Second-generation pterocarpanquinones: synthesis and antileishmanial activity View Full Text


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Article Info

DATE

2018-11-29

AUTHORS

Viviane dos Santos Faiões, Lívia C. R. M. da Frota, Edézio Ferreira Cunha-Junior, Julio C. F. Barcellos, Thayssa Da Silva, Chaquip Daher Netto, Silvia Amaral Gonçalves Da-Silva, Alcides J. M. da Silva, Paulo R. R. Costa, Eduardo Caio Torres-Santos

ABSTRACT

BackgroundDespite the development of new therapies for leishmaniasis, among the 200 countries or territories reporting to the WHO, 87 were identified as endemic for Tegumentary Leishmaniasis and 75 as endemic for Visceral Leishmaniasis. The identification of antileishmanial drug candidates is essential to fill the drug discovery pipeline for leishmaniasis. In the hit molecule LQB-118 selected, the first generation of pterocarpanquinones was effective and safe against experimental visceral and cutaneous leishmaniasis via oral delivery. In this paper, we report the synthesis and antileishmanial activity of the second generation of pterocarpanoquinones.MethodsThe second generation of pterocarpanquinones 2a-f was prepared through a palladium-catalyzed oxyarylation of dihydronaphtalen and chromens with iodolawsone, easily prepared by iodination of lawsone. The spectrum of antileishmanial activity was evaluated in promastigotes and intracellular amastigotes of L. amazonensis, L. braziliensis, and L. infantum. Toxicity was assessed in peritoneal macrophages and selective index calculated by CC50/IC50. Oxidative stress was measured by intracellular ROS levels and mitochondrial membrane potential in treated cells.ResultsIn this work, we answered two pertinent questions about the structure of the first-generation pterocarpanquinones: the configuration and positions of rings B (pyran) and C (furan) and the presence of oxygen in the B ring. When rings B and C are exchanged, we noted an improvement of the activity against promastigotes and amastigotes of L. amazonensis and promastigotes of L. infantum. As to the oxygen in ring B of the new generation, we observed that the oxygenated compound 2b is approximately twice as active against L. braziliensis promastigotes than its deoxy derivative 2a. Another modification that improved the activity was the addition of the methylenedioxy group. A variation in the susceptibility among species was evident in the clinically relevant form of the parasite, the intracellular amastigote. L. amazonensis was the species most susceptible to novel derivatives, whilst L. infantum was resistant to most of them. The pterocarpanoquinones (2b and 2c) that possess the oxygen atom in ring B showed induction of increased ROS production.ConclusionsThe data presented indicate that the pterocarpanoquinones are promising compounds for the development of new leishmanicidal agents. More... »

PAGES

35

Identifiers

URI

http://scigraph.springernature.com/pub.10.1186/s40409-018-0174-7

DOI

http://dx.doi.org/10.1186/s40409-018-0174-7

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https://app.dimensions.ai/details/publication/pub.1110263558

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/30519257


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80 new therapies
81 novel derivatives
82 oral delivery
83 oxidative stress
84 oxyarylation
85 oxygen
86 oxygen atoms
87 paper
88 parasites
89 peritoneal macrophages
90 pertinent questions
91 pipeline
92 position
93 potential
94 presence
95 presence of oxygen
96 production
97 promastigotes
98 promising compounds
99 pterocarpanquinone
100 questions
101 relevant form
102 ring
103 ring B
104 second generation
105 selective index
106 species
107 spectra
108 stress
109 structure
110 susceptibility
111 synthesis
112 tegumentary leishmaniasis
113 territory
114 therapy
115 toxicity
116 variation
117 visceral leishmaniasis
118 work
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