Probing the selective antitumor activity of 22-oxo-26-selenocyanocholestane derivatives

Fernández-Herrera, María A.; Sandoval‐Ramírez, Jesús; Sánchez-Sánchez, Luis; López-Muñoz, Hugo; Escobar-Sánchez, María L.

doi:10.1016/j.ejmech.2013.12.059

Cited by 54 publications

(14 citation statements)

References 26 publications

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“…Nevertheless, despite the design of very efficient potent anti-cancer agents, very few in vivo studies have been conducted on cold Re organometallic complexes. On the other hand, it is noteworthy that some Se-based drugs have demonstrated a selective cytotoxicity against cancerous cells [ 4 – 6 ]. The tumor-specific cytotoxic effects of Se, with special emphasis on cascades of cellular events induced by pharmacologically active Se compounds have been recently reviewed [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

Antitumor activity of a rhenium (I)-diselenoether complex in experimental models of human breast cancer

Collery¹,

Mohsen

Kermagoret

et al. 2015

Invest New Drugs

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SummaryRhenium (I)-diselenother (Re-diselenoether) is a water soluble metal-based compound, combining one atom of rhenium and two atoms of selenium. This compound has been reported to exhibit marked activities against several solid tumor cell lines. We now disclose an improved synthesis of this complex. The Re-diselenoether showed a potent inhibitory effect on MDA-MB231 cell division in vitro, which lasted when the complex was no longer present in the culture. Re-diselenoether induced a remarkable reduction of the volume of the primitive breast tumors and of the pulmonary metastases without clinical signs of toxicity, in mice-bearing a MDA-MB231 Luc+ tumor, orthotopically transplanted, after a daily oral administration at the dose of 10 mg/kg/d. Interestingly, an antagonism was observed when cisplatin was administered as a single i.p. injection 1 week after the end of the Re-diselenoether administration. In an effort to gain insight of the mechanisms of action of Re-diselenoether complex, interaction with 9-methylguanine as a nucleic acid base model was studied. We have shown that Re-diselenoether gave both mono- and bis-guanine Re adducts, the species assumed to be responsible for the DNA intrastrand lesions.Electronic supplementary materialThe online version of this article (doi:10.1007/s10637-015-0265-z) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

Antitumor activity of a rhenium (I)-diselenoether complex in experimental models of human breast cancer

Collery¹,

Mohsen

Kermagoret

et al. 2015

Invest New Drugs

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“…Several reports have shown vast and miscellaneous types of structures applying this approach, resulting in very promising antitumoral compounds in preclinical models (12,13). Recently, our research group has been using this rational design in order to obtain new derivatives with potent and selective antileishmanicidal activity.…”

mentioning

confidence: 99%

Novel Heteroaryl Selenocyanates and Diselenides as Potent Antileishmanial Agents

Baquedano

Alcolea

Toro

et al. 2016

Antimicrob Agents Chemother

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A series of new selenocyanates and diselenides bearing interesting bioactive scaffolds (quinoline, quinoxaline, acridine, chromene, furane, isosazole, etc.) was synthesized, and their in vitro leishmanicidal activities against Leishmania infantum amastigotes along with their cytotoxicities in human THP-1 cells were determined. Interestingly, most tested compounds were active in the low micromolar range and led us to identify four lead compounds (1h, 2d, 2e, and 2f) with 50% effective dose (ED 50 ) values ranging from 0.45 to 1.27 M and selectivity indexes of >25 for all of them, much higher than those observed for the reference drugs. These active derivatives were evaluated against infected macrophages, and in order to gain preliminary knowledge about their possible mechanism of action, the inhibition of trypanothione reductase (TryR) was measured. Among these novel structures, compounds 1h (3,5-dimethyl-4-isoxazolyl selenocyanate) and 2d [3,3=-(diselenodiyldimethanediyl)bis(2-bromothiophene)] exhibited good association between TryR inhibitory activity and antileishmanial potency, pointing to 1h, for its excellent theoretical ADME (absorption, distribution, metabolism, and excretion) properties, as the most promising lead molecule for leishmancidal drug design.

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“…The toxic activity shown by saponins has allowed them to be considered as possible therapeutic agents, but it is important to contemplate the possible side effects caused by their toxicity, since drugs have a dual effect; i.e., while they control certain pathologies and contribute to curing particular diseases, they can have harmful side effects that cause adverse consequences and symptoms in the body. Recent reports suggest that some saponins exhibit antiproliferative and apoptotic activity and act selectively without presenting cytotoxicity [28][29][30][31][32]. These findings are generating great interest in these compounds as therapeutic agents for treating cancer.…”

Section: Steroidal Saponins Derive From Diverse Plant Sourcesmentioning

confidence: 99%

Steroidal Saponins and Cell Death in Cancer

Escobar-Sánchez¹,

Sánchez-Sánchez²,

JesúsSandoval-Ramírez³

2015

Cell Death - Autophagy, Apoptosis and Necrosis

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Steroidal saponins are natural glycosidic compounds of amphiphilic character. Their diverse biological activities are directly related to the variability of their structural constitutive frameworks, aglycones, and sugars. Several studies have demonstrated the therapeutic potential of steroidal saponins by their capacity to induce programmed cell death in different tumor cell lines. The process of cell death is required to maintain cellular and tissular homeostasis it has been established that disturbances in the balance between cellular proliferation and cell death lead to several pathologies, including cancer. The antitumor activity of steroidal saponins has been intensely studied allowing elucidation of their different molecular mechanisms of action this knowledge is crucial to the establishment of new therapeutic strategies against cancer.

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Probing the selective antitumor activity of 22-oxo-26-selenocyanocholestane derivatives

Cited by 54 publications

References 26 publications

Antitumor activity of a rhenium (I)-diselenoether complex in experimental models of human breast cancer

Antitumor activity of a rhenium (I)-diselenoether complex in experimental models of human breast cancer

Novel Heteroaryl Selenocyanates and Diselenides as Potent Antileishmanial Agents

Steroidal Saponins and Cell Death in Cancer

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