Strategy for Imidazotetrazine Prodrugs with Anticancer Activity Independent of MGMT and MMR
The imidazotetrazine ring is an acid-stable precursor and prodrug of highly reactive alkyl diazonium ions. We have shown that this reactivity can be managed productively in an aqueous system for the generation of aziridinium ions with 96% efficiency. The new compounds are potent DNA alkylators and h...
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| Published in | ACS medicinal chemistry letters Vol. 3; no. 12; pp. 965 - 968 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
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American Chemical Society
13.12.2012
Amer Chemical Soc |
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| Abstract | The imidazotetrazine ring is an acid-stable precursor and prodrug of highly reactive alkyl diazonium ions. We have shown that this reactivity can be managed productively in an aqueous system for the generation of aziridinium ions with 96% efficiency. The new compounds are potent DNA alkylators and have antitumor activity independent of the O6-methylguanine-DNA methyltransferase and DNA mismatch repair constraints that limit the use of Temozolomide. |
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| AbstractList | The imidazotetrazine ring is an acid-stable precursor and prodrug of highly reactive alkyl diazonium ions. We have shown that this reactivity can be managed productively in an aqueous system for the generation of aziridinium ions with 96% efficiency. The new compounds are potent DNA alkylators and have antitumor activity independent of the O6-methylguanine-DNA methyltransferase and DNA mismatch repair constraints that limit the use of Temozolomide. The imidazotetrazine ring is an acid-stable precursor and prodrug of highly reactive alkyl diazonium ions. We have shown that this reactivity can be managed productively in an aqueous system for the generation of aziridinium ions with 96% efficiency. The new compounds are potent DNA alkylators and have antitumor activity independent of the O6-methylguanine-DNA methyltransferase and DNA mismatch repair constraints that limit the use of Temozolomide.The imidazotetrazine ring is an acid-stable precursor and prodrug of highly reactive alkyl diazonium ions. We have shown that this reactivity can be managed productively in an aqueous system for the generation of aziridinium ions with 96% efficiency. The new compounds are potent DNA alkylators and have antitumor activity independent of the O6-methylguanine-DNA methyltransferase and DNA mismatch repair constraints that limit the use of Temozolomide. The imidazotetrazine ring is an acid-stable precursor and prodrug of highly reactive alkyl diazonium ions. We have shown that this reactivity can be managed productively in an aqueous system for the generation of aziridinium ions with 96% efficiency. The new compounds are potent DNA alkylators and have antitumor activity independent of the O 6-methylguanine-DNA methyltransferase and DNA mismatch repair constraints that limit the use of Temozolomide. |
| Author | Li, Li Wheelhouse, Richard T Kiakos, Konstantinos Hartley, John A Phillips, Roger M Karodia, Nazira Garelnabi, Elrashied A. E Pletsas, Dimitrios |
| AuthorAffiliation | School of Pharmacy Institute of Cancer Therapeutics Chemical and Forensic Sciences UCL Cancer Institute University of Bradford |
| AuthorAffiliation_xml | – name: Institute of Cancer Therapeutics – name: Chemical and Forensic Sciences – name: UCL Cancer Institute – name: School of Pharmacy – name: University of Bradford |
| Author_xml | – sequence: 1 givenname: Elrashied A. E surname: Garelnabi fullname: Garelnabi, Elrashied A. E – sequence: 2 givenname: Dimitrios surname: Pletsas fullname: Pletsas, Dimitrios – sequence: 3 givenname: Li surname: Li fullname: Li, Li – sequence: 4 givenname: Konstantinos surname: Kiakos fullname: Kiakos, Konstantinos – sequence: 5 givenname: Nazira surname: Karodia fullname: Karodia, Nazira – sequence: 6 givenname: John A surname: Hartley fullname: Hartley, John A – sequence: 7 givenname: Roger M surname: Phillips fullname: Phillips, Roger M – sequence: 8 givenname: Richard T surname: Wheelhouse fullname: Wheelhouse, Richard T email: r.t.wheelhouse@brad.ac.uk |
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| Keywords | Imidazotetrazine aziridinium cancer Temozolomide 13C NMR DNA ANTITUMOR DRUG TEMOZOLOMIDE DECOMPOSITION C-13 NMR |
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Part 36. 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| Snippet | The imidazotetrazine ring is an acid-stable precursor and prodrug of highly reactive alkyl diazonium ions. We have shown that this reactivity can be managed... The imidazotetrazine ring is an acid-stable precursor and prodrug of highly reactive alkyl diazonium ions. We have shown that this reactivity can be managed... |
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| Title | Strategy for Imidazotetrazine Prodrugs with Anticancer Activity Independent of MGMT and MMR |
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