scholarly journals Bioselectivity Induced by Chirality of New Terpenyl Organoselenium Compounds

Materials ◽  
2019 ◽  
Vol 12 (21) ◽  
pp. 3579 ◽  
Author(s):  
Magdalena Obieziurska ◽  
Agata J. Pacuła ◽  
Angelika Długosz-Pokorska ◽  
Marek Krzemiński ◽  
Anna Janecka ◽  
...  

A series of new chiral benzisoselenazol-3(2H)-ones substituted on the nitrogen atom with three monoterpene moieties—p-menthane, pinane and carane—was synthesized. The compounds were obtained by the reaction of 2-(chloroseleno)benzoyl chloride with an appropriate terpene amine, first synthesized by a multistep methodology starting from the corresponding alcohol (p-menthane system) or alkene (pinene and carene systems). Compounds were tested as antioxidants and anticancer agents. The N-isopinocampheyl-1,2-benzisoselenazol-3(2H)-one was the best peroxide scavenger and antiproliferative agent on the human promyelocytic leukemia cell line HL-60. The N-menthyl-1,2-benzisoselenazol-3(2H)-one revealed the highest anticancer potential towards breast cancer line MCF-7. The influence of structure and chirality on the bio-activity of the obtained organoselenium compounds was thoroughly evaluated.

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 22
Author(s):  
Magdalena Obieziurska ◽  
Agata J. Pacuła ◽  
Anna Laskowska ◽  
Angelika Długosz-Pokorska ◽  
Marek Krzemiński ◽  
...  

Different activity of compounds with the same molecular formula but possessing alternative bonding arrangement or orientation of atoms in space is a very important issue when constructing molecules that can selectively interact with certain domains of the biological target. Herein, we present the synthesis of the new chiral benzisoselenazol-3(2H)-ones substituted on the nitrogen atom with three monoterpene moieties: p-menthane, pinane and carane. All derivatives were obtained by the reaction of an appropriate amine with 2-(chloroseleno)benzoyl chloride. The applied terpenyl amines were first synthetized by a multistep procedure starting from the corresponding alcohol (p-menthane system) or alkene (pinene and carene systems). Finally, all compounds were tested as antioxidants and antiproliferative agents on breast cancer MCF-7 and human promyelocytic leukemia cell line HL-60. The correlation between the structure of the obtained organoselenium compounds, representing examples of various isomers including enantiomers, diastereoisomers and regioisomers, and their bio-activity was thoroughly evaluated.


1996 ◽  
Vol 24 (4) ◽  
pp. 581-587
Author(s):  
Cristiana Zanetti ◽  
Arrnalaura Stammati ◽  
Orazio Sapora ◽  
Flavia Zucco

The aim of this study was to investigate the endpoints related to cell death, either necrosis or apoptosis, induced by four chemicals in the promyelocytic leukemia cell line, HL-60. Cell morphology, DNA fragmentation, cytofluorimetric analysis and oxygen consumption were used to classify the type of cell death observed. In our analysis, we found that not all the selected parameters reproduced the differences observed in the cell death caused by the four chemicals tested. As cell death is a very complex phenomenon, several factors should be taken into account (cell type, exposure time and chemical concentration), if chemicals are to be classified according to differences in the mechanisms more directly involved in cell death.


1979 ◽  
Vol 149 (4) ◽  
pp. 969-974 ◽  
Author(s):  
S J Collins ◽  
F W Ruscetti ◽  
R E Gallagher ◽  
R C Gallo

The HL-60 human promyelocytic leukemia cell line can be induced to terminally differentiate to mature myeloid cells sharing a number of functional characteristics with normal granulocytes including response to chemoattractants, development of complement receptors, phagocytosis, superoxide production, and nitroblue tetrazolium dye reduction. Hence the Me2SO-induced HL-60 cells provide a unique in vitro model for studying various important aspects of human myeloid cell differentiation.


2017 ◽  
Vol 87 ◽  
pp. 39-47 ◽  
Author(s):  
Sylwia Michlewska ◽  
Maksim Ionov ◽  
Dzmitry Shcharbin ◽  
Marta Maroto-Díaz ◽  
Rafael Gomez Ramirez ◽  
...  

Blood ◽  
1986 ◽  
Vol 68 (2) ◽  
pp. 412-416
Author(s):  
SS Jr McCachren ◽  
J Nichols ◽  
RE Kaufman ◽  
JE Niedel

The human promyelocytic leukemia cell line HL-60 is induced to differentiate along a myelocytic pathway by dibutyryl cyclic adenosine monophosphate (dbcAMP). Other cAMP analogs are ineffective as inducing agents. The effect of these compounds on expression of c-myc was investigated using a DNA probe for c-myc to detect RNA transcripts. The dose response and time to commitment for reduction in c-myc expression with dbcAMP was similar to the findings for phenotypic changes. Bromo- cyclic AMP and butyrate alone caused no changes in c-myc expression in 24 hours, but demonstrated dramatic synergism together, suggesting that butyrate contributes in part to the effects of dbcAMP. Evidence for mechanisms of action of cAMP other than activation of the cAMP- dependent protein kinase is reviewed.


Blood ◽  
1981 ◽  
Vol 58 (6) ◽  
pp. 1119-1126 ◽  
Author(s):  
JL Abrahm ◽  
R Smiley

Abstract The tumor promoter, 12-O-tetradecanoylphorbol-13-acetate (TPA), induces macrophage characteristics in the HL-60 promyelocytic leukemia cell line. These same cells can be induced to develop mature myeloid characteristics with a variety of other stimuli. Since normal colony- forming units-culture (CFU C) also have the dual capability of developing colonies with myeloid or monocyte characteristics, the effect of TPA on normal human CFU-C development was studied. To carry out these studies, a method was developed to identify cells histochemically within agar cultures as containing either the myeloid marker, chloroacetate esterase (CAE), or the monocyte marker, nonspecific esterase (NSE). Cells from normal donors were placed into agar cultures with placenta conditioned medium (PCM), TPA in various concentrations, or combinations of PCM and TPA as stimulating materials, and examined after 7–14 days of incubation. TPA alone at concentrations of 5 x 10(-7) M to 10(-9) M stimulated cluster formation. With increasing concentrations of TPA, the percentage of clusters positive for NSE progressively increased, while CAE-positive clusters decreased. I contrast, when TPA at concentrations greater than 10(-9) M was added to PCM, the total number of clusters and colonies decreased. This resulted from a decrease in the number of clusters and colonies that contained the myeloid marker CAE, whereas the number positive for the monocyte marker NSE remained unchanged. These studies demonstrate two effects of TPA on normal CFU-C. In the absence of other sources of colony stimulating activity (CSA), TPA induces clusters. In the presence of PCM, it inhibits the production of myeloid colonies and clusters. Under both conditions, it favors the development of colonies and/or clusters containing predominantly monocytes.


Blood ◽  
1989 ◽  
Vol 73 (2) ◽  
pp. 553-558 ◽  
Author(s):  
R O'Connor ◽  
JG Bradley ◽  
A O'Meara ◽  
TG Cotter

Abstract In this report we describe the production and characterization of a monoclonal antibody to the human promyelocytic leukemia cell line HL- 60. The antibody, NC-2, is of the IgG1 subclass and precipitates a 50- Kd protein from 125I-labeled HL-60 cells. The antigen is insensitive to treatment with trypsin, papain, or neuraminidase. NC-2 did not react with a number of established human cell lines, including Daudi, Molt-4, K562, U937, KG-1, CEM, Raji, and Gash-P. Neutrophils and monocytelike cells derived from HL-60 cells that were induced to differentiate continued to express the antigen. NC-2 reacted with all peripheral- blood cells except erythrocytes from eight (5%) of 150 normal individuals tested. Bone marrow samples from patients with myelogenous leukemias were more frequently reactive with NC-2 than were those from normal individuals (12/33 v 1/10). Family studies indicated that the antigen was inherited in an autosomal-dominant manner. These findings suggest that the expression of the above alloantigen is associated with an increased incidence of leukemia.


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