Leishmanicidal activity of combretastatin analogues and heteroanalogues

Rey, Benedicto del; Ramos, Angel C.; Caballero, Esther; Inchaustti, Alba; Yaluff, Gloria; Medarde, Manuel; Arlas, Antonieta Rojas de; Feliciano, Arturo San

doi:10.1016/s0960-894x(99)00453-9

Cited by 24 publications

(4 citation statements)

References 12 publications

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“…The activity of the compounds was evaluated after 72 h by observation of a drop of each culture with a microscope and compared with control cells. Assays were performed in triplicate (Del Rey et al, 1999). Amphotericin B and pentamidine were used as reference compounds.…”

Section: Methodsmentioning

confidence: 99%

A new antifungal and antiprotozoal depside from the andean lichen Protousnea poeppigii

Schmeda-Hirschmann

Tapia

Lima

et al. 2007

Phytotherapy Research

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Extracts from the Andean lichens Protousnea poeppigii and Usnea florida displayed antimicrobial activity against the pathogenic fungi Microsporum gypseum, Trichophyton mentagrophytes and T. rubrum with MIC values between 50 and 100 microg/mL. From the active extracts, four main metabolites were isolated and identified as the new depside, isodivaricatic acid, and the known metabolites 5-propylresorcinol, divaricatinic acid and usnic acid. Isodivaricatic acid and divaricatinic acid presented antifungal effect towards M. gypseum with a MIC of 50 microg/mL and against T. mentagrophytes and T. rubrum and with MIC values of 50 and 100 microg/mL, respectively. The new isodivaricatic acid was active towards Leishmania amazonensis, Leishmania brasiliensis and Leishmania infantum promastigotes with 100% lysis at 100 microg/mL.The activity of the new compound decreased on acetylation of the hydroxy groups as well as on methylation of the acid function. The structures were elucidated by spectroscopic means. The spectroscopic data of isodivaricatic acid are presented here for the first time.

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Section: Methodsmentioning

confidence: 99%

A new antifungal and antiprotozoal depside from the andean lichen Protousnea poeppigii

Schmeda-Hirschmann

Tapia

Lima

et al. 2007

Phytotherapy Research

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“…The activity of compounds was evaluated after 72 h by optical observation of a drop of each culture with a microscope and compared with control cells. Assays to assess the drug concentration required to inhibit parasite growth were performed in triplicate (Del Rey et al 1999).…”

Section: Leishmanicidal Activity In-vitromentioning

confidence: 99%

Cryptofolione derivatives from Cryptocarya alba fruits

Schmeda-Hirschmann

Astudillo

Codina

et al. 2001

Journal of Pharmacy and Pharmacology

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Cryptofolione (1) and the new cryptofolione derivative 6-(4,6-dimethoxy-8-phenyl-octa-1,7-dienyl)-4-hydroxy-tetrahydro-pyran-2-one (2) were isolated from the fruits of Cryptocarya alba. The structures were elucidated by spectroscopic methods. Cryptofolione showed activity towards Trypanosoma cruzi trypomastigotes, reducing their number by 77% at 250 microg mL(-1). Cryptofolione showed moderate cytotoxicity in both macrophages and T. cruzi amastigotes. It also displayed a mild inhibitory effect on the promastigote form of Leishmania spp. As both cytotoxic and trypanocidal effects are similar, the compound presented little selectivity in our assay models.

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“…Combretastatins and heterocombretastatins have previously been tested for in vitro activity in three different species of Leishmania ( L. amazonensis , L. braziliensis and L. donovani ). 9 Two of the most active, SAAS-41 and SAAS-59 (Figure 2) were also tested for in vivo activity in mice infected with amastigotes of the species L. amazonensis , resulting in very significant reductions in lesion size and parasite load. 10 …”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4

Santos¹,

Prado²,

Carvalho³

et al. 2013

Quím. Nova

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We extended our previous exploration of sulfur bridges as bioisosteric replacements for atoms forming the bridge between the aromatic rings of combretastatin A-4. Employing coupling reactions between 5-iodo-1,2,3-trimethoxybenzene and substituted thiols, followed by oxidation to sulfones with m-CPBA, different locations for attaching the sulfur atom to ring A through the synthesis of nine compounds were examined. Antitubulin activity was performed with electrophoretically homogenous bovine brain tubulin, and activity occurred with the 1,2,3-trimethoxy-4-[(4-methoxyphenyl)thio]benzene (12), while the other compounds were inactive. The compounds were also tested for leishmanicidal activity using promastigote forms of Leishmania braziliensis (MHOM/BR175/M2904), and the greatest activity was observed with 1,2,3-trimethoxy-4-(phenylthio)benzene (10) and 1,2,3-trimethoxy-4-[(4-methoxyphenyl) sulfinyl]benzene (15).

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Leishmanicidal activity of combretastatin analogues and heteroanalogues

Cited by 24 publications

References 12 publications

A new antifungal and antiprotozoal depside from the andean lichen Protousnea poeppigii

A new antifungal and antiprotozoal depside from the andean lichen Protousnea poeppigii

Cryptofolione derivatives from Cryptocarya alba fruits

Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4

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