Caesalpinioflavone, a New Cytotoxic Biflavonoid Isolated from<i>Caesalpinia pluviosa</i>var.<i>peltophoroides</i>

Zanin, João L. B.; Massoni, Murilo; Santos, Marcelo Henrique dos; Freitas, Giovana C; Niero, Evandro L. O.; Schefer, Renata Rabelo; Lago, João Henrique G.; Ionta, Marisa; Soares, Marisi G.

doi:10.5935/0103-5053.20150043

Cited by 7 publications

(6 citation statements)

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“…Cell Cycle Analysis. Cell cycle analysis was performed according to Zanin et al (2015). 65 Briefly, the cells were treated with compounds 3c and 3g at concentrations of 5 or 10 μM for 24 and 48 h. The cells were fixed in 75% methanol overnight at 4 °C.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Design, Synthesis, and Pharmacological Evaluation of NovelN-Acylhydrazone Derivatives as Potent Histone Deacetylase 6/8 Dual Inhibitors

Rodrigues¹,

Ferreira-Silva

Ferreira

et al. 2016

J. Med. Chem.

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This manuscript describes a novel class of N-acylhydrazone (NAH) derivatives that act as histone deacetylase (HDAC) 6/8 dual inhibitors and were designed from the structure of trichostatin A (1). Para-substituted phenyl-hydroxamic acids presented a more potent inhibition of HDAC6/8 than their meta analogs. In addition, the effect of compounds (E)-4-((2-(4-(dimethylamino)benzoyl)hydrazono)methyl)-N-hydroxybenzamide (3c) and (E)-4-((2-(4-(dimethylamino)benzoyl)-2-methylhydrazono)methyl)-N-hydroxybenzamide (3f) on the acetylation of α-tubulin revealed an increased level of acetylation. These two compounds also affected cell migration, indicating their inhibition of HDAC6. An analysis of the antiproliferative activity of these compounds, which presented the most potent activity, showed that compound 3c induced cell cycle arrest and 3g induced apoptosis through caspase 3/7 activation. These results suggest HDAC6/8 as a potential target of future molecular therapies for cancer.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Design, Synthesis, and Pharmacological Evaluation of NovelN-Acylhydrazone Derivatives as Potent Histone Deacetylase 6/8 Dual Inhibitors

Rodrigues¹,

Ferreira-Silva

Ferreira

et al. 2016

J. Med. Chem.

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“…This could also occur between the rings A-C, B-B, C-B, among other possibilities that are enlarged by functional groups as OH, MeO, C═O, C═C. The occurrence of common biflavonoids in the genus Caesalpinia is known only to some species, such as C. ferrea [33], C. pyramidalis [34], C. pluviosa [35].…”

Section: Sppmentioning

confidence: 99%

Homoisoflavonoids from Caesalpinia spp.: A Closer Look at Chemical and Biological Aspects

Baldim¹,

Rosa²,

Santos³

et al. 2017

Flavonoids - From Biosynthesis to Human Health

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Homoisoflavonoids are rare compounds distributed within a few families of plants including species from Fabaceae. The genus Caesalpinia, the main focus of this chapter, is a prolific source of these unique natural products. Homoisoflavonoids from Caesalpinia spp. are associated to ethnopharmacological uses for diverse purposes. In this sense, the following chapter sheds light on the occurrence, biosynthesis, isolation, synthesis, and structural analysis of these compounds from species of the genus Caesalpinia and their biological potential.

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“…Additionally, flavonoids are also considered safe compounds with low potential to induce organic toxicity [ 17 ]. Conversely, they can exhibit prooxidant activity, explaining the mutagenic [ 14 ], cytotoxic [ 18 ], and toxic effect against parasites [ 19 , 20 ]. Prooxidant and antioxidant properties of flavonoids depend on the environment in which they are inserted and their chemical structure and concentration [ 11 , 13 ].…”

Section: Introductionmentioning

confidence: 99%

The Correlation between Chemical Structures and Antioxidant, Prooxidant, and Antitrypanosomatid Properties of Flavonoids

Baldim

Alcântara

Domingos

et al. 2017

Oxidative Medicine and Cellular Longevity

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Flavonoids have demonstrated in vivo and in vitro leishmanicidal, trypanocidal, antioxidant, and prooxidant properties. The chemotherapy of trypanosomiasis and leishmaniasis lacks efficacy, presents high toxicity, and is related to the development of drug resistance. Thus, a series of 40 flavonoids were investigated with the purpose of correlating these properties via structure and activity analyses based on integrated networks and QSAR models. The classical groups for the antioxidant activity of flavonoids were combined in order to explain the influence of antioxidant and prooxidant activities on the antiparasitic properties. These analyses become useful for the development of efficient treatments for leishmaniasis and trypanosomiasis. Finally, the dual activity of flavonoids presenting both anti- and prooxidant activities revealed that the existence of a balance between these two features could be important to the development of adequate therapeutic strategies.

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Caesalpinioflavone, a New Cytotoxic Biflavonoid Isolated fromCaesalpinia pluviosavar.peltophoroides

Cited by 7 publications

References 0 publications

Design, Synthesis, and Pharmacological Evaluation of NovelN-Acylhydrazone Derivatives as Potent Histone Deacetylase 6/8 Dual Inhibitors

Design, Synthesis, and Pharmacological Evaluation of NovelN-Acylhydrazone Derivatives as Potent Histone Deacetylase 6/8 Dual Inhibitors

Homoisoflavonoids from Caesalpinia spp.: A Closer Look at Chemical and Biological Aspects

The Correlation between Chemical Structures and Antioxidant, Prooxidant, and Antitrypanosomatid Properties of Flavonoids

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