Details

Autor(en) / Beteiligte

• Pereira, A.C.
• Magalhães, L.G.
• Gonçalves, U.O.
• Luz, P.P.
• Moraes, A.C.G.
• Rodrigues, V.
• da Matta Guedes, P.M.
• da Silva Filho, A.A.
• Cunha, W.R.
• Bastos, J.K.
• Nanayakkara, N.P.D.
• e Silva, M.L.A.

Titel

Schistosomicidal and trypanocidal structure–activity relationships for (±)-licarin A and its (−)- and (+)-enantiomers

Ist Teil von

• Phytochemistry (Oxford), 2011-08, Vol.72 (11-12), p.1424-1430

Ort / Verlag

Amsterdam: Elsevier Ltd

Erscheinungsjahr

2011

Quelle

MEDLINE

Beschreibungen/Notizen

• The schistosomicidal and trypanocidal activities of (±)-licarin A (1) and its enantiomers, (−)-licarin A (2) and (+)-licarin A (3), were evaluated against both Shistosoma mansoni adult worms and trypomastigote forms of Trypanosoma cruzi. For schistosomicidal activity, the racemic mixture (1) was more effective than the enantiomers (2 and 3). However, enantiomer 2 was more effective than enantiomer 3. For trypanocidal activity, enantiomer 2 was the most effective. [Display omitted] ► Synthesis of (±)-licarin, its resolution and antiparasitary activity. ► (±)-Licarin A was resolved by chiral HPLC furnishing its (−) and (+) enantiomers. ► Schistosomicidal and trypanocidal activities were studied in vitro. ► For Shistosoma mansoni (±)-licarin was the most active. ► For Trypanosoma cruzi (−)-licarin was the most active. (±)-Licarin A (1) was obtained by oxidative coupling, and its enantiomers, (−)-licarin A (2) and (+)-licarin A (3), were resolved by chiral HPLC. Schistosomicidal and trypanocidal activities of these compounds were evaluated in vitro against Schistosoma mansoni adult worms and trypomastigote forms of Trypanosoma cruzi. The racemic mixture (1) displayed significant schistosomicidal activity with an LC50 value of 53.57μM and moderate trypanocidal activity with an IC50 value of 127.17μM. On the other hand, the (−)-enantiomer (2), displaying a LC50 value of 91.71μM, was more active against S. mansoni than the (+)-enantiomer (3), which did not show activity. For the trypanocidal assay, enantiomer 2 showed more significant activity (IC50 of 23.46μM) than enantiomer 3, which showed an IC50 value of 87.73μM. Therefore, these results suggest that (±)-licarin A (1) and (−)-licarin A (2) are promising compounds that could be used for the development of schistosomicidal and trypanocidal agents.