Publications by authors named "Saeed Bahadorikhalili"

8 Publications

  • Page 1 of 1

The natural-based optimization of kojic acid conjugated to different thio-quinazolinones as potential anti-melanogenesis agents with tyrosinase inhibitory activity.

Bioorg Med Chem 2021 Apr 27;36:116044. Epub 2021 Jan 27.

Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran; Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran. Electronic address:

Melanin pigment and melanogenesis are a two-edged sword. Melanin has a radioprotection role while melanogenesis has undesirable effects. Targeting the melanogenesis pathway, a series of kojyl thioether conjugated to different quinazolinone derivatives were designed, synthesized, and evaluated for their inhibitory activity against mushroom tyrosinase. All the synthesized compounds were screened for their anti-tyrosinase activity and all derivatives displayed better potency than kojic acid as the positive control. In this regard, 5j and 5h as the most active compounds showed an IC value of 0.46 and 0.50 µM, respectively. In kinetic evaluation against tyrosinase, 5j depicted an uncompetitive inhibition pattern. Designed compounds also exhibited mild antioxidant capacity. Moreover, 5j and 5h achieved good potency against the B16F10 cell line to reduce the melanin content, whilst showing limited toxicity against malignant cells. The proposed binding mode of new inhibitors evaluated through molecular docking was consistent with the results of structure-activity relationship analysis.
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http://dx.doi.org/10.1016/j.bmc.2021.116044DOI Listing
April 2021

Bi Metal-Organic Framework (Ce/Ni-BTC) as Heterogeneous Catalyst for the Green Synthesis of Substituted Chromeno[4, 3-b]quinolone under Solvent Free Condition.

Curr Org Synth 2021 Jan 21. Epub 2021 Jan 21.

School of Chemistry, College of Science, University of Tehran, Tehran. Iran.

Aims: Novel bi metal organic framework (b-MOF) is synthesized and used as a heterogeneous catalyst for the synthesis of chromeno[4, 3-b]quinolone derivatives via one pot and solvent free, four-component reaction of dimedone, aromatic aldehydes, 4-hydroxycoumarin and ammonium acetate at 110°C.

Background: b-MOFs can be used as a heterogeneous catalyst in the synthesis of many organic compounds. The active and multi-purpose sites in b-MOFs provide a varied function in their catalytic applications. In this paper, reductive CES method is applied for the synthesis of Ce0.47/Ni0.53-BTC b-MOF. The resulting b-MOF was used as a heterogeneous catalyst for the synthesis of chromeno[4, 3-b]quinolone via one pot and solvent free, four- component reaction of dimedone, aromatic aldehyde, 4-hydroxycoumarin and ammonium acetate at 110 °C.

Method: Ce0.47/Ni0.53-BTC was synthesized in an electrochemical cell composed of a stainless steel foil with size of 5cm×5cm centered between two 5cm×5cm sized graphite plates as the anodes by the cathodic current density of 0.2 A/dm2 and placed in a solution of cerium nitrate (0.3 g), nickel nitrate (0.3 g), H3BTC (0.2 g) and NaNO3 (0.1 g) in ethanol (500 mL). Ce0.47/Ni0.53-BTC (10 mg) was added to a mixture of dimedone (1 mmol), aromatic aldehyde (1 mmol), hydroxycoumarin (1 mmol) and ammonium acetate (1.5 mmol) and stirred at 110 °C under solvent free conditions for 45 min. The reaction evolution was controlled by the TLC (hexane:ethyl acetate, 4:1). Then, boiling ethanol was added to the reaction mixture and stirred at room temperature for 15 min. After the reaction completion, the catalyst was separated by centrifuge. Finally, the reaction mixture was placed in an ice bath, which resulted in white solid product and recrystallized from ethanol to give the pure product.

Result: The b-MOF catalyst showed very good efficiency in the synthesis of the desired compounds and can be easily recovered by centrifuge and reused at least five times without decrease in catalytic activity.

Conclusion: In this report, a novel bi metal-organic framework (Ce0.47/Ni0.53-BTC) is synthesized via cathodic electro- synthesis method. The synthesized b-MOF is fully characterized by several characterization methods. The catalytic activity of Ce0.47/Ni0.53-BTC is investigated in the synthesis of chromeno[4, 3-b]quinolone derivatives via one pot four-component reaction of dimedone, aromatic aldehyde, 4-hydroxycoumarin and ammonium acetate. The reaction optimization results showed that the highest isolated yield was obtained, when the reaction was performed in solvent free conditions at 110 °C. The catalyst showed to be highly efficient in the synthesis of the desired compounds and performing the reaction by various starting materials gave the products in good 3 isolated yields, which proves the generality and the scope of the method. The catalyst could easily be recovered by centrifuge and reused at least five times without decrease in catalytic activity.
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http://dx.doi.org/10.2174/1570179418666210122100240DOI Listing
January 2021

Correction: 4'-Guanidinium-modified siRNA: a molecular tool to control RNAi activity through RISC priming and selective antisense strand loading.

Chem Commun (Camb) 2019 08 7;55(67):10028. Epub 2019 Aug 7.

Translational Chemical Biology Laboratory, Division of Polymer Chemistry, Department of Chemistry-Ångström, Uppsala University, Uppsala, Sweden.

Correction for '4'-Guanidinium-modified siRNA: a molecular tool to control RNAi activity through RISC priming and selective antisense strand loading' by Ganesh N. Nawale et al., Chem. Commun., 2019, 55, 9112-9115.
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http://dx.doi.org/10.1039/c9cc90352fDOI Listing
August 2019

4'-Guanidinium-modified siRNA: a molecular tool to control RNAi activity through RISC priming and selective antisense strand loading.

Chem Commun (Camb) 2019 Jul;55(62):9112-9115

Translational Chemical Biology Laboratory, Division of Polymer Chemistry, Department of Chemistry-Ångström, Uppsala University, Uppsala, Sweden.

We designed novel 4'-C-guanidinocarbohydrazidomethyl-5-methyl uridine (GMU) modified small interfering RNA (siRNA) and evaluated its biophysical and biochemical properties. Incorporation of GMU units significantly increased the thermodynamic stability as well as the enzymatic stability against nucleases in human serum. A gene silencing experiment indicated that GMU modfied siRNA (siRNA6) resulted in ≈4.9-fold more efficient knockdown than unmodified siRNA.
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http://dx.doi.org/10.1039/c9cc04141aDOI Listing
July 2019

The use of magnetic starch as a support for an ionic liquid-β-cyclodextrin based catalyst for the synthesis of imidazothiadiazolamine derivatives.

Int J Biol Macromol 2019 Aug 28;135:453-461. Epub 2019 May 28.

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran 14176, Iran. Electronic address:

In this paper, a novel catalyst is introduced based on the introduction of an ionic liquid onto the β-cyclodextrin. The ionic liquid-β-cyclodextrin was anchored to magnetic starch (denoted βCD-IL@M-Starch) and fully characterized by several methods including TEM, TGA, VSM and FT-IR. The catalyst was used for the synthesis of imidazo[2,1-b][1,3,4]thiadiazol-5-amine and imidazo[1,2-a]pyridin-3-amine derivatives. βCD-IL@M-Starch catalyst showed very good activity in the synthesis of diphenylimidazo[2,1-b][1,3,4]thiadiazol-5-amine derivatives from the corresponding benzaldehyde, semicarbazide, benzaldehydes and isocyanides. The products were obtained in a mild reaction conditions in good isolated yields in the presence of βCD-IL@M-Starch as catalyst. The catalyst showed to be magnetically reusable, and gave very good results in 10 sequential reactions.
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http://dx.doi.org/10.1016/j.ijbiomac.2019.05.197DOI Listing
August 2019

Design, synthesis, docking study, α-glucosidase inhibition, and cytotoxic activities of acridine linked to thioacetamides as novel agents in treatment of type 2 diabetes.

Bioorg Chem 2018 10 30;80:288-295. Epub 2018 Jun 30.

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran. Electronic address:

A novel series of acridine linked to thioacetamides 9a-o were synthesized and evaluated for their α-glucosidase inhibitory and cytotoxic activities. All the synthesized compounds exhibited excellent α-glucosidase inhibitory activity in the range of IC = 80.0 ± 2.0-383.1 ± 2.0 µM against yeast α-glucosidase, when compared to the standard drug acarbose (IC = 750.0 ± 1.5 µM). Among the synthesized compounds, 2-((6-chloro-2-methoxyacridin-9-yl)thio)-N-(p-tolyl) acetamide 9b displayed the highest α-glucosidase inhibitory activity (IC = 80.0 ± 2.0 μM). The in vitro cytotoxic assay of compounds 9a-o against MCF-7 cell line revealed that only the compounds 9d, 9c, and 9n exhibited cytotoxic activity. Cytotoxic compounds 9d, 9c, and 9n did not show cytotoxic activity against the normal human cell lines HDF. Kinetic study revealed that the most potent compound 9b is a competitive inhibitor with a K of 85 μM. Furthermore, the interaction modes of the most potent compounds 9b and 9f with α-glucosidase were evaluated through the molecular docking studies.
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http://dx.doi.org/10.1016/j.bioorg.2018.06.035DOI Listing
October 2018

Peptide functionalized poly ethylene glycol-poly caprolactone nanomicelles for specific cabazitaxel delivery to metastatic breast cancer cells.

Mater Sci Eng C Mater Biol Appl 2017 Nov 20;80:301-312. Epub 2017 May 20.

Department of Pharmaceutics, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran; Nanotechnology Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran. Electronic address:

Metastatic cancer is responsible for 90% of deaths in world. Usage of nano-carriers improve the delivery and efficacy of chemotherapeutic agents. Recent studies suggest that decoration of the surface of nano-carriers with various targeting agents may further improve their overall therapeutic efficacy. Using specified peptides in targeted drug delivery is a key point in recent researches. In this study, tumor metastasis targeting (TMT) homing peptide was applied as a targeting group to improve specific drug delivery to tumor cells. TMT peptide is conjugated to poly ethylene glycol-poly caprolactone (PEG-PCL) micellar nanoparticles as carriers for targeted delivery of cabazitaxel to metastatic breast cancer cells. Synthesis of PEG-PCL copolymer was performed by amidation reaction between carboxylic acid group of PEG and amine group of PCL. Nanomicelles were prepared via solvent evaporation method. TMT peptide was covalently conjugated onto nanomicelles through the amine group of PEG. TMT-PEG-PCL nanoparticles were analyzed by Fourier transform infrared spectroscopy (FTIR), scanning electron microscope (SEM), dynamic light scattering (DLS), gel permeation chromatography (GPC) and nuclear magnetic resonance (NMR). Toxicity and cellular uptake of nanomicelles were investigated by in vitro cytotoxicity assays and confocal scanning microscopy in MCF-7 (non-metastatic breast cancer cells) and MDA-MB-231 (metastatic breast cancer cells). The final nanomicelles had about 110nm mean size and encapsulation efficiency of 82.5%. Treatment of metastatic breast cancer cells with targeted nanomicelles significantly increased the necrosis rate to 65%, compared to 33% in non-targeted nanomicelles and 8% in control group. The MDA-MB-231 cells treated with targeted nanomicelles exhibited a strong increase in the fluorescence intensity of coumarin in comparison to the cells treated with non-targeted nanomicelles (p<0.001). It could be concluded that the present carrier has the potential to be considered in treatment of metastatic breast cancer cells.
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http://dx.doi.org/10.1016/j.msec.2017.05.126DOI Listing
November 2017

Ionic liquid-functionalized magnetic nanostructures as an efficient catalyst for the synthesis of 6H-chromeno[4,3-b]quinolin-6-ones.

Mol Divers 2017 Aug 5;21(3):597-609. Epub 2017 May 5.

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, 14176, Iran.

A novel imidazole ionic liquid (IL)-functionalized [Formula: see text]-[Formula: see text] ([Formula: see text]) is prepared by the functionalization of [Formula: see text] by 1-butyl-3-(3-trimethoxypropyl)-1H-imidazol-3-ium chloride as the IL moiety. The catalyst is characterized by transmission electron microscopy, scanning electron microscope, vibrating sample magnetometer, dynamic light scattering and Fourier transform infrared spectroscopy. [Formula: see text] showed good activity in the synthesis of 6H-chromeno[4,3-b]quinolin-6-one derivatives via multicomponent reaction of 4-hydroxycoumarin, anilines and benzaldehydes. The nanocatalyst is magnetically separable and easily recoverable and showed successful activity up to 10 runs.
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http://dx.doi.org/10.1007/s11030-017-9746-7DOI Listing
August 2017