Synthesis and in vitro cytotoxicity of 9-anilinoacridines bearing N-mustard residue on both anilino and acridine rings Journal Article
| Authors: | Chen, C. H.; Lin, Y. W.; Zhang, X.; Chou, T. C.; Tsai, T. J.; Kapuriya, N.; Kakadiya, R.; Su, T. L. |
| Article Title: | Synthesis and in vitro cytotoxicity of 9-anilinoacridines bearing N-mustard residue on both anilino and acridine rings |
| Abstract: | A series of 9-anilinoacridines having an alkylating N-mustard pharmacophore on both anilino (C-3′ or C-4′) and acridine (C-4) rings with O-ethyl (O-C<sub>2</sub>) or O-butyl (O-C<sub>4</sub>) spacer were synthesized to evaluate their cytotoxicity against human lymphoblastic leukemia (CCRF-CEM) cell growth in vitro. It was revealed that these conjugates exhibited significant in vitro cytotoxicity. Among these agents, compound 13 was the most cytotoxic with IC<sub>50</sub> value of 1.3 nM and is as potent as taxol (IC<sub>50</sub> = 1.1 nM). The structure-activity relationship study showed that the length of the spacer and the position of the substituent do affect their cytotoxicity. © 2008 Elsevier Masson SAS. All rights reserved. |
| Keywords: | controlled study; unclassified drug; human cell; antineoplastic agents; paclitaxel; antineoplastic agent; cell proliferation; cell growth; drug potency; drug structure; in vitro study; cell line, tumor; drug synthesis; structure activity relation; precursor cell lymphoblastic leukemia-lymphoma; 9-anilinoacridines; cytotoxic; dna-alkylating agents; nitrogen mustards; 3 (9 acridinylamino) 5 hydroxymethylaniline; 9 anilinoacridine derivative; [4 [2 [bis(2 chloroethyl)amino]butoxy]acridin 9 yl] [4 [2 [bis(2 chloroethyl)amino]ethoxy]phenyl]amine; [4 [2 [bis(2 chloroethyl)amino]ethoxy]acridin 9 yl] [3 [2 [bis(2 chloroethyl)amino]butoxy]phenyl]amine; [4 [2 [bis(2 chloroethyl)amino]ethoxy]acridin 9 yl] [3 [2 [bis(2 chloroethyl)amino]ethoxy]phenyl]amine; [4 [2 [bis(2 chloroethyl)amino]ethoxy]acridin 9 yl] [4 [2 [bis(2 chloroethyl)amino]butoxy]phenyl]amine; [4 [2 [bis(2 chloroethyl)amino]ethoxy]acridin 9 yl] [4 [2 [bis(2 chloroethyl)amino]ethoxy]phenyl]amine; alkylation; drug cytotoxicity; lymphatic leukemia; pharmacophore; amsacrine; aniline compounds; mustard compounds |
| Journal Title: | European Journal of Medicinal Chemistry |
| Volume: | 44 |
| Issue: | 7 |
| ISSN: | 0223-5234 |
| Publisher: | Elsevier Inc. |
| Date Published: | 2009-07-01 |
| Start Page: | 3056 |
| End Page: | 3059 |
| Language: | English |
| DOI: | 10.1016/j.ejmech.2008.07.016 |
| PUBMED: | 18752869 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 4" - "Export Date: 30 November 2010" - "CODEN: EJMCA" - "Source: Scopus" |
Altmetric
Citation Impact
BMJ Impact Analytics
Related MSK Work