Novel N-quaternary coumarin-3-yl-imidazo[1,2-a]pyridines as fluorescent hybrids: Their synthesis and biological evaluation in cancer cells
Hybrid coumarin-3-yl-imidazo[1,2-a]pyridines were used to synthesize novel derivatives of quaternary salts 5a-c and 6a,b, employing ethyl iodide and benzyl bromide as alkylating agents. The molecular patterns of Total Polar Surface Area (TPSA) coincide with substituent polarity at positions 6 or 7,...
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Elsevier
2025-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715624006556 |
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| author | Karla Armendariz-Barrientos Luis A. Pérez Selene Lagunas-Rivera Yolanda Alcaraz-Contreras Marco A. García-Revilla Heriberto Prado-Garcia Rocío García-Becerra Miguel A. Vazquez |
| author_facet | Karla Armendariz-Barrientos Luis A. Pérez Selene Lagunas-Rivera Yolanda Alcaraz-Contreras Marco A. García-Revilla Heriberto Prado-Garcia Rocío García-Becerra Miguel A. Vazquez |
| author_sort | Karla Armendariz-Barrientos |
| collection | DOAJ |
| description | Hybrid coumarin-3-yl-imidazo[1,2-a]pyridines were used to synthesize novel derivatives of quaternary salts 5a-c and 6a,b, employing ethyl iodide and benzyl bromide as alkylating agents. The molecular patterns of Total Polar Surface Area (TPSA) coincide with substituent polarity at positions 6 or 7, along with the substituent at the quaternary N. Notably, most polar molecules contain an amino group at position 7, followed by those substituted with −OMe at position 6. Conversely, molecules lacking substituents are the least polar. Despite existing as salts, the polarity of the compounds does not experience a substantial increase. Nonetheless, solubility experiences a notable decrease, particularly for the 6a-c series, due to the potent hydrophobic effect of the benzyl substituent at the N position. A similar phenomenon is observed with the ethyl substituent in the 5a-c series, albeit with a less pronounced hydrophobic impact. To assess the effect of the quaternary hybrid coumarin-3-yl-imidazo[1,2-a]pyridines on proliferation, both breast (MDA-MB-231) and prostate (PC3) cancer cell lines were utilized. The biological assessment of these cancer cell lines demonstrated that compounds 4a, 4c, and 5c exhibit noteworthy antiproliferative effects on MDA-MB-231 (Inhibitory concentration at 50 % (IC50) values of 2.27 µM, 3.76 µM, and 0.113 µM, respectively) and PC3 (IC50 values of 1.03 µM, 0.527 µM, and 0.888 µM, respectively). Furthermore, these same structures demonstrated substantial fluorescence emissions localized within the cytoplasm. Additionally, compounds decreased the G2/M phase of the cell cycle and increased the SubG1 phase. These findings suggest that these novel hybrids have promising applications in cancer treatment. |
| format | Article |
| id | doaj-art-4318586b54af4a8289bbe538c08bcd42 |
| institution | Kabale University |
| issn | 2211-7156 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Elsevier |
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| series | Results in Chemistry |
| spelling | doaj-art-4318586b54af4a8289bbe538c08bcd422025-01-29T05:00:41ZengElsevierResults in Chemistry2211-71562025-01-0113101959Novel N-quaternary coumarin-3-yl-imidazo[1,2-a]pyridines as fluorescent hybrids: Their synthesis and biological evaluation in cancer cellsKarla Armendariz-Barrientos0Luis A. Pérez1Selene Lagunas-Rivera2Yolanda Alcaraz-Contreras3Marco A. García-Revilla4Heriberto Prado-Garcia5Rocío García-Becerra6Miguel A. Vazquez7Departamento de Química, Universidad de Guanajuato, Guanajuato, Gto., 36050, México; Departamento de Biología Molecular y Biotecnología, Instituto de Investigaciones Biomédicas, Universidad Nacional Autónoma de México, 04510 Ciudad de México, MéxicoDepartamento de Química, Universidad de Guanajuato, Guanajuato, Gto., 36050, MéxicoInvestigadora por México-CONAHCyT, Departamento de Química, DCNyE Universidad de Guanajuato, Guanajuato, Gto., 36050, MéxicoDepartamento de Farmacia, Universidad de Guanajuato, Guanajuato, Gto., 36050, MéxicoDepartamento de Química, Universidad de Guanajuato, Guanajuato, Gto., 36050, MéxicoLaboratorio de Onco-Inmunobiología, Departamento de Enfermedades Crónico-Degenerativas. Instituto Nacional de Enfermedades Respiratorias Ismael Cosío Villegas, Calzada de Tlalpan 4502, Belisario Domínguez Sección XVI, Tlalpan 14080, Ciudad de México, MéxicoDepartamento de Biología Molecular y Biotecnología, Instituto de Investigaciones Biomédicas, Universidad Nacional Autónoma de México, 04510 Ciudad de México, México; Programa de Investigación Cáncer de Mama, Instituto de Investigaciones Biomédicas, Universidad Nacional Autónoma de México, 04510, Ciudad de México, México; Corresponding autor.Departamento de Química, Universidad de Guanajuato, Guanajuato, Gto., 36050, México; Corresponding autor.Hybrid coumarin-3-yl-imidazo[1,2-a]pyridines were used to synthesize novel derivatives of quaternary salts 5a-c and 6a,b, employing ethyl iodide and benzyl bromide as alkylating agents. The molecular patterns of Total Polar Surface Area (TPSA) coincide with substituent polarity at positions 6 or 7, along with the substituent at the quaternary N. Notably, most polar molecules contain an amino group at position 7, followed by those substituted with −OMe at position 6. Conversely, molecules lacking substituents are the least polar. Despite existing as salts, the polarity of the compounds does not experience a substantial increase. Nonetheless, solubility experiences a notable decrease, particularly for the 6a-c series, due to the potent hydrophobic effect of the benzyl substituent at the N position. A similar phenomenon is observed with the ethyl substituent in the 5a-c series, albeit with a less pronounced hydrophobic impact. To assess the effect of the quaternary hybrid coumarin-3-yl-imidazo[1,2-a]pyridines on proliferation, both breast (MDA-MB-231) and prostate (PC3) cancer cell lines were utilized. The biological assessment of these cancer cell lines demonstrated that compounds 4a, 4c, and 5c exhibit noteworthy antiproliferative effects on MDA-MB-231 (Inhibitory concentration at 50 % (IC50) values of 2.27 µM, 3.76 µM, and 0.113 µM, respectively) and PC3 (IC50 values of 1.03 µM, 0.527 µM, and 0.888 µM, respectively). Furthermore, these same structures demonstrated substantial fluorescence emissions localized within the cytoplasm. Additionally, compounds decreased the G2/M phase of the cell cycle and increased the SubG1 phase. These findings suggest that these novel hybrids have promising applications in cancer treatment.http://www.sciencedirect.com/science/article/pii/S2211715624006556N-quaternary coumarin-3-yl-imidazo[12-a]pyridines hybridsChromophoresFluorescent detectionAntiproliferative activityADMED analysis |
| spellingShingle | Karla Armendariz-Barrientos Luis A. Pérez Selene Lagunas-Rivera Yolanda Alcaraz-Contreras Marco A. García-Revilla Heriberto Prado-Garcia Rocío García-Becerra Miguel A. Vazquez Novel N-quaternary coumarin-3-yl-imidazo[1,2-a]pyridines as fluorescent hybrids: Their synthesis and biological evaluation in cancer cells Results in Chemistry N-quaternary coumarin-3-yl-imidazo[1 2-a]pyridines hybrids Chromophores Fluorescent detection Antiproliferative activity ADMED analysis |
| title | Novel N-quaternary coumarin-3-yl-imidazo[1,2-a]pyridines as fluorescent hybrids: Their synthesis and biological evaluation in cancer cells |
| title_full | Novel N-quaternary coumarin-3-yl-imidazo[1,2-a]pyridines as fluorescent hybrids: Their synthesis and biological evaluation in cancer cells |
| title_fullStr | Novel N-quaternary coumarin-3-yl-imidazo[1,2-a]pyridines as fluorescent hybrids: Their synthesis and biological evaluation in cancer cells |
| title_full_unstemmed | Novel N-quaternary coumarin-3-yl-imidazo[1,2-a]pyridines as fluorescent hybrids: Their synthesis and biological evaluation in cancer cells |
| title_short | Novel N-quaternary coumarin-3-yl-imidazo[1,2-a]pyridines as fluorescent hybrids: Their synthesis and biological evaluation in cancer cells |
| title_sort | novel n quaternary coumarin 3 yl imidazo 1 2 a pyridines as fluorescent hybrids their synthesis and biological evaluation in cancer cells |
| topic | N-quaternary coumarin-3-yl-imidazo[1 2-a]pyridines hybrids Chromophores Fluorescent detection Antiproliferative activity ADMED analysis |
| url | http://www.sciencedirect.com/science/article/pii/S2211715624006556 |
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