Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones

Author(s):Show less -

Polaquini, Carlos R. ^[1] ; Torrezan, Guilherme S. ^[1] ; Santos, Vanessa R. ^[2] ; Nazare, Ana C. ^[1] ; Campos, Debora L. ^[3] ; Almeida, Laiza A. ^[1] ; Silva, Isabel C. ^[3] ; Ferreira, Henrique ^[4] ; Pavan, Fernando R. ^[3] ; Duque, Cristiane ^[2] ; Regasini, Luis O. ^[1]

Affiliation

^[1] Sao Paulo State Univ Unesp, Inst Biosci Humanities & Exact Sci, Dept Chem & Environm Sci, Lab Green & Med Chem, BR-15054000 Sao Jose Do Rio Preto, SP - Brazil

^[2] Sao Paulo State Univ Unesp, Sch Dent, Dept Pediat Dent & Publ Hlth, BR-16015050 Aracatuba, SP - Brazil

^[3] Sao Paulo State Univ Unesp, Sch Pharmaceut Sci, Dept Biol Sci, BR-14800903 Aracatuba, SP - Brazil

^[4] Sao Paulo State Univ UNESP, Inst Biosci, Dept Biochem & Microbiol, BR-13506900 Rio Claro, SP - Brazil

• Document type: Journal article
• Source: Molecules; v. 22, n. 10 OCT 2017.
• Web of Science Citations: 7

Abstract

Cinnamaldehyde is a natural product with broad spectrum of antibacterial activity. In this work, it was used as a template for design and synthesis of a series of 17 cinnamylideneacetophenones. Phenolic compounds 3 and 4 exhibited MIC (minimum inhibitory concentration) and MBC (minimum bactericidal concentration) values of 77.9 to 312 mu M against Staphylococcus aureus, Streptococcus mutans, and Streptococcus sanguinis. Compounds 2, 7, 10, and 18 presented potent effects against Mycobacterium tuberculosis (57.2 mu M <= MIC <= 70.9 mu M). Hydrophilic effects caused by substituents on ring B increased antibacterial activity against Gram-positive species. Thus, log P-o/w were calculated by using high-performance liquid chromatography-photodiode array detection (HPLC-PDA) analyses, and cinnamylideneacetophenones presented values ranging from 2.5 to 4.1. In addition, the effects of 3 and 4 were evaluated on pulmonary cells, indicating their moderate toxicity (46.3 mu M <= IC50 <= 96.7 mu M) when compared with doxorubicin. Bioactive compounds were subjected to in silico prediction of pharmacokinetic properties, and did not violate Lipinski's and Veber's rules, corroborating their potential bioavailability by an oral route. (AU)

• FAPESP's process: 14/18330-0 - Synthesis and biological evaluation of curcumin-cinnamaldehyde hybrids as bacterial cell division inhibitors
• Grantee: Luis Octávio Regasini
• Support type: Regular Research Grants
• FAPESP's process: 16/06401-5 - Preparation and Biologica Evaluation of Curcumin-Cinnamaldehyde as Bacterial Cell Division Inhibitor: Cinnamylideneacetophenones
• Grantee: Laíza Araujo de Almeida
• Support type: Scholarships in Brazil - Scientific Initiation