taisho Pharmaceutical Company Ltd., 1-403, Yoshino-Cho, Kita-Ku, Saitama, Saitama 331-9530, Japan.
  • Nakano K; Pharmacology Laboratories, Taisho Pharmaceutical Company Ltd., 1-403, Yoshino-Cho, Kita-Ku, Saitama, Saitama 331-9530, Japan.
  • Mima M; Pharmacology Laboratories, Taisho Pharmaceutical Company Ltd., 1-403, Yoshino-Cho, Kita-Ku, Saitama, Saitama 331-9530, Japan.
  • Masuko A; Pharmacology Laboratories, Taisho Pharmaceutical Company Ltd., 1-403, Yoshino-Cho, Kita-Ku, Saitama, Saitama 331-9530, Japan.
  • Takata I; Pharmacology Laboratories, Taisho Pharmaceutical Company Ltd., 1-403, Yoshino-Cho, Kita-Ku, Saitama, Saitama 331-9530, Japan.
  • Hitaka K; Pharmacology Laboratories, Taisho Pharmaceutical Company Ltd., 1-403, Yoshino-Cho, Kita-Ku, Saitama, Saitama 331-9530, Japan.
  • Iwamoto K; Pharmacology Laboratories, Taisho Pharmaceutical Company Ltd., 1-403, Yoshino-Cho, Kita-Ku, Saitama, Saitama 331-9530, Japan.
  • Sugiyama H; Pharmacology Laboratories, Taisho Pharmaceutical Company Ltd., 1-403, Yoshino-Cho, Kita-Ku, Saitama, Saitama 331-9530, Japan.
  • Ohtake N; Chemistry Laboratories, Taisho Pharmaceutical Company Ltd., 1-403, Yoshino-Cho, Kita-Ku, Saitama, Saitama 331-9530, Japan.
ACS Omega ; 5(17): 10145-10159, 2020 May 05.
Article en En | MEDLINE | ID: mdl-32391502
DNA gyrase and topoisomerase IV are well-validated pharmacological targets, and quinolone antibacterial drugs are marketed as their representative inhibitors. However, in recent years, resistance to these existing drugs has become a problem, and new chemical classes of antibiotics that can combat resistant strains of bacteria are strongly needed. In this study, we applied our hit-to-lead (H2L) chemistry for the identification of a new chemical class of GyrB/ParE inhibitors by efficient use of thermodynamic parameters. Investigation of the core fragments obtained by fragmentation of high-throughput screening hit compounds and subsequent expansion of the hit fragment was performed using isothermal titration calorimetry (ITC). The 8-(methylamino)-2-oxo-1,2-dihydroquinoline derivative 13e showed potent activity against Escherichia coli DNA gyrase with an IC50 value of 0.0017 µM. In this study, we demonstrated the use of ITC for primary fragment screening, followed by structural optimization to obtain lead compounds, which advanced into further optimization for creating novel antibacterial agents.

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Tipo de estudio: Diagnostic_studies Idioma: En Revista: ACS Omega Año: 2020 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Tipo de estudio: Diagnostic_studies Idioma: En Revista: ACS Omega Año: 2020 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos