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Second-generation pterocarpanquinones: synthesis and antileishmanial activity.

Viviane Dos Santos Faiões1, Lívia C R M da Frota2, Edézio Ferreira Cunha-Junior1

  • 11Laboratório de Bioquímica de Tripanosomatídeos, Instituto Oswaldo Cruz, FIOCUZ, Av. Brasil, 4365, Pavilhao Leonidas Deane, sala 405A, Manguinhos, Rio de Janeiro, RJ 21040-900 Brazil.

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Second-generation pterocarpanoquinones show promise as novel leishmanicidal agents. Modifications to their structure, including ring configuration and oxygenation, enhanced activity against Leishmania parasites, particularly Leishmania amazonensis.

Keywords:
Drug discoveryLQ-118LeishmaniaLeishmaniasisNeglected diseasesPhenotypic assayPterocarpanquinone

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Area of Science:

  • Medicinal Chemistry
  • Parasitology
  • Drug Discovery

Background:

  • Leishmaniasis remains a significant global health concern, with numerous countries endemic for both Tegumentary and Visceral forms.
  • Existing therapies necessitate the continuous identification of novel antileishmanial drug candidates to replenish the drug discovery pipeline.
  • First-generation pterocarpanquinones demonstrated efficacy and safety against experimental leishmaniasis, prompting further investigation into related compounds.

Purpose of the Study:

  • To synthesize and evaluate the antileishmanial activity of a second generation of pterocarpanoquinones.
  • To explore the structure-activity relationships of pterocarpanoquinones against various Leishmania species.
  • To assess the toxicity and oxidative stress-inducing potential of these novel compounds.

Main Methods:

  • Second-generation pterocarpanoquinones (2a-f) were synthesized via palladium-catalyzed oxyarylation.
  • Antileishmanial activity was assessed against promastigotes and intracellular amastigotes of *L. amazonensis*, *L. braziliensis*, and *L. infantum*.
  • Toxicity was evaluated in peritoneal macrophages, and oxidative stress markers (ROS, mitochondrial membrane potential) were measured.

Main Results:

  • Structural modifications, including ring B/C exchange and oxygenation at ring B, improved antileishmanial activity against specific Leishmania species and parasite stages.
  • The oxygenated compound 2b showed enhanced activity against *L. braziliensis* promastigotes compared to its deoxy derivative 2a.
  • Species-specific susceptibility was observed, with *L. amazonensis* being most susceptible and *L. infantum* showing resistance to most derivatives; compounds 2b and 2c induced increased ROS production.

Conclusions:

  • The synthesized pterocarpanoquinones represent a promising class of compounds for the development of new leishmanicidal agents.
  • Structural optimization of pterocarpanoquinones can lead to improved efficacy against Leishmania parasites.
  • Further investigation into the mechanism of action, including ROS induction, is warranted.