Design and synthesis of threading intercalators to target DNA
Threading intercalators are high affinity DNA binding agents that bind by inserting a chromophore into the duplex and locating one group in each groove. The first threading intercalators that can be conjugated to acids, sulfonic acids and peptides to target them to duplex DNA are described, based up...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 20; no. 23; pp. 6956 - 6959 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Amsterdam
Elsevier Ltd
01.12.2010
Elsevier |
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| Abstract | Threading intercalators are high affinity DNA binding agents that bind by inserting a chromophore into the duplex and locating one group in each groove. The first threading intercalators that can be conjugated to acids, sulfonic acids and peptides to target them to duplex DNA are described, based upon the well studied acridine-3- or 4-carboxamides. Cellular uptake of the parent acridine is rapid and it can be visualized in the nucleus of cells. Both the parent compounds and their conjugates maintain antitumor activity. |
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| AbstractList | Threading intercalators are high affinity DNA binding agents that bind by inserting a chromophore into the duplex and locating one group in each groove. The first threading intercalators that can be conjugated to acids, sulfonic acids and peptides to target them to duplex DNA are described, based upon the well studied acridine-3- or 4-carboxamides. Cellular uptake of the parent acridine is rapid and it can be visualized in the nucleus of cells. Both the parent compounds and their conjugates maintain antitumor activity. Threading intercalators are high affinity DNA binding agents that bind by inserting a chromophore into the duplex and locating one group in each groove. The first threading intercalators that can be conjugated to acids, sulfonic acids and peptides to target them to duplex DNA are described, based upon the well studied acridine-3- or 4-carboxamides. Cellular uptake of the parent acridine is rapid and it can be visualized in the nucleus of cells. Both the parent compounds and their conjugates maintain antitumor activity.Threading intercalators are high affinity DNA binding agents that bind by inserting a chromophore into the duplex and locating one group in each groove. The first threading intercalators that can be conjugated to acids, sulfonic acids and peptides to target them to duplex DNA are described, based upon the well studied acridine-3- or 4-carboxamides. Cellular uptake of the parent acridine is rapid and it can be visualized in the nucleus of cells. Both the parent compounds and their conjugates maintain antitumor activity. |
| Author | Mueller, Anja Searcey, Mark O’Connell, Maria A. Gulam, Rosul Howell, Lesley A. |
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| Cites_doi | 10.1021/jm800900g 10.1021/ja036685v 10.1021/ol005809v 10.1016/S0968-0896(01)00262-0 10.1021/jm701228e 10.1016/j.bmc.2006.07.004 10.1021/bi9528098 10.1002/cmdc.200700229 10.1016/j.bmc.2006.06.007 10.1093/nar/gkl930 10.1021/cb600463w 10.1042/bj1570721 10.1016/j.bmcl.2009.08.070 |
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| Keywords | Intercalator Acridine DNA Human Promyelocytic leukemia Intercalating agent Peptides Acridine derivatives Cytotoxicity In vitro Biological activity HL60 cell line Octapeptide Cell line Carboxamide Conjugated compound Chemical synthesis Tumor cell |
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| SubjectTerms | Acridine Acridines - chemistry Acridines - pharmacology Animals Antineoplastic agents Antineoplastic Agents - chemistry Antitumor activity Biological and medical sciences Cell Line, Tumor DNA DNA - antagonists & inhibitors DNA - metabolism Drug Design General aspects Humans Intercalating Agents - chemical synthesis Intercalating Agents - pharmacology Intercalator Medical sciences Nucleic Acid Conformation Pharmacology. Drug treatments |
| Title | Design and synthesis of threading intercalators to target DNA |
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