A new article just come out!

Catalysis-free synthesis of thiazolidine–thiourea ligands for metal coordination (Au and Ag) and preliminary cytotoxic studies, Salvador-Gil, D.; Herrera, R. P.; Gimeno, M. C.  Dalton Trans. 2023. DOI: https://doi.org/10.1039/D3DT00079F.

Abstract. The reaction of propargylamines with isothiocyanates results in the selective formation of iminothiazolidines, aminothiazolines or mixed thiazolidine–thiourea compounds under mild conditions. It has been observed that secondary propargylamines lead to the selective formation of cyclic 2-amino-2-thiazoline derivatives, while primary propargylamines form iminothiazoline species. In addition, these cyclic thiazoline derivatives can further react with an excess of isothiocyanate to give rise to thiazolidine–thiourea compounds. These species can also be achieved by reaction of propargylamines with isothiocynates in a molar ratio of 1 : 2. Coordination studies of these heterocyclic species towards silver and gold with different stoichiometries have been carried out and complexes of the type [ML(PPh3)]OTf, [ML2]OTf (M = Ag, Au) or [Au(C6F5)L] have been synthesised. Preliminary studies of the cytotoxic activity in lung cancer cells have also been performed in both ligands and complexes, showing that although the ligands do not exhibit anticancer activity, their coordination to metals, especially silver, greatly enhances the cytotoxic activity.

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Help us spread the Fanny’s 3Min video

We are participating in the IV edition of the scientific dissemination contest of CSIC “Yo investigo. Yo soy CSIC” with the Fanny’s video in 3 minutes.

If you like the video, please give us a like in youtube! Thank you!

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Jandro, the new PhD student

Jandro has been recently arrived to Zaragoza from Galicia full of hope. He expleined to us his interesting previous research during his Bachelor and Master Theses.

He is already an HOCA member 😉 Welcome and good luck!

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Sara working for his Bachelor thesis

Cheer up Sara, you can!

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Happy birthday Christian!

We all wish you all the best 😉

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Sandra on the radio

Sandra had a good time last January 31st talking about Science and SDGs on the radio onda aragonesa, #FuturoConCiencia (A TU BOLA, from min 00:28:00 to min 1:02:20).

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Juan, goodbye and good luck in the future!

Juan, thank you for being with us for almost two years. It has been a pleasure to share so many things with you during this short but intense period of time.

We hope you never lose your special and lovely sense of humor;-)

Don’t forget us, we won’t forget you for sure!!

Visit us whenever you want, this is your home 😉

We wish you all the best! Thousands of kisses!

Juan opening a present for his departure.
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Merry christmas and happy new year 2023!

We, all together, celebrate the coming Christmas time and New Year! Nice dinner with nice people!! What else??

Roberto, Javi, Marta, Juan Carlos, Eva, Elisa, Sandra, Irati, Christian, Guillermo, Adrián, Noelia and Fanny.
Eduardo, Goyo, Jorge, Juan, Vanesa, Maru, Elena, Conchita, Raquel and Javier.
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The young chemists and physicists of Aragon told us about their work

The 10th Young Aragonese Researchers Meeting took place last December 14th) in the Faculty of Sciences (Zaragoza). 10ª Jornada de Jóvenes Investigadores (Química y Física) de Aragón. (10ª JJIQFA)

Guillermo, Sandra, Fanny, Christian and Juan Carlos successfully presented part of their Doctoral Thesis work. Juan Carlos received a best poster award, congratulations!

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New work on DHPs, just available online!

Congratulations to everyone, in special to Sandra! Well done!

1-Benzamido-1,4-dihydropyridine derivatives as anticancer agents: in vitro and in vivo assays, Ardevines, S.; Auria-Luna, F.; Romanos, E.; Fernández-Moreira, V.; Benedi, A.; Gimeno, M. C.; Marzo, I.; Marqués-López, E.; Herrera, R. P. Arab. J. Chem. 2022, 104514. https://doi.org/10.1016/j.arabjc.2022.104514.

Abstract. 1,4-Dihydropyridine is a privileged scaffold present in many bioactive molecules, from coenzymes to commercially available drugs. Among other interesting properties, it has been found good anticancer activity in some of these 1,4-DHPs, therefore many research groups are trying to develop new compounds based on this structural core.

For this purpose, in this work, a new family of 23 1,4-dihydropyridines has been synthesized using hydrazide and malononitrile derivatives as precursors. This straightforward catalytic process has given rise to the desired products with moderate to excellent yields. All the compounds have been tested against four different cancer cell lines [HeLa (human cervical carcinoma), Jurkat (leukemia), A549 (human lung cancer) and MIA PaCa-2 (pancreatic cancer)] to establish a preliminary structure-activity relationship. From this study, and among the best candidates, we chose 4-chlorophenyl and 4-thifluoromethylphenyl derivatives in the malononitrile ring to synthesize a second generation of molecules with enhanced cytotoxicity, modifying the substituent in the N-heterocyclic position (acylhydrazine moieties). With this second generation of compounds, we successfully decreased the IC50 until 7 µM.

An in-depth analysis of their biological properties suggests that these promising compounds trigger a non-conventional cell death mechanism known as paraptosis. Moreover, the tested photophysical properties of these products show in some cases an interesting long wavelength emission and excitation, potentially leading to new biosensors or theragnostic agents.

Finally, in vivo assays concerning the acute toxicity in mice of two of the most active compounds (with an alkyl chain of seven carbon atoms in the acylhydrazine moiety) demonstrated that even dosed at thousands fold the corresponding IC50 values (2500 and 3300 times more concentrated than the IC50 values for the two compounds studied), there was no sign of harmful effects to the tested subjects, results that support their use in further studies to discover new anticancer drugs.

Keywords. cancer; hydrazide; 1,4-dihydropyridine; in vitro; in vivo (mice); paraptosis; theranostic

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