Elinafide - CAS 162706-37-8
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Not Intended for Therapeutic Use. For research use only.
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Elinafide, an isoquinoline derivative, has been found to be a Type II DNA topoisomerase inhibitor that was once developed in anticancer studies.
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Elinafide; UNII-HL580335SI; Elinafide [INN]; 2-[2-[3-[2-(1,3-dioxobenzo[de]isoquinolin-2-yl)ethylamino]propylamino]ethyl]benzo[de]isoquinoline-1,3-dione; LU-79553
Store in a cool and dry place and at 0 - 4 °C for short term (days to weeks) or -20 °C for long term (months to years).
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In-house standard
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1.Synthesis, structural, and biological evaluation of bis-heteroarylmaleimides and bis-heterofused imides.
Ferri N1, Radice T, Antonino M, Beccalli EM, Tinelli S, Zunino F, Corsini A, Pratesi G, Ragg EM, Gelmi ML, Contini A. Bioorg Med Chem. 2011 Sep 15;19(18):5291-9. doi: 10.1016/j.bmc.2011.08.016. Epub 2011 Aug 16.
Bis-2,3-heteroarylmaleimides and polyheterocondensed imides joined through nitrogen atoms of the N,N'-bis(ethyl)-1,3-propanediamine linker were prepared from substituted maleic anhydrides and symmetrical diamines in good to satisfactory yields and short reaction times using microwave heating. The novel molecules were shown to inhibit proliferation of human tumor cells (NCI-H460 lung carcinoma) and rat aortic smooth muscle cells (SMCs) with variable potencies. Compound 11a, the most potent one of the series, showed IC(50) values comparable to those observed for the leading molecule elinafide in both cell lines, but with a higher selectivity toward human tumor cells. Compound 11a affected G1/S phase transition of the cell cycle, showed in vitro DNA intercalating activity and in vivo antitumor activity. A thorough structural analysis of the 11a-DNA complex was also made by mean of NMR and computational techniques.
2.Naphthalimides as anti-cancer agents: synthesis and biological activity.
Braña MF1, Ramos A. Curr Med Chem Anticancer Agents. 2001 Nov;1(3):237-55.
Naphthalimides are a class of compounds with high antitumor activity upon a variety of murine and human tumor cells. These compounds bind to DNA by intercalation of the chromophore and two of them, mitonafide and amonafide, were used in clinical trials. The therapeutic properties of these lead drugs were improved by designing bisintercalating agents. One of these, elinafide, showed intense in vitro and in vivo activity and is currently being used in clinical trials against solid tumors. In this paper, the history of elinafide is described.
3.DNA sequence recognition by bispyrazinonaphthalimides antitumor agents.
Carrasco C1, Joubert A, Tardy C, Maestre N, Cacho M, Braña MF, Bailly C. Biochemistry. 2003 Oct 14;42(40):11751-61.
Bifunctional DNA intercalating agents have long attracted considerable attention as anticancer agents. One of the lead compounds in this category is the dimeric antitumor drug elinafide, composed of two tricyclic naphthalimide chromophores separated by an aminoalkyl linker chain optimally designed to permit bisintercalation of the drug into DNA. In an effort to optimize the DNA recognition capacity, different series of elinafide analogues have been prepared by extending the surface of the planar drug chromophore which is important for DNA sequence recognition. We report here a detailed investigation of the DNA sequence preference of three tetracyclic monomeric or dimeric pyrazinonaphthalimide derivatives. Melting temperature measurements and surface plasmon resonance (SPR) studies indicate that the dimerization of the tetracyclic planar chromophore considerably augments the affinity of the drug for DNA, polynucleotides, or hairpin oligonucleotides and promotes selective interaction with G.
4.Chromophore-modified bisnaphthalimides: DNA recognition, topoisomerase inhibition, and cytotoxic properties of two mono- and bisfuronaphthalimides.
Bailly C1, Carrasco C, Joubert A, Bal C, Wattez N, Hildebrand MP, Lansiaux A, Colson P, Houssier C, Cacho M, Ramos A, Braña MF. Biochemistry. 2003 Apr 15;42(14):4136-50.
Bisnaphthalimides represent a promising group of DNA-targeted anticancer agents. In this series, the lead compounds elinafide and bisnafide have reached clinical trials, and the search for more potent analogues remains a priority. In the course of a medicinal chemistry program aimed at discovering novel antitumor drugs based on the naphthalimide skeleton, different dimeric molecules containing two tetracyclic neutral DNA intercalating chromophores were synthesized. The naphthalimide unit has been fused to a benzene ring (azonafide derivatives), an imidazole, a pyrazine, or, as reported here, a furan ring which increases the planar surface of the chromophore and enhances its stacking properties. We report a detailed investigation of the DNA binding capacity of the dimeric molecule MCI3335 composed of two furonaphthalimide units connected by a 12 A long amino alkyl linker [(CH(2))(2)-NH-(CH(2))(3)-NH-(CH(2))(2)] identical to that of elinafide.
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CAS 162706-37-8 Elinafide

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