Synthesis and Anticancer Activity Evaluation of 5-[2-Chloro-3-(4-nitrophenyl)-2-propenylidene]-4-thiazolidinones
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. In Vitro Evaluation of the Anticancer Activity
3. Materials and Methods
3.1. General Information
3.2. Synthesis of 5-[(Z,2Z)-2-chloro-3-(4-nitrophenyl)-2-propenylidene]-thiazolidinone derivatives (2a-l)
3.3. Crystal Structure Determination of 6-{5-[(Z,2Z)-2-chloro-3-(4-nitrophenyl)-2-propenylidene]- 4-oxo-2-thioxothiazolidin-3-yl}hexanoic Acid Dimethylaminoformamide Solvate (2i·DMF)
3.4. In Vitro Evaluation of the Anticancer Activity According DTP NCI Protocol
3.5. Cell Viability Assay (AGS, DLD-1, MCF-7 and MDA-MB-231 Cell Lines; Human Blood Lymphocytes)
3.6. Isolation of Human Blood Lymphocytes and Their Activation
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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D—H∙∙∙A | D—H | H∙∙∙A | D∙∙∙A | D—H∙∙∙A |
---|---|---|---|---|
O14—H14∙∙∙O29 | 0.95 (3) | 1.63 (3) | 2.5758 (16) | 171 (3) |
C11—H11A∙∙∙O13 i | 0.99 | 2.55 | 3.5287 (19) | 172 |
C11—H11A∙∙∙O15 ii | 0.99 | 2.47 | 3.135 (2) | 125 |
C21—H22∙∙∙C118 | 0.95 | 2.51 | 3.2049 (15) | 130 |
C22—H22∙∙∙S6 iii | 0.95 | 2.75 | 3.6734 (16) | 164 |
C25—H25∙∙∙O29 iv | 0.95 | 2.50 | 3.4332 (18) | 169 |
Cell line/comp. | 2b | 2c | 2f | 2h | 2j |
---|---|---|---|---|---|
GI50/TGI/LC50, μM | GI50/TGI/LC50, μM | GI50/TGI/LC50, μM | GI50/TGI/LC50, μM | GI50/TGI/LC50, μM | |
Leukemia | |||||
CCRF-CEM | 1.97/21.5/>50 | 4.42/35.3/>100 | 2.92/>100/>100 | ||
HL-60(TB) | 1.21/14.4/>50 | 5.32/23.3/87.2 | 0.485/4.48/>100 | 0.347/1.87/>100 | |
K-562 | 1.44/42.5/>50 | 3.98/25.5/>100 | 0.521/>100/>100 | 0.212/2.83/>100 | 3.01/>100/>100 |
MOLT-4 | 1.74/14.2/>50 | 3.20/8.95/52.5 | 0.389/>100/>100 | 0.016/19.7/>100 | 3.14/>100/>100 |
RPMI-8226 | 1.54/20.6/>50 | 2.38/6.32/>100 | <0.01/0.264/>100 | 0.138/1.30/>100 | 3.22/>100/>100 |
SR | 1.18/7.96/>50 | 3.67/12.0/>100 | 0.01/0.138/>100 | <0.01/1.41/>100 | 2.45/>100/>100 |
Non-Small Cell Lung Cancer | |||||
A549/ATCC | 8.18/>50/>50 | 18.9/42.6/96.1 | 2.25/6.47/>100 | 1.76/7.62/>100 | 3.46/>100/>100 |
EKVX | 2.76/>50/>50 | 23.7/47.7/96.1 | 2.37/16.2/>100 | 0.334/4.01/55.6 | 2.59/7.29/>100 |
HOP-62 | 15.4/33.1/>50 | 17.2/39.7/91.9 | 2.61/5.22/11.6 | 6.54/19.9/52.8 | 2.31/6.75/>100 |
HOP-92 | 8.48/>50/>50 | 8.53/39.4/>100 | 4.81/18.3/50.7 | 2.36/5.71/>100 | |
NCI-H226 | 6.28/20.0/> 50 | 12.0/31.8/84.2 | 1.58/3.27/6.76 | ||
NCI-H23 | 3.27/13.4/45.5 | 16.6/31.6/60.3 | 1.48/3.11/6.52 | 1.44/3.22/7.19 | 2.13/4.86/>100 |
NCI-322M | 6.51/18.8/>50 | 87.6/>100/>100 | 2.49/9.02/>100 | 2.83/10.9/63.4 | >100/>100/>100 |
NCI-H460 | 3.95/18.6/>50 | 15.0/32.3/69.5 | 0.754/>100/>100 | 0.804/3.32/>100 | 2.19/>100/>100 |
NCI-H522 | 3.19/13.1/42.3 | 16.3/32.9/66.2 | 1.72/4.47/29.5 | ||
Colon Cancer | |||||
Colo 205 | 4.04/17.4/>50 | 56.2/>100/>100 | 4.34/>100/>100 | 0.350/>100/>100 | 2.45/>100/>100 |
HCC-2998 | 5.43/11.7/25.0 | 1.96/3.50/6.27 | |||
HCT-116 | 2.93/11.0/33.7 | 2.73/6.51/23.3 | 1.27/2.96/6.92 | 0.270/1.19/>100 | 2.01/5.47/56.7 |
HCT-15 | 1.79/8.81/25.4 | 16.6/33.0/65.7 | 0.409/>100/>100 | 0.230/2.96/>100 | 1.92/4.58/>100 |
HT-29 | 1.48/9.48/>50 | 2.14/>100/>100 | 1.25/2.77/>100 | 2.84/8.47/>100 | |
KM12 | 5.27/14.6/40.4 | 20.6/59.1/>100 | 2.85/>100/>100 | 0.639/29.5/>100 | 2.06/4.35/9.16 |
SW-620 | 1.94/7.62/23.5 | 7.24/>100/>100 | 0.037/1.52/>100 | <0.01/3.25/>100 | 2.10/4.39/>100 |
CNS Cancer | |||||
SF-268 | 5.24/18.9/>50 | 17.0/41.3/>100 | 2.55/34.5/>100 | 2.12/9.74/>100 | 2.21/>100/>100 |
SF-295 | 8.46/37.9/>50 | 18.0/37.3/77.1 | 2.26/13.8/>100 | 3.36/21.6/>100 | 2.59/7.85/>100 |
SF-539 | 9.39/23.1/>50 | 25.9/57.4/>100 | 0.0252/0.242/28.1 | <0.01/0.267/25.8 | 2.74/>100/>100 |
SNB-19 | 8.10/21.4/>50 | 48.3/>100/>100 | 10.0/32.0/97.5 | 0.658/26.3/83.7 | 1.85/> 100/>100 |
SNB-75 | 7.59/23.5/>50 | 25.1/>100/>100 | 12.5/46.0/>100 | 1.96/5.37/>100 | |
U251 | 3.09/9.73/22.1 | 8.03/24.5/65.8 | 0.368/3.06/38.9 | 0.149/2.00/>100 | 1.72/3.52/7.21 |
Melanoma | |||||
LOX IMVI | 6.60/15.4/36.0 | 13.0/28.8/63.8 | 1.17/3.70/>100 | 0.161/0.515/>100 | 1.64/3.26/6.46 |
MALME-3M | 4.93/14.9/44.6 | 25.0/60.4/>100 | 6.53/27.6/94.5 | 9.70/61.9/>100 | 2.13/4.82/>100 |
M14 | 8.87/32.2/>50 | 16.2/35.7/78.5 | 1.90/3.73/7.32 | 1.66/3.58/7.74 | 2.53/>100/>100 |
SK-MEL-2 | 8.07/26.9/>50 | 19.0/36.4/69.8 | 0.802/4.93/65.1 | 1.87/4.50/>100 | |
SK-MEL-28 | 5.87/12.3/25.9 | 4.49/47.7/>100 | 3.59/23.6/89.5 | 2.16/4.68/11.6 | |
SK-MEL-5 | 3.82/10.6/24.0 | 19.4/38.3/75.6 | <0.01/<0.01/3.41 | 0.0193/0.0849/1.88 | 1.68/3.06/5.60 |
UACC-62 | 5.75/12.5/27.2 | 13.6/28.1/58.0 | 1.69/3.85/8.78 | 1.23/2.97/7.18 | 2.00/4.85/30.2 |
Ovarian Cancer | |||||
IGROV1 | 7.28/21.1/>50 | 13.3/28.0/58.9 | 1.63/6.13/>100 | 0.794/3.68/43.1 | 2.99/>100/>100 |
OVCAR-3 | 1.65/8.08/26.6 | 0.821/12.7/41.1 | 0.977/41.8/>100 | 0.135/6.05/66.6 | 1.76/3.51/6.98 |
OVCAR-4 | 1.95/11.7/>50 | 2.63/>100/>100 | 2.66/14.9/56.2 | 3.21/>100/>100 | |
OVCAR-5 | 11.1/19.5/32.4 | 15.1/36.2/86.6 | 2.82/7.91/>100 | ||
OVCAR-8 | 5.08/15.6/47.9 | 1.98/4.08/8.38 | 1.14/22.9/>100 | 0.244/11.5/>100 | 3.13/>100/>100 |
SK-OV-3 | 13.0/>50/>50 | 59.6/>100/>100 | 10.2/41.5/>100 | 6.83/27.4/77.6 | 4.13/>100/>100 |
Renal Cancer | |||||
786-0 | 9.40/18.8/37.6 | 12.1/30.7/77.8 | 2.04/3.83/7.18 | 1.13/2.47/5.42 | 2.10/5.01/>100 |
A498 | 4.57/12.2/30.9 | 13.0/29.6/67.3 | 1.65/3.24/6.37 | ||
ACHN | 3.64/11.8/31.7 | 15.6/29.7/56.4 | 1.70/3.51/7.27 | 1.02/2.42/5.76 | 1.80/3.30/6.04 |
CAKI-1 | 7.14/25.2/>50 | 3.11/11.2/>100 | 4.44/>100/>100 | 0.485/6.14/47.1 | 2.28/5.09/16.7 |
RXF 393 | 0.105/0.341/1.73 | 1.54/3.02/5.93 | |||
SN12C | 4.11/18.0/>50 | 29.0/>100/>100 | 1.98/4.41/>100 | 1.05/2.99/8.48 | 2.84/>100/>100 |
TK-10 | 10.6/23.2/>50 | 28.0/69.6/>100 | 4.87/29.0/>100 | 2.33/16.9/92.0 | 2.43/>100/>100 |
UO-31 | 4.12/21.8/>50 | 17.5/32.2/59.1 | 2.08/3.98/>100 | 0.812/2.43/6.31 | 1.59/3.10/6.05 |
Prostate Cancer | |||||
PC-3 | 4.68/>50/>50 | 8.10/45.8/>100 | 2.29/84.8/>100 | 0.712/13.7/41.9 | 2.53/7.98/>100 |
DU-145 | 7.09/14.2/28.4 | 21.7/52.8/>100 | 0.666/5.81/50.1 | 0.421/3.48/52.3 | 2.06/4.56/11.7 |
Breast Cancer | |||||
MCF-7 | 2.14/38.0/>50 | 4.08/19.8/83.7 | 0.401/28.0/>100 | 0.239/14.4/>100 | 2.38/10.7/>100 |
NCI/ADR-Res | 5.71/18.3/>50 | 6.55/20.8/61.7 | 2.17/6.13/>100 | 0.407/2.11/6.43 | |
MDA-MB-231/ATCC | 8.16/28.1/>50 | 10.0/35.4/>100 | 2.18/12.2/92.1 | 1.08/4.86/25.9 | 3.35/>100/>100 |
HS 578T | 1.42/12.1/>50 | 29.5/>100/>100 | 4.37/>100/>100 | ||
MDA-MB-435 | 8.57/47.9/>50 | 20.3/41.9/86.3 | 3.50/7.71/>100 | 1.25/4.12/29.3 | |
BT-549 | 1.47/4.74/27.2 | 27.3/76.0/>100 | 1.55/7.71/>100 | 0.247/0.920/36.3 | 1.79/4.17/>100 |
T-47D | 3.21/>50/>50 | 24.5/65.3/>100 | 1.55/7.71/>100 | 0.363/>100/>100 | 1.50/3.71/>100 |
MDA-MB-468 | 1.39/3.28/7.71 |
Compound/Disease | 2b | 2c | 2f | 2h | 2j | ||||||
---|---|---|---|---|---|---|---|---|---|---|---|
MG_MID, μM | SI | MG_MID, μM | SI | MG_MID, μM | SI | MG_MID, μM | SI | MG_MID, μM | SI | ||
Leukemia | GI50 | 1.51 | 3.17 | 3.83 | 4.70 | 0.283 | 9.89 | 0.145 | 10.83 | 2.95 | 1.39 |
TGI | 20.2 | 1.00 | 18.6 | 2.32 | 41.0 | 0.78 | 5.42 | 2.45 | >100 | <0.41 | |
LC50 | >50 | <0.87 | 90 | 0.91 | >100 | <0.81 | >100 | <0.65 | >100 | <0.74 | |
Non-Small Cell Lung Cancer | GI50 | 3.79 | 1.26 | 25.9 | 0.69 | 2.93 | 0.96 | 2.65 | 0.59 | 13.1 | 0.31 |
TGI | 29.7 | 0.68 | 44.8 | 0.96 | 26.6 | 1.21 | 9.61 | 1.38 | 36.9 | 1.10 | |
LC50 | 48.6 | 0.90 | 83.0 | 0.98 | 74.0 | 1.09 | 61.4 | 1.06 | 92.9 | 0.80 | |
Colon Cancer | GI50 | 3.27 | 1.46 | 20.7 | 0.87 | 1.84 | 1.52 | 0.458 | 3.43 | 2.19 | 1.87 |
TGI | 11.5 | 1.77 | 59.7 | 0.72 | 67.4 | 0.48 | 23.3 | 0.57 | 18.7 | 2.17 | |
LC50 | 35.4 | 1.23 | 77.8 | 1.05 | 84.5 | 0.96 | >100 | <0.65 | 67.4 | 1.10 | |
CNS Cancer | GI50 | 6.98 | 0.69 | 23.4 | 0.77 | 6.72 | 0.42 | 3.13 | 0.50 | 2.18 | 1.88 |
TGI | 22.4 | 0.91 | 52.1 | 0.83 | 30.6 | 1.05 | 17.7 | 0.75 | 3.52 | 11.53 | |
LC50 | 45.4 | 0.96 | 88.6 | 0.92 | 77.4 | 1.04 | 84.9 | 0.77 | 7.21 | 10.25 | |
Melanoma | GI50 | 5.57 | 0.86 | 17.7 | 1.02 | 2.63 | 1.06 | 2.45 | 0.64 | 2.00 | 2.05 |
TGI | 16.1 | 1.26 | 38.0 | 1.13 | 14.4 | 2.23 | 13.9 | 0.96 | 17.9 | 2.27 | |
LC50 | 36.8 | 1.18 | 74.3 | 1.10 | 52.3 | 1.54 | 53.1 | 1.22 | 50.6 | 1.46 | |
Ovarian Cancer | GI50 | 6.68 | 0.72 | 18.2 | 0.99 | 3.32 | 0.84 | 2.13 | 0.74 | 3.00 | 1.36 |
TGI | 21.0 | 0.97 | 36.2 | 1.19 | 42.5 | 0.76 | 12.7 | 1.05 | 68.6 | 0.59 | |
LC50 | 42.8 | 1.02 | 59.0 | 1.38 | >100 | <0.81 | 68.7 | 0.95 | 84.5 | 0.87 | |
Renal Cancer | GI50 | 6.23 | 0.77 | 16.9 | 1.07 | 2.85 | 0.98 | 0.99 | 1,59 | 2.03 | 2.01 |
TGI | 18.7 | 1.09 | 43.3 | 1.00 | 24.1 | 1.34 | 4.81 | 2.77 | 27.8 | 1.46 | |
LC50 | 42.9 | 1.01 | 80.1 | 1.02 | 69.1 | 1.17 | 23.8 | 2.73 | 42.6 | 1.73 | |
Prostate Cancer | GI50 | 5.89 | 0.81 | 14.9 | 1.21 | 1.48 | 1.89 | 0.567 | 2.77 | 2.30 | 1.78 |
TGI | 32.1 | 0.63 | 45.3 | 0.95 | 45.3 | 0.71 | 8.59 | 1.55 | 6.27 | 6.48 | |
LC50 | 39.2 | 1.11 | 75.1 | 1.09 | 75.1 | 1.08 | 47.1 | 1.38 | 55.9 | 1.32 | |
Breast Cancer | GI50 | 4.38 | 1.09 | 17.5 | 1.03 | 1.89 | 1.48 | 0.598 | 2.63 | 24.6 | 0.17 |
TGI | 28.4 | 0.71 | 51.3 | 0.84 | 11.6 | 2.78 | 21.1 | 0.63 | 37.0 | 1.10 | |
LC50 | 46.7 | 0.93 | 90.2 | 0.91 | 98.7 | 0.82 | 49.6 | 1.31 | 84.6 | 0.87 | |
60 lines MG_MID | GI50 | 4.79 | 18.0 | 2.80 | 1.57 | 4.09 | |||||
TGI | 20.3 | 43.1 | 32.2 | 13.3 | 40.6 | ||||||
LC50 | 43.5 | 81.7 | 80.8 | 65.0 | 73.9 |
Compound | Cell line, GI50, μM | |||
---|---|---|---|---|
AGS | DLD-1 | MCF-7 | MDA-MB-231 | |
2a | 18.71 | 13.98 | 18.03 | 13.89 |
2b | 7.86 | 8.39 | 4.79 | 10.56 |
2c | 4.43 | 6.34 | 3.60 | 1.59 |
2d | 4.08 | 5.47 | 4.45 | 3.11 |
2e | 17.05 | 16.00 | 17.92 | 15.83 |
2g | 17.99 | 27.49 | 26.40 | 16.84 |
2h | 2.69 | 3.67 | 3.62 | 1.63 |
2i | 3.20 | 9.22 | 1.73 | 0.95 |
2k | 13.05 | 10.00 | 18.08 | 15.30 |
2l | 12.57 | 9.19 | 21.23 | 17.50 |
Compound | Leukemia Cell Line TI (Therapeutic Index) | |||||
---|---|---|---|---|---|---|
HL-60(TB) | K-562 | MOLT-4 | RPMI-8226 | SR | Leukemia Panel | |
2f | >206.19 | >191.94 | >257.07 | >10,000 | >10,000 | >353.36 |
2h | 157.18 | 257.26 | 3408.75 | 395.22 | 5454 | 376.14 |
2j | n/a | 16.27 | 15.59 | 15.21 | 19.99 | 16.60 |
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Buzun, K.; Kryshchyshyn-Dylevych, A.; Senkiv, J.; Roman, O.; Gzella, A.; Bielawski, K.; Bielawska, A.; Lesyk, R. Synthesis and Anticancer Activity Evaluation of 5-[2-Chloro-3-(4-nitrophenyl)-2-propenylidene]-4-thiazolidinones. Molecules 2021, 26, 3057. https://doi.org/10.3390/molecules26103057
Buzun K, Kryshchyshyn-Dylevych A, Senkiv J, Roman O, Gzella A, Bielawski K, Bielawska A, Lesyk R. Synthesis and Anticancer Activity Evaluation of 5-[2-Chloro-3-(4-nitrophenyl)-2-propenylidene]-4-thiazolidinones. Molecules. 2021; 26(10):3057. https://doi.org/10.3390/molecules26103057
Chicago/Turabian StyleBuzun, Kamila, Anna Kryshchyshyn-Dylevych, Julia Senkiv, Olexandra Roman, Andrzej Gzella, Krzysztof Bielawski, Anna Bielawska, and Roman Lesyk. 2021. "Synthesis and Anticancer Activity Evaluation of 5-[2-Chloro-3-(4-nitrophenyl)-2-propenylidene]-4-thiazolidinones" Molecules 26, no. 10: 3057. https://doi.org/10.3390/molecules26103057