Non-cytotoxic 3-Acetylcoumarin as an Attractive Target for Human Monoamine Oxidase (HMAO) Enzymes.

Background/aim: Coumarins are a broad class of naturally occurring oxygen-heterocyclic compounds found in plants with diverse biological properties, making them attractive for evaluation as novel therapeutic agents. We herein report the in vitro cytotoxic and monoamine oxidase (MAO) inhibitory activities of 3-acetylcoumarins ().

Materials And Methods: The cytotoxic activity was evaluated using crystal violet dye binding assay, and those compounds unable to induce cytotoxicity were further tested for the monoamine oxidase (MAO) activity using the MAO-GloTM kit.

7,8-Diacetoxy-3-(4-methylsulfonylphenyl)-4-phenylcoumarin Induces ROS-dependent Cell Death in the A549 Human Lung Cancer Cell Line.

Background/aim: Coumarins comprise of a very large class of naturally occurring compounds with growing interest in their synthesis and possible applications in the treatment of various diseases. We herein report the in-vitro cytotoxic activity of 3,4-Diarylcoumarins (4a-i) in A549 (lung) and PC-3 (prostate) cancer cell lines.

Materials And Methods: The cytotoxic activity was evaluated using crystal violet dye-binding.

Identification of 7,8-dihydroxy-3-phenylcoumarin as a reversible monoamine oxidase enzyme inhibitor.

We herein report the biological evaluation of 3-arylcoumarin derivatives (3a-l) as potential human monoamine oxidase-A and -B (hMAO-A and hMAO-B) inhibitors. The result indicated that 7,8-dihydroxy-3-(4-nitrophenyl)coumarin (3j) was most effective against MAO-A (inhibition concentration [IC ] = 6.46 ± 0.

7,8-Dihydroxy-3-arylcoumarin Induces Cell Death Through S-Phase Arrest in MDA-MB-231 Breast Cancer Cells.

Background/aim: Coumarins remain one of the most versatile classes of compounds for anticancer drug design and discovery. The present study aimed to evaluate the in vitro cytotoxic activity of 7,8-Dihydroxy-3-arylcoumarin derivatives (7a-i) in A549, MDA-MB-231and PC-3 cancer cell lines.

Materials And Methods: Cell viability, cell-cycle progression and regulatory protein expression were evaluated using crystal violet dye-binding assay, flow cytometry and western blot analysis.

7,8-Dihydroxy-3-(4-nitrophenyl)coumarin induces cell death via reactive oxygen species-independent S-phase cell arrest.

We herein report the synthesis and in vitro cytotoxicity of 3-arylcoumarin derivatives (6a-f and 7a-f) in human liver (HepG2), prostate (LNCap), and pancreatic (BxPC3) cancer cell lines. Among the tested compounds, 7,8-dihydroxy-3-(4-nitrophenyl) coumarin (7b) showed the highest cytotoxicity in the HepG2 cell line. The mechanism of cytotoxic action indicated that compound (7b) arrested HepG2 cells at the S phase of the cell cycle progression, induced loss of mitochondrial membrane potential, and caused reactive oxygen species (ROS)-independent cell death.

Identification of 7,8-Diacetoxy-3-Arylcoumarin Derivative as a Selective Cytotoxic and Apoptosis-inducing Agent in a Human Prostate Cancer Cell Line.

Background/aim: Coumarins are a member of the benzopyrone family of compounds with diverse and interesting pharmacological properties. In the present study, we report the in vitro cytotoxicity evaluation of 7,8-Diacetoxy-3-arylcoumarin derivatives (5a-h) in human prostate (PC-3) and breast (MDA-MB-231) cancer cell lines.

Materials And Methods: The cytotoxic activity was evaluated using crystal violet dye-binding assay.

In vitro evaluation of 3-arylcoumarin derivatives in A549 cell line.

Unlabelled: Coumarins are naturally-occurring compounds with diverse and interesting biological activities. In the present study, we evaluated the in vitro cytotoxic effect of 8-(acetyloxy)-3-[4-(acetyloxy)phenyl]-2-oxo-2H-chromen-7-yl acetate (6); 8-(acetyloxy)-3-(4-methanesulfonyl phenyl)-2-oxo-2H-chromen-7-yl acetate (7); 4-(2-oxo-2H-chromen-3-yl)phenyl acetate (8); 3-(4-methanesulfonylphenyl)-2H-chromen-2-one (9); 4-(4-methyl-2-oxo-2H-chromen-3-yl)phenyl acetate (10); 3-(4-methanesulfonylphenyl)-4-methyl-2H-chromen-2-one (11); 8-(acetyloxy)-3-[4-(acetyloxy)phenyl]-4-methyl-2-oxo-2H-chromen-7-yl acetate (12); and 5-(acetyloxy)-3-[4-(acetyloxy) phenyl]-2-oxo-2H-chromen-7-yl acetate (13) in human lung (A549) cancer and normal lung (MRC-9) cell lines at different concentrations for 48 h using crystal violet dye binding assay. The cytotoxic effect of these coumarin derivatives were compared to the standard drug, docetaxel.

Synthesis and in vitro evaluation of 3-(4-nitrophenyl)coumarin derivatives in tumor cell lines.

Coumarins are naturally-occurring compounds that have attracted considerable interest due to their numerous biological activities depending on their pattern of substitution on the coumarin molecule. In this present investigation, we synthesized 3-(4-nitrophenyl)coumarin derivatives (9a-e) and evaluated their in vitro cytotoxic effect on human lung (A549), breast (MDA-MB-231) and prostate (PC3) cancer cell lines for 48 h using crystal violet dye binding assay. Cytotoxic effects of the most active compound on normal human lung (MRC-9) and breast (MCF-10A) cell lines, cell cycle analysis using flow cytometry and mitochondrial membrane potential (MMP) using Tetramethyl Rhodamine Methyl Ester (TMRM; rhodamine-123) fluorescent dye were also examined.

Cytotoxic activity of N, N'-Bis (2-hydroxybenzyl) ethylenediamine derivatives in human cancer cell lines.

Background: Compounds containing ethylenediamine (-NCH2CH2N-) moiety are known to exhibit antimicrobial, -fungal, -bacterial, -tuberculosis and -cancer activities.

Materials And Methods: In the present study, we evaluated the in vitro cytotoxic activity of N,N'-bis(2-hydroxybenzyl)- (6), N,N'-bis(5-bromo-2-hydroxybenzyl)- (7) and N,N'-bis(5-chloro-2-hydroxybenzyl) (8)- ethylenediamine dihydrochlorides; and N,N'-bis(2-hydroxybenzyl)- (9), N,N'-bis(5-bromo-2-hydroxybenzyl)- (10) and N,N'-bis(5-chloro-2-hydroxybenzyl) (11)- ethylenediamine toward human lung (A549), breast (MDA-MB-231) and prostate (PC3) cancer cell lines after 24-h treatment using crystal violet dye binding assay. Effects on the cell cycle the using flow cytometry, and mitochondrial membrane potential using rhodamine-123 florescent dye were also evaluated.

Coumarin-based benzopyranone derivatives induced apoptosis in human lung (A549) cancer cells.

In the present investigation, we report on the possible underlying mechanism for the cytotoxicity of compounds: 3-(4-(2-(dimethylamino)ethoxy)-phenyl)-7-methoxy-4-phenyl coumarin 5, 3-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-7-methoxy-4-phenylcoumarin 6, and 3-(4-(2-(diethylamino) ethoxy)phenyl)-7-methoxy-4-methylcoumarin 7 in the human lung (A549) cancer cell line, using Ray Biotech's Human Apoptosis Arrays and apoptotic protein antibodies. Apoptosis array results showed differential apoptotic proteins expression in the extracts of cells treated with compounds 5-7. Western blotting demonstrated that compound 5 induced apoptosis and caused cell death in the A549 cell line via an increase (up-regulation) in Bax protein expression (pro-apoptotic pathway) and a slight decrease (down-regulation) in Bcl-2 protein expression (anti-apoptotic pathway) after 6 h of treatment.

Synthesis and biological activity of 3-N-substituted estrogen derivatives as breast cancer agents.

3-N-substituted-estrogen derivatives were synthesized and characterized. Their antiproliferative activities against human ER (+) MCF-7 (Breast), ER (-) MDA-MB-231 (breast) and Ishikawa (endometrial) cancer cell lines were determined after 72 hours drug exposure employing CellTiter-Glo assay at concentrations ranging from (0.01-100,000 nM).

Cytotoxic activity of new acetoxycoumarin derivatives in cancer cell lines.

Background: Coumarin and their derivatives are important and useful compounds with diverse pharmacological properties. In the present study, we evaluated the in vitro cytotoxic activity of new acetoxycoumarin derivatives: 4-(7-methoxy-4-methyl-2-oxo-2H-chromen-3-yl)phenyl acetate (1), 4-(1-methyl-3-oxo-3H-benzo[f]chromen-2-yl)phenyl acetate (2), 4-(6-propionamido-4-methyl-2-oxo-2H-chromen-3-yl) phenyl acetate (3), 4-(7-acetoxy-2-oxo-4-phenyl-2H-chromen-3-yl)phenyl acetate (4), 4-(2-oxo-4-phenyl-2H-chromen-3-yl)phenyl acetate (5), 4-(6-bromo-2-oxo-4-phenyl-2H-chromen-3-yl)phenyl acetate (6), 4-(7-(diethylamino)-4-methyl-2-oxo-2H-chromen-3-yl)phenyl acetate (7), 4-(6,8-dibromo-4-methyl-2-oxo-2H-chromen-3-yl)phenyl acetate (8) against A549 human lung cancer, CRL 1548 rat liver cancer and CRL 1439 normal rat liver cells.

Materials And Methods: The cytotoxic activity was evaluated by crystal violet dye-binding assay.

In-vitro antiproliferative activity of benzopyranone derivatives in comparison with standard chemotherapeutic drugs.

The cytotoxic activities of five new benzopyranone derivatives containing basic amino side chain are described. Their cytotoxicities against ER(+) MCF-7 and ER(-) MDA-MB-231 human breast cancer cell lines, and Ishikawa human endometrial cell line were determined after 72 h drug exposure employing CellTiter-Glo assay at concentrations ranging from 0.01-1.

Synthesis and antiproliferative activity of new coumarin-based benzopyranone derivatives against human tumor cell lines.

The synthesis and antiproliferative activity of new coumarin-based benzopyranone derivatives containing basic amino side chain are described. The cytotoxicities against A549 and MCF-7 human cancerous cell lines were determined after 24, 48, 72 h drug exposure employing MTT assay at concentrations ranging from 0-100 μM. The antiproliferative activities of these compounds were compared to tamoxifen (TAM), 4-hydroxytamoxifen (4-OHT), raloxifene (RAL), 17β-estradiol (E2) and Diethylstilbestrol (DES).

In vitro cytotoxicity of benzopyranone derivatives with basic side chain against human lung cell lines.

Background: Coumarins belong to an important group of useful drugs with diverse pharmacological properties. In the present study, the in vitro cytotoxicity of new coumarin-based benzopyranone derivatives containing diethylaminoethoxy (5), dimethylaminoethoxy (6), morpholinoethoxy (7), piperidinylethoxy (8) and pyrrolidinylethoxyl (9) amino side chain against human carcinoma (A549) and normal (LL47) lung cell lines was evaluated.

Materials And Methods: The cytotoxicity was evaluated by crystal violet dye binding assay.

Synthesis and Antimicrobial Activity of N,N'-Bis(2-hydroxylbenzyl)-1,2-ethanediamine Derivatives.

A series of N,N'-Bis(2-hydroxylbenzyl)-1,2-ethanediamine derivatives and its schiff bases were synthesized, characterized and screened for in vitro antimicrobial activity against Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella enterica. Result indicated that the ethylenediamine derivatives, N,N'-Bis(2-hydroxy-5-bromobenzyl)-1,2-ethanediamine (21), and N,N'-Bis(2-hydroxy-5-chlorobenzyl)-1,2-ethanediamine (22) showed the most favorable antimicrobial activity exhibiting LC(50) of 11.6 and 8.

Synthesis and antiproliferative activity of coumarin-estrogen conjugates against breast cancer cell lines.

The syntheses and cytotoxic activity of coumarin-estrogen conjugates are described. In vitro results indicated that conjugates 10, 11 and 13 show growth inhibitory activities at 5-dose concentration (100, 10, 1, 0.1, 0.

A review of coumarin derivatives in pharmacotherapy of breast cancer.

The coumarin (benzopyran-2-one, or chromen-2-one) ring system, present in natural products (such as the anticoagulant warfarin) that display interesting pharmacological properties, has intrigued chemists and medicinal chemists for decades to explore the natural coumarins or synthetic analogs for their applicability as drugs. Many molecules based on the coumarin ring system have been synthesized utilizing innovative synthetic techniques. The diversity oriented synthetic routes have led to interesting derivatives including the furanocoumarins, pyranocoumarins, and coumarin sulfamates (COUMATES), which have been found to be useful in photochemotherapy, antitumor and anti-HIV therapy, and as stimulants for central nervous system, antibacterials, anti-inflammatory, anti-coagulants, and dyes.

Medicinal chemistry and emerging strategies applied to the development of selective estrogen receptor modulators (SERMs).

Selective estrogen receptor modulators (SERMs), known previously as "antiestrogens", are a new category of therapeutic agents used for the prevention and treatment of diseases such as osteoporosis and breast cancer. SERMs act as ER-agonist in some tissues while acting as ER-antagonist in others based on conformational change of the receptors, particularly at the helix 12. Currently, there are two classes of clinically approved SERMs; triphenylethylene derivatives (e.

Does the DABCO-catalysed reaction of 2-hydroxybenzaldehydes with methyl acrylate follow a Baylis-Hillman pathway?

Evidence is presented which supports the intermediacy of dipolar Baylis-Hillman-type adducts in the synthesis of coumarin and chromene derivatives from the reaction of 2-hydroxybenzaldehydes with methyl acrylate in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO).