Novel gold(I) complexes with 5-phenyl-1,3,4-oxadiazole-2-thione and phosphine as potential anticancer and antileishmanial agents

Chaves, Joana Darc S.; Tunes, Lilian Vanussa Madruga de; Franco, Chris H. J.; Francisco, Thiago Martins; Corrêa, Charlane C.; Murta, Silvane Maria Fonseca; Monte-Neto, Rubens L.; Silva, Heveline; Fontes, Ana Paula Soares; Almeida, Mauro Vieira de

doi:10.1016/j.ejmech.2016.10.052

Cited by 55 publications

(27 citation statements)

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“…It has been shown that infected-BMDM treated with meglumine antimoniate for 6 days, inhibits 50 % of the amastigotes load between 39 and 196 μM for L. braziliensis, and between 296 and 407 μM for L. amazonensis in different field isolates. [33] Our data show that 3, 6 and 7 are markedly more active at lower concentrations, similarly to previously tested Au I complexes, [18,21,22] and do not require prolonged incubation times, suggesting a more immediate effect on the parasites, without affecting the host cell ( Figure 2B).…”

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confidence: 82%

“…[20] Recently, Monte-Neto and co-workers reported on the effects on promastigote and amastigote proliferation from L. infantum and L. braziliensis of a series of Au I phosphane complexes with thiol-containing ligands. [21,22] Moreover, some of the reported derivatives were effective for experimental cutaneous leishmaniasis in animal models. [22] The mode of action of these compounds involves oxidative damage through TR inhibition and mitochondrial damage.…”

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confidence: 99%

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Comparing the Antileishmanial Activity of Gold(I) and Gold(III) Compounds in L. amazonensis and L. braziliensis in Vitro

et al. 2020

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A series of mononuclear coordination or organometallic Au I /Au III complexes (1-9) have been comparatively studied in vitro for their antileishmanial activity against promastigotes and amastigotes, the clinically relevant parasite form, of Leishmania amazonensis and Leishmania braziliensis. One of the cationic Au I bis-N-heterocyclic carbenes (3) has low EC 50 values (ca. 4 μM) in promastigotes cells and no toxicity in host macrophages. Together with two other Au III complexes (6 and 7), the compound is also extremely effective in intracellular amastigotes from L. amazonensis. Initial mechanistic studies include an evaluation of the gold complexes' effect on L. amazonensis' plasma membrane integrity. Leishmaniasis is a vector-borne disease caused by Leishmania protozoan parasites that leads to cutaneous (localized, mucosal, diffuse, disseminated) or visceral manifestations, depending on the species, immune status of the host and geographic distribution. [1] Leishmania amazonensis and Leishmania braziliensis are important species related to cutaneous leishmaniasis in the New World, especially in Brazil, where about 73k to 120k people are infected every year. [2] While vaccines for humans are not available, antimony-based compounds, such as sodium stibogluconate (Pentostam®, Figure 1), amphotericin B (AMB), paromomycin, miltefosine, and pentamidine have been used for treating patients for several decades, despite their severe side effects and long-term parenteral administration in the majority of the cases. [3] In this context, a key area in [a

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confidence: 82%

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confidence: 99%

Comparing the Antileishmanial Activity of Gold(I) and Gold(III) Compounds in L. amazonensis and L. braziliensis in Vitro

et al. 2020

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“…infantum with an IC50 value of 0.97 µM 67 . Similarly, Taha and coworkers synthesized phenyl linked oxadiazole moieties which showed antileishmanial activities with compound (107) being the most prominent, with IC50 of 0.95 µM being 7 times more potent than the Pentamidine standard 121 .…”

Section: Antileishmanial Activitymentioning

confidence: 99%

Recent advances on oxadiazole motifs: Synthesis, reactions and biological activities

Ajani

Iyaye

2020

Mediterr.J.Chem.,

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<p>1,3,4-oxadiazole derivatives have shown to have diverse and vast applications, from medicinal chemistry for the treatment and possible treatment of various ailments to its application in the industrial development when used as corrosion inhibitions and light emitting diodes. These diverse applications can be as a result of the numerous viable synthetic pathways illustrated in this review. 1,3,4-oxadiazoles can be synthesized in very high yields, using green approaches and having various life-changing applications. This review explores the various recent synthetic routes available for the development of 1,3,4-oxadiazoles and their biological activities.</p>

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“…Further, a carbonyl group with a hydrazide moiety can be used instead of the oxadiazole ring. 10 The 1,3,4-oxadiazole ring is a useful heterocyclic moiety in medicinal chemistry and substituted 1,3,4-oxadiazole ring compounds exhibit different biological activities such as antibacterial, 11 herbicidal, 12 insecticidal, 13 antiviral, 14 antitumoral 15 and anti-inflammatory activities. 16 In addition to a broad spectrum of biological activities, 1,3,4-oxadiazole rings are bioisosteres of amide and ester functional groups, and it is reported that these rings can easily participate in hydrogen-bonding interactions with various different receptors.…”

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confidence: 99%

Synthesis and structure–activity relationships of carbohydrazides and 1,3,4‐oxadiazole derivatives bearing an imidazolidine moiety against the yellow fever and dengue vector, Aedes aegypti

Tok

Koçyığıt‐Kaymakcioğlu

Tabanca

et al. 2017

Pest Management Science

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Novel gold(I) complexes with 5-phenyl-1,3,4-oxadiazole-2-thione and phosphine as potential anticancer and antileishmanial agents

Cited by 55 publications

References 74 publications

Comparing the Antileishmanial Activity of Gold(I) and Gold(III) Compounds in L. amazonensis and L. braziliensis in Vitro

Comparing the Antileishmanial Activity of Gold(I) and Gold(III) Compounds in L. amazonensis and L. braziliensis in Vitro

Recent advances on oxadiazole motifs: Synthesis, reactions and biological activities

Synthesis and structure–activity relationships of carbohydrazides and 1,3,4‐oxadiazole derivatives bearing an imidazolidine moiety against the yellow fever and dengue vector, Aedes aegypti

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