Novel antitumor artemisinin derivatives targeting G1 phase of the cell cycle
Modification of artemisinin structure led us to the discovery of a novel class of antitumor compounds. These artemisinin derivatives containing cyano and aryl groups showed potent antiproliferative effect in vitro against P388 and A549 cells. This activity was reflected in P388 murine leukemia by an...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 11; no. 1; pp. 5 - 8 |
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| Main Authors | , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Oxford
Elsevier Ltd
08.01.2001
Elsevier |
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| Abstract | Modification of artemisinin structure led us to the discovery of a novel class of antitumor compounds. These artemisinin derivatives containing cyano and aryl groups showed potent antiproliferative effect in vitro against P388 and A549 cells. This activity was reflected in P388 murine leukemia by an accumulation of cells in G1 phase, and induction of apoptosis. |
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| AbstractList | Modification of artemisinin structure led us to the discovery of a novel class of antitumor compounds. These artemisinin derivatives containing cyano and aryl groups showed potent antiproliferative effect in vitro against P388 and A549 cells. This activity was reflected in P388 murine leukemia by an accumulation of cells in G1 phase, and induction of apoptosis. |
| Author | Atassi, Ghanem Li, Ying Yang, Wei-Yi Léonce, Stéphane Caignard, Daniel-Henri Xiao, Dong Shan, Feng Renard, Pierre Ding, Jian Wu, Jin-Ming Wu, Guang-Shao |
| Author_xml | – sequence: 1 givenname: Ying surname: Li fullname: Li, Ying email: yli@mail.shcnc.ac.cn organization: Department of Synthetic Chemistry, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China – sequence: 2 givenname: Feng surname: Shan fullname: Shan, Feng organization: Department of Synthetic Chemistry, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China – sequence: 3 givenname: Jin-Ming surname: Wu fullname: Wu, Jin-Ming organization: Department of Synthetic Chemistry, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China – sequence: 4 givenname: Guang-Shao surname: Wu fullname: Wu, Guang-Shao organization: Department of Synthetic Chemistry, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China – sequence: 5 givenname: Jian surname: Ding fullname: Ding, Jian organization: Department of Pharmacology, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China – sequence: 6 givenname: Dong surname: Xiao fullname: Xiao, Dong organization: Department of Pharmacology, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China – sequence: 7 givenname: Wei-Yi surname: Yang fullname: Yang, Wei-Yi organization: Department of Pharmacology, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China – sequence: 8 givenname: Ghanem surname: Atassi fullname: Atassi, Ghanem organization: Institut de Recherche Servier, Suresnes, France – sequence: 9 givenname: Stéphane surname: Léonce fullname: Léonce, Stéphane organization: Institut de Recherche Servier, Suresnes, France – sequence: 10 givenname: Daniel-Henri surname: Caignard fullname: Caignard, Daniel-Henri organization: ADIR ET COMPAGNIE, Courbevoie, France – sequence: 11 givenname: Pierre surname: Renard fullname: Renard, Pierre organization: ADIR ET COMPAGNIE, Courbevoie, France |
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| Cites_doi | 10.1016/0960-894X(95)00297-7 10.1055/s-2006-957438 10.1021/np9605495 10.1016/S0968-0896(97)00079-5 10.1111/j.2042-7158.1997.tb06080.x 10.1021/jm990363d 10.1016/S0960-894X(97)00169-8 10.1128/MR.60.2.301-315.1996 10.1128/AAC.34.10.1961 10.1055/s-2006-957533 10.1007/BF00210788 10.1128/AAC.35.6.1225 10.1021/np50096a007 |
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| Keywords | Antineoplastic agent Endoperoxide Human Terpenoid Nitrile Lung P388-Leukemia Cytotoxicity In vitro Biological activity Peracetal G1 Phase Cell line Cell death Sesquiterpenes Cell cycle Benzenic compound Chemical synthesis Apoptosis |
| Language | English |
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| References | C 69.15, H 7.32, N 3.51. Found: C 68.85, H 7.42, N 3.18. 3.40 673. (d) Liu, C.-M.; Qu-Yang, K. 1.43 (3H, s, 4-CH C 59.74, H 6.10, N 3.03. Found: C 59.85, H 5.78, N 3.31. 7.48 1225. (b) Ou-Yang, K.; Krug, E. C.; Marr, J. J.; Berens, R. L. Liang, Li (BIB7) 1996; 6 Tan, Zheng, Tang (BIB13) 1998; 64 Hz, aromatic H), 7.57 (2H, d 6.37 1.47 (3H, s, 4-CH 1961. (c) Chen, Y. T.; Ma, L.; Mei, Q.; Tang, Y.; Liao, X.-G. Anal calcd for (C Hz, aromatic H), 7.55 (2H, d The X-ray crystallographic data have been deposited at the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK. mp 122–122.5 3.43 6.32 0.95 (3H, d 0.96 (3H, d Zhang, Yang, Pan (BIB15) 1998; 29 Data for mp 128–129 4.06 Woerdenbag, Moskal, Pras, Malingre, El-Feraly, Kampinga, Konings (BIB5) 1993; 56 June, ElSohly, MeChesney (BIB4) 1990; 56 0.91 (3H, d Leonce, Perez, Casablanca-Pignede, Anstett, Bisagni, Pierre, Atassi (BIB21) 1996; 14 6.02 H NMR (400 Yang, Li, Shi, Yang, Wu (BIB6) 1995; 5 C 69.15, H 7.32, N 3.51. Found: C 68.86, H 7.35, N 3.33. Meshnick, Taylor, Kamchonwongpaisan (BIB1) 1996; 60 1.00 (3H, d , Beekman (BIB10) 1997; 49 BrNO Hz, aromatic H). IR (KBr): 1592.9, 1486.9, 1103.1, 1035.6, 954.6, 879.4 Hz, 12-H), 5.34 (1H, s, 16-H), 5.47 (1H, s, 5-H), 7.31 (2H, d 4.79 (1H, d MHz), δ: 0.87 (3H, d (a) Merali, S.; Meshnick, S. R. Venugopalan, B.; Bapat, C. P.; Karnik, P. J.; Lal, B.; Chatterjee, D. K.; Iyer, S. N.; Rupp, R. H. Eur. Patent EP 362730, 1989 MHz), δ: 0.85 (3H, d Yang, Pan, Liang, Zhang (BIB12) 1997; 16 Hz, 12-H), 5.28 (1H, s, 16-H), 5.68 (1H, s, 5-H), 7.44 (5H, m, aromatic H). IR (KBr): 1457.9, 1103.1, 875.5 Wu, Li (BIB2) 1995; 5 264 (in Chinese). 3.62 1.44 (3H, s, 4-CH NO Beekman, Wierenga, Woerdenbag, Uden, Pras, Konings, El-Feraly, Gala, Wikstrom (BIB14) 1998; 64 7.25 7.27 6.59 MHz), δ: 0.90 (3H, d H Hz, 11-CH 8.30 mp 135–137 C. Anal. calcd for (C 3.66 Hz, 12-H), 5.46 (1H, s, 16-H), 5.58 (1H, s, 5-H), 7.32 (2H, d 6.10 Posner, Ploypradith, Parker, O'Dowd, Woo, Northrop, Krasavin, Dolan, Kensler, Xie, Shapiro (BIB16) 1999; 42 C 57.75, H 5.90, N 2.93. Found: C 57.80, H 6.07, N 2.85. 1.01 (3H, d 5.24 (1H, d 5.22 (1H, d Jung (BIB8) 1997; 7 8.48 8.49 8.46 7.36 C 57.75, H 5.90, N 2.93. Found: C 57.80, H 5.89, N 2.96. Posner (BIB9) 1997; 7 mp 98–100 Hz, aromatic H). IR (KBr): 1592.9, 1488.8, 1375.0, 1101.2, 1031.7, 1010.5, 954.6, 875.5 8.40 Hz, 10-CH mp 144–145 cm 4.81 (1H, d Beekman, Barentsen, Woerdenbag, Uden, Pras, Konings, El-Feraly, Galal, Wikstrom (BIB11) 1997; 60 7.32 4.78 (1H, d 86. Hz, aromatic H). IR (KBr): 1592.9, 1486.9, 1394.3, 1211.1, 1103.0, 929.8, 867.8 Hz, 12-H), 5.50 (1H, s, 16-H), 5.60 (1H, s, 5-H), 7.42 (5H, m, aromatic H). IR (KBr): 1452.2, 1101.2, 877.5 MHz), δ: 0.84 (3H, d MHz), δ: 0.88 (3H, d Hz, aromatic H), 7.54 (2H, d Hz, 12-H), 5.25 (1H, s, 16-H), 5.63 (1H, s, 5-H), 7.33 (2H, d Yang (10.1016/S0960-894X(00)00578-3_BIB6) 1995; 5 cr-split#-10.1016/S0960-894X(00)00578-3_BIB3.1 Beekman (10.1016/S0960-894X(00)00578-3_BIB10) 1997; 49 cr-split#-10.1016/S0960-894X(00)00578-3_BIB3.2 cr-split#-10.1016/S0960-894X(00)00578-3_BIB3.3 Beekman (10.1016/S0960-894X(00)00578-3_BIB14) 1998; 64 10.1016/S0960-894X(00)00578-3_BIB19 10.1016/S0960-894X(00)00578-3_BIB18 Tan (10.1016/S0960-894X(00)00578-3_BIB13) 1998; 64 10.1016/S0960-894X(00)00578-3_BIB17 Yang (10.1016/S0960-894X(00)00578-3_BIB12) 1997; 16 June (10.1016/S0960-894X(00)00578-3_BIB4) 1990; 56 Meshnick (10.1016/S0960-894X(00)00578-3_BIB1) 1996; 60 Leonce (10.1016/S0960-894X(00)00578-3_BIB21) 1996; 14 Woerdenbag (10.1016/S0960-894X(00)00578-3_BIB5) 1993; 56 Liang (10.1016/S0960-894X(00)00578-3_BIB7) 1996; 6 Posner (10.1016/S0960-894X(00)00578-3_BIB16) 1999; 42 Beekman (10.1016/S0960-894X(00)00578-3_BIB11) 1997; 60 Posner (10.1016/S0960-894X(00)00578-3_BIB9) 1997; 7 Zhang (10.1016/S0960-894X(00)00578-3_BIB15) 1998; 29 cr-split#-10.1016/S0960-894X(00)00578-3_BIB3.4 Wu (10.1016/S0960-894X(00)00578-3_BIB2) 1995; 5 Jung (10.1016/S0960-894X(00)00578-3_BIB8) 1997; 7 10.1016/S0960-894X(00)00578-3_BIB20 |
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| Snippet | Modification of artemisinin structure led us to the discovery of a novel class of antitumor compounds. These artemisinin derivatives containing cyano and aryl... |
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| SubjectTerms | Animals Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Apoptosis - drug effects Artemisinins Biological and medical sciences Cell Division - drug effects G1 Phase - drug effects General aspects Humans Inhibitory Concentration 50 Medical sciences Mice Models, Molecular Molecular Structure Pharmacology. Drug treatments Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Sesquiterpenes - pharmacology Sesquiterpenes - toxicity Tumor Cells, Cultured |
| Title | Novel antitumor artemisinin derivatives targeting G1 phase of the cell cycle |
| URI | https://dx.doi.org/10.1016/S0960-894X(00)00578-3 https://www.ncbi.nlm.nih.gov/pubmed/11140731 |
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