80841-47-0
Chemical Structure
Asulacrine
Synonym(s): CI-921; NSC 343499
- CAS No.: 80841-47-0
- Formula:C24H24N4O4S
- Molecular Weight:464.54
InChIKey: TWHSQQYCDVSBRK-UHFFFAOYSA-N
SMILES: O=C(C1=CC=CC2=C1N=C3C(C=CC=C3C)=C2NC4=CC=C(NS(=O)(C)=O)C=C4OC)NC
Biological Activity: Asulacrine (CI-921) is an orally active DNA intercalating topoisomerase II inhibitor. Asulacrine binds to DNA via intercalation, with its acridine chromophore intercalated between base pairs and substituents located in the major/minor grooves, which stabilizes DNA against acid denaturation. Asulacrine acts as a cell cycle inhibitor, disruptor, and arrest inducer, slowing cell progression in late S/G2 phase, causing G2 phase arrest and inducing unbalanced growth. Asulacrine inhibits cell growth, clonogenicity, and colony formation, and leads to histological destruction of tumor cells. Compared to cells in exponential growth phase, Asulacrine exhibits lower toxicity to quiescent cells; its activity depends on cationic properties, and it has better water solubility and metabolic stability. Asulacrine can be used in research related to leukemia, lung cancer, colon cancer, breast cancer, melanoma, adriamycin-resistant mammary adenocarcinoma, and mouse solid tumors[1][2][3][4][5][6].
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Asulacrine | Asulacrine (CI-921) is an orally active DNA intercalating topoisomerase II inhibitor. Asulacrine binds to DNA via intercalation, with its acridine chromophore intercalated between base pairs and substituents located in the major/minor grooves, which stabilizes DNA against acid denaturation. Asulacrine acts as a cell cycle inhibitor, disruptor, and arrest inducer, slowing cell progression in late S/G2 phase, causing G2 phase arrest and inducing unbalanced growth. Asulacrine inhibits cell growth, clonogenicity, and colony formation, and leads to histological destruction of tumor cells. Compared to cells in exponential growth phase, Asulacrine exhibits lower toxicity to quiescent cells; its activity depends on cationic properties, and it has better water solubility and metabolic stability. Asulacrine can be used in research related to leukemia, lung cancer, colon cancer, breast cancer, melanoma, adriamycin-resistant mammary adenocarcinoma, and mouse solid tumors. | |||||||||||||||||||||
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- [1]. Hays SJ, Huang CC. Deuterium, tritium, and carbon-14 labeling of 9-[[2-methoxy-4-[(methylsulfonyl)amino]phenyl]amino]-N,5-dimethylacridinecarboxamide (CI-921), a new antitumor agent. J Labelled Comp Radiopharm. 1984;21(6):575-586.
- [2]. Gellerman G. Recent Synthetic Approaches to Anti-cancer 9-Anilinoacridines. A Review. Org Prep Proced Int. 2012;44(3):187-221.
- [3]. Traganos F, Bueti C, Darzynkiewicz Z, Melamed MR. Effects of a New Amsacrine Derivative, N-5-Dimethyl-9-(2-methoxy-4-methylsulfonylamino)phenylamino-4-acridinecarboxamide, on Cultured Mammalian Cells. Cancer Res. 1987;47(2):424-432.
- [4]. Baguley BC, et al. Effects of CI-921, an analogue of amsacrine, on advanced Lewis lung tumours in mice: relevance to clinical trials. European journal of cancer & clinical oncology. 1988 Feb;24(2):211-8. [Content Brief]
- [5]. Baguley BC, et al. Schedule dependence of activity of the amsacrine analogue CI-921 towards P388 leukaemia and Lewis lung carcinoma. European journal of cancer & clinical oncology. 1985 Nov;21(11):1337-41. [Content Brief]
- [6]. Paxton JW, et al. The clinical pharmacokinetics of N-5-dimethyl-9-[(2-methoxy-4-methyl-sulfonylamino)phenylamino]-4 -acridinecarboxamide (CI-921) in a phase 1 trial. Cancer chemotherapy and pharmacology. 1988;22(3):235-40. [Content Brief]
Keywords
