Natural Abenquines and Their Synthetic Analogues Exert Algicidal Activity against Bloom-Forming Cyanobacteria.
Abenquines are natural quinones, produced by some Streptomycetes, showing the ability to inhibit cyanobacterial growth in the 1 to 100 μM range. To further elucidate their biological significance, the synthesis of several analogues (4f-h, 5a-h) allowed us to identify some steric and electronic requirements for bioactivity. Replacing the acetyl by a benzoyl group in the quinone core and also changing the amino acid moiety with ethylpyrimidinyl or ethylpyrrolidinyl groups resulted in analogues 25-fold more potent than the natural abenquines. The two most effective analogues inhibited the proliferation of five cyanobacterial strains tested, with IC50values ranging from 0.3 to 3 μM. These compounds may be useful leads for the development of an effective strategy for the control of cyanobacterial blooms.
Department of Chemistry, Universidade Federal de Minas Gerais , Avenida Pres. Antônio Carlos, 6627, Campus Pampulha, CEP 31270-901, Belo Horizonte, MG, Brazil.
Amalyn
A
Nain-Perez
Department of Chemistry, Universidade Federal de Minas Gerais , Avenida Pres. Antônio Carlos, 6627, Campus Pampulha, CEP 31270-901, Belo Horizonte, MG, Brazil.|Department of Chemistry, Federal University of Viçosa , 36570-000, Viçosa, MG, Brazil.
Luiz Cláudio Almeida
0000-0002-5395-9608
LCA
Barbosa
Department of Chemistry, Federal University of Viçosa , 36570-000, Viçosa, MG, Brazil.
Célia Regina Álvares
CRÁ
Maltha
Department of Life Science and Biotechnology, University of Ferrara , Via L. Borsari 46, I-44121 Ferrara, Italy.
Giuseppe
G
Forlani
D029741:Brassica rapa / Q000187:drug effects / Q000254:growth & development; D000458:Cyanobacteria / Q000737:chemistry / Q000187:drug effects / Q000235:genetics; D004305:Dose-Response Relationship, Drug; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D012275:Oryza / Q000187:drug effects / Q000254:growth & development; D011809:Quinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013302:Streptomyces / Q000737:chemistry*; D013329:Structure-Activity Relationship
D011809:Quinones