scholarly journals New Developments in the Synthesis of EMICORON

2018 ◽  
Author(s):  
Marco Franceschin ◽  
Ilaria Serafini ◽  
Alessandro Ciccòla ◽  
Claudio Frezza ◽  
Armandodoriano Bianco ◽  
...  
Keyword(s):  
Mechanism Of Action ◽  
Growth And Development ◽  
Reaction Times ◽  
Preclinical Studies ◽  
Antitumor Activities ◽  
Reaction Conditions ◽  
New Developments ◽  
Work Up ◽  
First Time

In this paper, the modification of two synthetic steps to obtain EMICORON, with respect to the usual protocol, is reported. EMICORON is a benzo[ghi]perylen-diimmide which was synthesized the first time in our laboratory in 2012 and showed to have in-vivo antitumor activities interfering with tumor growth and development by a multi-target mechanism of action. The provided modifications regarded the reaction times and the reaction conditions as well as the work-up procedures and allowed to increase the global yield of the process from 28% to about 40%. Thus, this new procedure may be more suitable in order to get larger amounts of EMICORON for further preclinical studies.

scholarly journals New Developments in the Synthesis of EMICORON

2018 ◽  
Vol 7 (3) ◽  
pp. 22 ◽  
Author(s):  
Massimo Pitorri ◽  
Marco Franceschin ◽  
Ilaria Serafini ◽  
Alessandro Ciccòla ◽  
Claudio Frezza ◽  
...  
Keyword(s):  
Mechanism Of Action ◽  
Growth And Development ◽  
Reaction Times ◽  
Preclinical Studies ◽  
Antitumor Activities ◽  
Reaction Conditions ◽  
New Developments ◽  
Work Up ◽  
First Time

This paper reports on the modification of two synthetic steps in the usual protocol used for obtaining EMICORON. EMICORON is a benzo[ghi]perylen-diimide, which was synthesized for the first time in our laboratory in 2012, and has shown to have in vivo antitumor activities that interferes with the tumor growth and development using a multi-target mechanism of action. The provided modifications, which involved the reaction times, the reaction conditions, and the work-up procedures, allowed the global yield of the process to be increased from 28% to about 40%. Thus, this new procedure may be more suitable for recovering higher amounts of EMICORON to be used in further preclinical studies.

scholarly journals Response of Cisplatin Resistant Skov-3 Cells to [Pt(O,O′-Acac)(γ-Acac)(DMS)] Treatment Revealed by a Metabolomic 1H-NMR Study

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2301 ◽  
Author(s):  
Federica De Castro ◽  
Michele Benedetti ◽  
Giovanna Antonaci ◽  
Laura Del Coco ◽  
Sandra De Pascali ◽  
...  
Keyword(s):  
Ovarian Carcinoma ◽  
1H Nmr ◽  
Mechanism Of Action ◽  
Culture Media ◽  
Epithelial Ovarian Carcinoma ◽  
Multivariate Statistical ◽  
Nmr Study ◽  
First Time

The novel [Pt(O,O′-acac)(γ-acac)(DMS)], Ptac2S, Pt(II) complex has recently gained increasing attention as a potential anticancer agent for its pharmacological activity shown in different tumor cell lines, studied both in vitro and in vivo. The mechanism of action of Ptac2S, operating on non-genomic targets, is known to be very different from that of cis-[PtCl2(NH3)2], cisplatin, targeting nucleic acids. In this work, we evaluated the cytotoxicity of Ptac2S on the cisplatin resistant Epithelial Ovarian Carcinoma (EOC), SKOV-3 cells, by the MTT assay. A 1H-NMR metabolomic approach coupled with multivariate statistical analysis was used for the first time for Ptac2S to figure out the biological mechanisms of action of the complex. The metabolic variations of intracellular metabolites and the composition of the corresponding extracellular culture media were compared to those of cisplatin (cells were treated at the IC50 doses of both drugs). The reported comparative metabolomic analysis revealed a very different metabolic profile between Ptac2S and cisplatin treated samples, thus confirming the different mechanism of action of Ptac2S also in the Epithelial Ovarian Carcinoma (EOC), SKOV-3 cells line. In particular, higher levels of pyruvate were observed in Ptac2S treated, with respect to cisplatin treated, cells (in both aqueous and culture media). In addition, a very different lipid expression resulted after the exposure to the two drugs (Ptac2S and cisplatin). These results suggest a possible explanation for the Ptac2S ability to circumvent cisplatin resistance in SKOV-3 cells.

Deep eutectic solvent-catalyzed Meyer–Schuster rearrangement of propargylic alcohols under mild and bench reaction conditions

2020 ◽  
Vol 56 (96) ◽  
pp. 15165-15168
Author(s):  
Nicolás Ríos-Lombardía ◽  
Luciana Cicco ◽  
Kota Yamamoto ◽  
José A. Hernández-Fernández ◽  
Francisco Morís ◽  
...  
Keyword(s):  
Room Temperature ◽  
Deep Eutectic Solvent ◽  
Reaction Times ◽  
Reaction Conditions ◽  
Propargylic Alcohols ◽  
First Time

Faster, milder, greener…better! The Meyer–Schuster rearrangement is disclosed for the first time in a deep eutectic solvent, namely FeCl3·6H2O/glycerol (3 : 1), enabling the reaction at room temperature, under air and with short reaction times.

Antitumor Activities of Extracts and Compounds from Water Decoctions of Taxus cuspidata

2010 ◽  
Vol 38 (06) ◽  
pp. 1107-1114 ◽  
Author(s):  
Shougang Jiang ◽  
Yu Zhang ◽  
Yuangang Zu ◽  
Zhuo Wang ◽  
Yujie Fu
Keyword(s):  
Antitumor Activity ◽  
Water Soluble ◽  
Taxus Cuspidata ◽  
Antitumor Activities ◽  
Antitumor Effects ◽  
Anticancer Properties ◽  
Specific Host ◽  
First Time

Water decoctions from the leaves of Taxus cuspidata are used in traditional Chinese medicine to treat cancer, suggesting that water soluble constituents from these leaves may possess anticancer properties. Interestingly, hydrophilic paclitaxel derivatives, as opposed to paclitaxel itself, can be detected by high pressure liquid chromatography in water decoctions from these leaves. The remainder extracts, which are free of paclitaxel and hydrophilic paclitaxel derivatives, from the T. cuspidata leaves were investigated for antitumor activity in vivo and in vitro for the first time in this study. EE80B, 7-xylosyl-10-deacetylpaclitaxel and 7-xylosyl-10-deacetylpaclitaxel C displayed the most antitumor activity in vivo. However, in vitro studies with tumor cell lines showed that EE80B had a significantly smaller antitumor effect than paclitaxel. We hypothesize that water decoctions from T. cuspidata leaves exhibit antitumor effects in vivo, which may be aided by the activation of specific host mechanisms (e.g. stimulation of antitumor immunity) which are not present in vitro.

scholarly journals Polystyrene-supported aluminum chloride as an efficient and reusable catalyst for condensation of indole with various carbonyl compounds

2010 ◽  
Vol 75 (4) ◽  
pp. 423-431 ◽  
Author(s):  
Bahman Tamami ◽  
Nasrolahi Shirazi ◽  
Parvanak Borujeni
Keyword(s):  
Aluminum Chloride ◽  
Carbonyl Compounds ◽  
Low Cost ◽  
Reaction Times ◽  
Reusable Catalyst ◽  
Reaction Conditions ◽  
Crosslinked Polystyrene ◽  
Aldehydes And Ketones ◽  
Polymeric Catalyst ◽  
Work Up

Crosslinked polystyrene-supported aluminum chloride (Ps-AlCl3) is a stable, recyclable and environmental friendly heterogeneous catalyst for the condensation of indole with aldehydes and ketones to afford bis-indolylmethanes. In addition, (Ps-AlCl3) shows satisfactory selectivity in the reaction of mixtures of an aldehyde and a ketone with indole. Although AlCl3 is a water sensitive, corrosive and environmentally harmful compound, Ps-AlCl3 is a stable and water-tolerant species. The mild reaction conditions, short reaction times, easy work-up, high to excellent yields, chemoselectivity, reuse of the catalyst for at least ten times without significant change in its catalytic activity, low cost, and easy preparation and handling of the polymeric catalyst are obvious advantages of the present method.

scholarly journals One-pot, three-component synthesis of pyrrolo[2,3-d]pyrimidine derivatives

2018 ◽  
Vol 62 (1) ◽  
Author(s):  
Jabbar Khalafy ◽  
Ramin Javahershenas
Keyword(s):  
Simple Procedure ◽  
Reaction Times ◽  
Pyrimidine Derivatives ◽  
Reaction Conditions ◽  
One Pot ◽  
General Applicability ◽  
Green Approach ◽  
Three Component Reaction ◽  
High Yields ◽  
Work Up

<p>A green approach for the synthesis of polyfunctionalized pyrrolo[2,3-<em>d</em>]pyrimidine derivatives was successfully achieved by a one-pot, three-component reaction of arylglyoxals, 6-amino-1,3-dimethyluracil and barbituric acid derivatives in the presence of tetra-<em>n</em>-butylammonium bromide (TBAB) (5 mol%) as the catalyst in ethanol at 50 °C. This protocol has many advantages such as high yields (73-95%), green and simple procedure, short reaction times, easy work-up, mild reaction conditions and general applicability.</p>

scholarly journals A Simple and Green Procedure for the Synthesis of 5-Arylidenerhodanines Catalyzed by Diammonium Hydrogen Phosphate in Water

2013 ◽  
Vol 2013 ◽  
pp. 1-4
Author(s):  
Liangliang Han ◽  
Tao Wu ◽  
Zhongqiang Zhou
Keyword(s):  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Hydrogen Phosphate ◽  
Reaction Conditions ◽  
Efficient Procedure ◽  
Diammonium Hydrogen Phosphate ◽  
High Yields ◽  
Green Procedure ◽  
Work Up ◽  
Diammonium Hydrogen

A simple and efficient procedure for the synthesis of 5-arylidenerhodanines by condensation of aromatic aldehydes with rhodanine in water using diammonium hydrogen phosphate as catalyst is described. The procedure offers several advantages including environmentally friendly, mild reaction conditions, short reaction times, high yields, and simple experimental and work-up procedures.

scholarly journals OsIAGT1 Is a Glucosyltransferase Gene Involved in the Glucose Conjugation of Auxins in Rice

Rice ◽  
2019 ◽  
Vol 12 (1) ◽  
Author(s):  
Qian Liu ◽  
Ting-Ting Chen ◽  
Dong-Wang Xiao ◽  
Shu-Man Zhao ◽  
Ji-Shan Lin ◽  
...  
Keyword(s):  
Growth And Development ◽  
Sequence Similarity ◽  
Ectopic Expression ◽  
Reaction Conditions ◽  
Auxin Homeostasis ◽  
Auxin Synthesis ◽  
Glucose Conjugation ◽  
The One

Abstract Background In cereal crop rice, auxin is known as an important class of plant hormone that regulates a plethora of plant growth and development. Glycosylation of auxin is known to be one of the important mechanisms mediating auxin homeostasis. However, the relevant auxin glucosyltransferase (GT) in rice still remains largely unknown. Results In this study, using known auxin glucosyltransferases from other species as queries, twelve putative auxin UDP-glycosyltransferase (UGT) genes were cloned from rice and the one showing highest sequence similarity, named as OsIAGT1, was expressed as recombinant protein. In vitro enzymatic analysis showed that recombinant OsIAGT1 was capable of catalyzing glucosylation of IAA, IBA and other auxin analogs, and that OsIAGT1 is quite tolerant to a broad range of reaction conditions with peak activity at 30 °С and pH 8.0. OsIAGT1 showed favorite activity towards native auxins over artificially synthesized ones. Further study indicated that expression of OsIAGT1 can be upregulated by auxin in rice, and with OsIAGT1 overexpressing lines we confirmed that OsIAGT1 is indeed able to glucosylate IAA in vivo. Consistently, ectopic expression of OsIAGT1 leads to declined endogenous IAA content, as well as upregulated auxin synthesis genes and reduced expression of auxin-responsive genes, which likely leads to the reduced plant stature and root length in OsIAGT1 overexpression lines. Conclusion Our result indicated that OsIAGT1 plays an important role in mediating auxin homeostasis by catalyzing auxin glucosylation, and by which OsIAGT1 regulates growth and development in rice.

scholarly journals DSPE-PEG Modification of α-Conotoxin TxID

Marine Drugs ◽  
2019 ◽  
Vol 17 (6) ◽  
pp. 342 ◽  
Author(s):  
Weinan Zhao ◽  
Yang Xiong ◽  
Dongting Zhangsun ◽  
Sulan Luo
Keyword(s):  
Future Application ◽  
Dimethyl Formamide ◽  
Xenopus Laevis Oocytes ◽  
Solvent Ratio ◽  
Drug Rehabilitation ◽  
Reaction Conditions ◽  
Drug Lead ◽  
First Time

In order to improve stability of a peptide marine drug lead, α-conotoxin TxID, we synthesized and modified TxID at the N-terminal with DSPE-PEG-NHS by a nucleophilic substitution reaction to prepare the DSPE-PEG-TxID for the first time. The reaction conditions, including solvent, ratio, pH, and reaction time, were optimized systematically and the optimal one was reacted in dimethyl formamide at pH 8.2 with triethylamine at room temperature for 120 h. The in vitro stabilities in serum, simulated gastric juice, and intestinal fluid were tested, and improved dramatically compared with TxID. The PEG-modified peptide was functionally tested on α3β4 nicotinic acetylcholine receptor (nAChR) heterologously expressed in Xenopus laevis oocytes. The DSPE-PEG-TxID showed an obvious inhibition effect on α3β4 nAChR. All in all, the PEG modification of TxID was improved in stability, resistance to enzymatic degradation, and may prolong the half-life in vivo, which may pave the way for the future application in smoking cessation and drug rehabilitation, as well as small cell lung cancer.

Catalyst-Free Three-Component Synthesis of Spirobenzimidazolidines Bearing an Indole Scaffold

Synlett ◽  
2018 ◽  
Vol 29 (17) ◽  
pp. 2301-2305 ◽  
Author(s):  
F. Moghaddam ◽  
A. Moafi ◽  
Z. Zamani ◽  
M. Daneshfar
Keyword(s):  
Reaction Times ◽  
Reaction Conditions ◽  
One Pot ◽  
Efficient Catalyst ◽  
Catalyst Free ◽  
New Family ◽  
Three Component Reaction ◽  
High Yields ◽  
First Time ◽  
Derivatives Of

An efficient catalyst-free one-pot three-component reaction was developed for the synthesis of a new family of N- and S-containing spirocyclic compounds. Various derivatives of spirobenzimidazolidine containing an indole scaffold were synthesized for the first time in a modestly toxic solvent and under mild reaction conditions. The reaction times were of the order of several minutes, and all the products were obtained in moderate to high yields (overall yields 58–80%).

Sign in / Sign up

Export Citation Format

Share Document