Differential effect of heterocyclic d-ribofuranoside derivatives on human prostate cancer cell viability and cell cycle progression
New d-ribofuranoside derivatives containing two five membered heterocycles, isoxazole and triazole or two triazole rings, were synthesized. The final products as well as the synthetic precursors were physically and spectroscopically characterized. These new diheterocyclic derivatives together with o...
Guardado en:
| Autores principales: | , , , |
|---|---|
| Publicado: |
2014
|
| Materias: | |
| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07533322_v68_n7_p847_Gueron http://hdl.handle.net/20.500.12110/paper_07533322_v68_n7_p847_Gueron |
| Aporte de: |
| id |
paper:paper_07533322_v68_n7_p847_Gueron |
|---|---|
| record_format |
dspace |
| spelling |
paper:paper_07533322_v68_n7_p847_Gueron2023-06-08T15:45:43Z Differential effect of heterocyclic d-ribofuranoside derivatives on human prostate cancer cell viability and cell cycle progression Gueron, Geraldine Vázquez, Elba Susana Fascio, Mirta Liliana D'Accorso, Norma Beatriz D-Ribose Isoxazole PC3 cell line Prostate cancer Triazole 2,3 o cyclopentylidene 5 tosyl beta dextro ribofuranoside 2,3 o cyclopentylidene beta dextro ribofuranoside 2,3 o isopropylidene 5 tosyl beta dextro ribofuranoside 2,3 o isopropylidene beta dextro ribofuranoside antineoplastic agent isoxazole derivative ribose triazole derivative unclassified drug [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 2,3 o cyclopentylidene 5 tosyl beta dextro ribofuranoside [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 2,3 o isopropylidene 5 tosyl beta dextro ribofuranoside [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o cyclopentylidene beta dextro ribofuranoside [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o isopropylidene beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 2,3 o cyclopentylidene 5 tosyl beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 2,3 o isopropylidene 5 tosyl beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o cyclopentylidene beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o isopropylidene beta dextro ribofuranoside alkene antineoplastic agent carbohydrate isoxazole derivative propylene triazole derivative apoptosis Article cancer cell cancer growth carbohydrate analysis carbon nuclear magnetic resonance cell cycle progression cell viability controlled study drug synthesis G1 phase cell cycle checkpoint G2 phase cell cycle checkpoint heteronuclear multiple bond correlation heteronuclear single quantum coherence human human cell IC50 polyacrylamide gel electrophoresis prostate cancer prostate cancer cell line protein expression cell cycle G0 phase cell survival drug effects male Prostatic Neoplasms tumor cell line Alkenes Antineoplastic Agents Carbohydrates Cell Line, Tumor Cell Survival G0 Phase G1 Phase Cell Cycle Checkpoints Humans Isoxazoles Male Prostatic Neoplasms Triazoles New d-ribofuranoside derivatives containing two five membered heterocycles, isoxazole and triazole or two triazole rings, were synthesized. The final products as well as the synthetic precursors were physically and spectroscopically characterized. These new diheterocyclic derivatives together with other d-riboside compounds were assessed for their impact on PC3 cell line viability. We found that exposure of prostate cancer cells to some of these compounds caused a significant inhibition of cell growth and a G0/G1 cell cycle arrest, which was concomitant with alterations in the expression of proteins involved in cell cycle progression. Furthermore, the inhibitory activity was improved in di-heterocycles when the carbohydrate moiety was protected with a cyclopentylidene group compared to the isopropylidene analogues. © 2014 Elsevier Masson SAS. Fil:Gueron, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Vazquez, E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Fascio, M.L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:D'Accorso, N.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2014 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07533322_v68_n7_p847_Gueron http://hdl.handle.net/20.500.12110/paper_07533322_v68_n7_p847_Gueron |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
D-Ribose Isoxazole PC3 cell line Prostate cancer Triazole 2,3 o cyclopentylidene 5 tosyl beta dextro ribofuranoside 2,3 o cyclopentylidene beta dextro ribofuranoside 2,3 o isopropylidene 5 tosyl beta dextro ribofuranoside 2,3 o isopropylidene beta dextro ribofuranoside antineoplastic agent isoxazole derivative ribose triazole derivative unclassified drug [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 2,3 o cyclopentylidene 5 tosyl beta dextro ribofuranoside [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 2,3 o isopropylidene 5 tosyl beta dextro ribofuranoside [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o cyclopentylidene beta dextro ribofuranoside [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o isopropylidene beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 2,3 o cyclopentylidene 5 tosyl beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 2,3 o isopropylidene 5 tosyl beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o cyclopentylidene beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o isopropylidene beta dextro ribofuranoside alkene antineoplastic agent carbohydrate isoxazole derivative propylene triazole derivative apoptosis Article cancer cell cancer growth carbohydrate analysis carbon nuclear magnetic resonance cell cycle progression cell viability controlled study drug synthesis G1 phase cell cycle checkpoint G2 phase cell cycle checkpoint heteronuclear multiple bond correlation heteronuclear single quantum coherence human human cell IC50 polyacrylamide gel electrophoresis prostate cancer prostate cancer cell line protein expression cell cycle G0 phase cell survival drug effects male Prostatic Neoplasms tumor cell line Alkenes Antineoplastic Agents Carbohydrates Cell Line, Tumor Cell Survival G0 Phase G1 Phase Cell Cycle Checkpoints Humans Isoxazoles Male Prostatic Neoplasms Triazoles |
| spellingShingle |
D-Ribose Isoxazole PC3 cell line Prostate cancer Triazole 2,3 o cyclopentylidene 5 tosyl beta dextro ribofuranoside 2,3 o cyclopentylidene beta dextro ribofuranoside 2,3 o isopropylidene 5 tosyl beta dextro ribofuranoside 2,3 o isopropylidene beta dextro ribofuranoside antineoplastic agent isoxazole derivative ribose triazole derivative unclassified drug [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 2,3 o cyclopentylidene 5 tosyl beta dextro ribofuranoside [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 2,3 o isopropylidene 5 tosyl beta dextro ribofuranoside [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o cyclopentylidene beta dextro ribofuranoside [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o isopropylidene beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 2,3 o cyclopentylidene 5 tosyl beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 2,3 o isopropylidene 5 tosyl beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o cyclopentylidene beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o isopropylidene beta dextro ribofuranoside alkene antineoplastic agent carbohydrate isoxazole derivative propylene triazole derivative apoptosis Article cancer cell cancer growth carbohydrate analysis carbon nuclear magnetic resonance cell cycle progression cell viability controlled study drug synthesis G1 phase cell cycle checkpoint G2 phase cell cycle checkpoint heteronuclear multiple bond correlation heteronuclear single quantum coherence human human cell IC50 polyacrylamide gel electrophoresis prostate cancer prostate cancer cell line protein expression cell cycle G0 phase cell survival drug effects male Prostatic Neoplasms tumor cell line Alkenes Antineoplastic Agents Carbohydrates Cell Line, Tumor Cell Survival G0 Phase G1 Phase Cell Cycle Checkpoints Humans Isoxazoles Male Prostatic Neoplasms Triazoles Gueron, Geraldine Vázquez, Elba Susana Fascio, Mirta Liliana D'Accorso, Norma Beatriz Differential effect of heterocyclic d-ribofuranoside derivatives on human prostate cancer cell viability and cell cycle progression |
| topic_facet |
D-Ribose Isoxazole PC3 cell line Prostate cancer Triazole 2,3 o cyclopentylidene 5 tosyl beta dextro ribofuranoside 2,3 o cyclopentylidene beta dextro ribofuranoside 2,3 o isopropylidene 5 tosyl beta dextro ribofuranoside 2,3 o isopropylidene beta dextro ribofuranoside antineoplastic agent isoxazole derivative ribose triazole derivative unclassified drug [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 2,3 o cyclopentylidene 5 tosyl beta dextro ribofuranoside [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 2,3 o isopropylidene 5 tosyl beta dextro ribofuranoside [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o cyclopentylidene beta dextro ribofuranoside [1" (3,4,5 trimethoxyphenyl) triazol 4" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o isopropylidene beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 2,3 o cyclopentylidene 5 tosyl beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 2,3 o isopropylidene 5 tosyl beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o cyclopentylidene beta dextro ribofuranoside [3" (3,4,5 trimethoxyphenyl) isoxazol 5" yl]methyl 5 deoxy 5 (1,2,4, triazol 3 yl) 2,3 o isopropylidene beta dextro ribofuranoside alkene antineoplastic agent carbohydrate isoxazole derivative propylene triazole derivative apoptosis Article cancer cell cancer growth carbohydrate analysis carbon nuclear magnetic resonance cell cycle progression cell viability controlled study drug synthesis G1 phase cell cycle checkpoint G2 phase cell cycle checkpoint heteronuclear multiple bond correlation heteronuclear single quantum coherence human human cell IC50 polyacrylamide gel electrophoresis prostate cancer prostate cancer cell line protein expression cell cycle G0 phase cell survival drug effects male Prostatic Neoplasms tumor cell line Alkenes Antineoplastic Agents Carbohydrates Cell Line, Tumor Cell Survival G0 Phase G1 Phase Cell Cycle Checkpoints Humans Isoxazoles Male Prostatic Neoplasms Triazoles |
| description |
New d-ribofuranoside derivatives containing two five membered heterocycles, isoxazole and triazole or two triazole rings, were synthesized. The final products as well as the synthetic precursors were physically and spectroscopically characterized. These new diheterocyclic derivatives together with other d-riboside compounds were assessed for their impact on PC3 cell line viability. We found that exposure of prostate cancer cells to some of these compounds caused a significant inhibition of cell growth and a G0/G1 cell cycle arrest, which was concomitant with alterations in the expression of proteins involved in cell cycle progression. Furthermore, the inhibitory activity was improved in di-heterocycles when the carbohydrate moiety was protected with a cyclopentylidene group compared to the isopropylidene analogues. © 2014 Elsevier Masson SAS. |
| author |
Gueron, Geraldine Vázquez, Elba Susana Fascio, Mirta Liliana D'Accorso, Norma Beatriz |
| author_facet |
Gueron, Geraldine Vázquez, Elba Susana Fascio, Mirta Liliana D'Accorso, Norma Beatriz |
| author_sort |
Gueron, Geraldine |
| title |
Differential effect of heterocyclic d-ribofuranoside derivatives on human prostate cancer cell viability and cell cycle progression |
| title_short |
Differential effect of heterocyclic d-ribofuranoside derivatives on human prostate cancer cell viability and cell cycle progression |
| title_full |
Differential effect of heterocyclic d-ribofuranoside derivatives on human prostate cancer cell viability and cell cycle progression |
| title_fullStr |
Differential effect of heterocyclic d-ribofuranoside derivatives on human prostate cancer cell viability and cell cycle progression |
| title_full_unstemmed |
Differential effect of heterocyclic d-ribofuranoside derivatives on human prostate cancer cell viability and cell cycle progression |
| title_sort |
differential effect of heterocyclic d-ribofuranoside derivatives on human prostate cancer cell viability and cell cycle progression |
| publishDate |
2014 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07533322_v68_n7_p847_Gueron http://hdl.handle.net/20.500.12110/paper_07533322_v68_n7_p847_Gueron |
| work_keys_str_mv |
AT guerongeraldine differentialeffectofheterocyclicdribofuranosidederivativesonhumanprostatecancercellviabilityandcellcycleprogression AT vazquezelbasusana differentialeffectofheterocyclicdribofuranosidederivativesonhumanprostatecancercellviabilityandcellcycleprogression AT fasciomirtaliliana differentialeffectofheterocyclicdribofuranosidederivativesonhumanprostatecancercellviabilityandcellcycleprogression AT daccorsonormabeatriz differentialeffectofheterocyclicdribofuranosidederivativesonhumanprostatecancercellviabilityandcellcycleprogression |
| _version_ |
1768542892901531648 |