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Gutierrez et al. J Org Chem. 2018;83(12):6623-6632. gamma-Carboline Synthesis by Heterocyclization of TosMIC Derivatives.
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Publicaciones > Gutierrez et al
gamma-Carboline Synthesis by Heterocyclization of TosMIC Derivatives.
Departamento de Quimica Organica y Quimica Inorganica and Instituto de Investigacion Quimica "Andres M. del Rio" (IQAR) , Universidad de Alcala , 28805 - Alcala de Henares , Madrid , Spain.
Abstract
A new method for the synthesis of gamma-carbolines by a heterocyclization that involves alpha-indol-2-ylmethyl TosMIC derivatives and different electrophiles has been developed. This methodology has been successfully applied to the synthesis of several highly substituted gamma-carbolines.
Malvicini et al. Mol Cancer Ther. 2018;17(5):966-976. A Tricin Derivative from Deschampsia antarctica Desv. Inhibits Colorectal Carcinoma Growth and Liver Metastasis through the Induction of a Specific Immune Response.
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Publicaciones > Malvicini et al
A Tricin Derivative from Deschampsia antarctica Desv. Inhibits Colorectal Carcinoma Growth and Liver Metastasis through the Induction of a Specific Immune Response.
1. Gene Therapy Laboratory, Instituto de Investigaciones en Medicina Traslacional, Facultad de Ciencias Biomedicas, CONICET- Universidad Austral, Buenos Aires, Argentina. 2. Universidad Autonoma de Chile, Providencia, Chile. 3. Universidad de La Frontera, Temuco, Chile. 4. Departamento de Quimica Organica, Universidad de Alcala, Madrid, Spain. 5. Beth Israel Deaconess Medical Center, Harvard Medical School, Boston, Massachusetts. 6. Gastrointestinal Cancer Clinical Research Unit, CNIO - Spanish National Cancer Research Center, Madrid, Spain. 7. Creative BioScience, Huechuraba, Santiago, Chile.
a. gmazzoli@cas.austral.edu.ar, mgidekel@creativebio-science.com
Abstract
In colorectal carcinoma patients, distant metastatic disease is present at initial diagnosis in nearly 25% of them. The majority of patients with metastatic colorectal carcinoma have incurable disease; therefore, new therapies are needed. Agents derived from medicinal plants have already demonstrated therapeutic activities in human cancer cells. Antartina is an antitumor agent isolated from Deschampsia antarctica Desv. This study aimed to evaluate the antitumor properties of Antartina in colorectal carcinoma models. We used human and murine colorectal carcinoma cell lines for investigating proliferation, apoptosis, and cell-cycle effects of Antartina therapy in vitro Avatar and immunocompetent colorectal carcinoma animal models were applied for evaluating the effects of Antartina in vivo Immune response against colorectal carcinoma model was investigated using CTL assay, analyzing dendritic cell activation and intratumor T-cell subpopulation, and by tumor rechallenge experiments. Antartina inhibits in vitro human colorectal carcinoma cell proliferation; however, in vivo experiments in Avatar colorectal carcinoma model Antartina display a limited antitumor effect. In an immunocompetent colorectal carcinoma mice model, Antartina potently inhibited tumor growth and liver metastases, leading to complete tumor regressions in >30% of mice and increased animal survival. In addition, Antartina induced a potent specific cytotoxic T-cell response against colorectal carcinoma and a long-lasting antitumor immunity. Interestingly, Antartina increased tumor immunogenicity and stimulated dendritic cell activation. No toxic effects were observed at the doses employed. Our findings showed that Antartina has the ability to induce antitumor immunity against colorectal carcinoma and can be used to develop new tools for the treatment of colorectal carcinoma. Mol Cancer Ther; 17(5); 966-76. (c)2018 AACR.
Abengozar et al. Chem Commun (Camb). 2018;54(20):2467-2470. Synthesis of functionalized helical BN-benzo[c]phenanthrenes.
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Publicaciones > Abengozar et al
Synthesis of functionalized helical BN-benzo[c]phenanthrenes.
Departamento de Quimica Organica y Quimica Inorganica, Instituto de Investigacion Quimica "Andres M. del Rio" (IQAR), Universidad de Alcala, 28805-Alcala de Henares, Madrid, Spain.
a. patricia.garciagarci@uah.es, juanjose.vaquero@uah.es
Abstract
A novel parent BN-benzo[c]phenanthrene, with helical chirality and remarkable structural features, has been easily obtained in three steps with a global yield of 55%. Moreover, Cl-substituted derivatives have been prepared and these have served as useful starting materials for the development of palladium-catalyzed cross-coupling reactions.
Abengozar et al. Org Lett. 2017;19(13):3458-3461. Synthesis, Optical Properties, and Regioselective Functionalization of 4a-Aza-10a-boraphenanthrene.
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Publicaciones > Abengozar et al
Synthesis, Optical Properties, and Regioselective Functionalization of 4a-Aza-10a-boraphenanthrene.
1. Departamento de Quimica Organica y Quimica Inorganica, Universidad de Alcala , 28871 Alcala de Henares, Madrid, Spain. 2. Departamento de Quimica Analitica, Quimica Fisica e Ingenieria Quimica, Universidad de Alcala , 28871 Alcala de Henares, Madrid, Spain. 3. Departamento de Quimica, Centro de Investigacion en Sintesis Quimica (CISQ), Universidad de La Rioja , Madre de Dios 53, 26006 Logrono, Spain.
Abstract
4a-Aza-10a-boraphenanthrene has been synthesized in only four steps from commercially available materials with a remarkable overall yield of 62%. In contrast to other BN-isosteres of phenathrene, this isomer is weakly fluorescent, which has been explained by means of computational studies that found a low energy conical intersection for the nonradiative deactivation of the excited state. Moreover, a completely regioselective functionalization of 4a-aza-10a-boraphenanthrene at C-1 by reaction with activated electrophiles has been achieved.
Vasilev et al. Beilstein J Org Chem. 2017;13:2902-2914. Halogen-containing thiazole orange analogues – new fluorogenic DNA stains.
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Halogen-containing thiazole orange analogues - new fluorogenic DNA stains.
1. Department of Pharmaceutical and Applied Organic Chemistry, Faculty of Chemistry and Pharmacy, Sofia University "St. Kliment Ohridski", 1 James Bourchier Blvd., 1164 Sofia, Bulgaria. 2. Department of Organic Chemistry and Pharmacognosy, Faculty of Chemistry and Pharmacy, Sofia University "St. Kliment Ohridski", 1 James Bourchier Blvd., 1164 Sofia, Bulgaria. 3. Departments of Organic and Physical Chemistry, University of Alcala, 28871-Alcala de Henares, Madrid, Spain. 4. Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany.
Keywords: DFT calculations; cyanine dyes; green synthesis; nucleic acids; thiazole orange
Abstract
Novel asymmetric monomeric monomethine cyanine dyes 5a-d, which are analogues of the commercial dsDNA fluorescence binder thiazole orange (TO), have been synthesized. The synthesis was achieved by using a simple, efficient and environmetally benign synthetic procedure to obtain these cationic dyes in good to excellent yields. Interactions of the new derivatives of TO with dsDNA have been investigated by absorption and fluorescence spectroscopy. The longest wavelength absorption bands in the UV-vis spectra of the target compounds are in the range of 509-519 nm and these are characterized by high molar absorptivities (63000-91480 L.mol(-1).cm(-1)). All investigated dyes from the series are either not fluorescent or their fluorescence is quite low, but they become strongly fluorescent after binding to dsDNA. The influence of the substituents attached to the chromophores was investigated by combination of spectroscopic (UV-vis and fluorescence spectroscopy) and theoretical (DFT and TDDFT calculations) methods.
Sucunza et al. J Org Chem. 2016;81(21):10126-10135. Recent Advances in the Synthesis of Azonia Aromatic Heterocycles.
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Recent Advances in the Synthesis of Azonia Aromatic Heterocycles.
Department of Organic and Inorganic Chemistry, University of Alcala , 28871 Alcala de Henares, Madrid, Spain.
Abstract
Azonia aromatic heterocycles are an important subclass of aza-heterocyles as they are the structural motif of relevant cationic alkaloids, and they have a wide range of potential applications such as bioactive compounds and organic materials. In this Synopsis, recent and novel approaches to their synthesis are surveyed, with particular emphasis on ring-closing metathesis reactions and annulation reactions based on C-H activation.
Gutierrez et al. Org Lett. 2016;18(14):3378-81. Synthesis of 1-Substituted Isoquinolines by Heterocyclization of TosMIC Derivatives: Total Synthesis of Cassiarin A.
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Publicaciones > Gutierrez et al
Synthesis of 1-Substituted Isoquinolines by Heterocyclization of TosMIC Derivatives: Total Synthesis of Cassiarin A.
Departamento de Quimica Organica y Quimica Inorganica, Universidad de Alcala , Alcala de Henares 28871, Spain.
Abstract
A new method for the synthesis of 1-substituted isoquinolines by a heterocyclization that involves alpha-benzyl TosMIC derivatives and different electrophiles has been developed. This methodology has been successfully applied to a total synthesis of cassiarin A, an alkaloid with potent antiplasmodial activity against Plasmodium falciparum.
Gutierrez et al. Chemistry. 2015;21(51):18758-63. Highly Fluorescent Green Fluorescent Protein Chromophore Analogues Made by Decorating the Imidazolone Ring.
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Publicaciones > Gutierrez et al
Highly Fluorescent Green Fluorescent Protein Chromophore Analogues Made by Decorating the Imidazolone Ring.
1. Departamento de Quimica Organica y Quimica Inorganica, Universidad de Alcala, Edificio de Farmacia, 28871, Alcala de Henares, Madrid (Spain). 2. Departamento de Quimica, Centro de Investigacion en Sintesis Quimica (CISQ), Universidad de La Rioja, Madre de Dios, 53, 26006, Logrono, La Rioja (Spain). 3. Departamento de Biologia de Sistemas, Universidad de Alcala, Edificio de Medicina, 28871, Alcala de Henares, Madrid (Spain). 4. Departamento de Quimica, Universidad Yachay Tech, Hacienda San Jose s/n, San Miguel de Urcuqui, 100119 (Ecuador).
a. david.sucunza@uah.es a. diego.sampedro@unirioja.es a. juanjose.vaquero@uah.es
Keywords: TD-DFT calculations; cell staining; fluorescence; imidazolone derivatives; proteins
Abstract
The synthesis and photophysical behavior of an unexplored family of green fluorescent protein (GFP)-like chromophore analogues is reported. The compound (Z)-4-(4-hydroxybenzylidene)-1-propyl-2-(propylamino)-1H-imidazol-5(4 H)-one (p-HBDNI, 2 a) exhibits significantly enhanced fluorescence properties relative to the parent compound (Z)-5-(4-hydroxybenzylidene)-2,3-dimethyl-3,5-dihydro-4H-imidazol-4-one (p-HBDI, 1). p-HBDNI was considered as a model system and the photophysical properties of other novel 2-amino-3,5-dihydro-4H-imidazol-4-one derivatives were evaluated. Time-dependent DFT calculations were carried out to rationalize the results. The analogue AIDNI (2 c), in which the 4-hydroxybenzyl group of p-HBDNI was replaced by an azaindole group, showed improved photophysical properties and potential for cell staining. The uptake and intracellular distribution of 2 c in living cells was investigated by confocal microscopy imaging.
Suarez et al. Org Biomol Chem. 2015;13(2):527-38. Targeting DNA with small molecules: a comparative study of a library of azonia aromatic chromophores.
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Targeting DNA with small molecules: a comparative study of a library of azonia aromatic chromophores.
Departamento de Quimica Organica y Quimica Inorganica, Universidad de Alcala, 28871-Alcala de Henares, Madrid, Spain.
a. juanjose.vaquero@uah.es
Abstract
A library of azonia aromatic cations has been studied in order to gain insights into the effect of the size, shape and charge distribution on the fluorescence, DNA interactions and DNA sequence selectivity properties. Fluorescence-based thermal denaturation experiments, spectrofluorimetric titrations, circular dichroism measurements and theoretical simulations have shown that some of the studied chromophores have interesting fluorescence properties and two of them also show a consistent DNA-binding ability by intercalation, with a potential preference for AT-rich sequences.