Elinafide - CAS 162706-37-8
Catalog number:
162706-37-8
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C31H28N4O4
Molecular Weight:
520.59
COA:
Inquire
Targets:
Topoisomerase
Description:
Elinafide, an isoquinoline derivative, has been found to be a Type II DNA topoisomerase inhibitor that was once developed in anticancer studies.
Publictions citing BOC Sciences Products
  • >> More
Purity:
98%
Appearance:
Powder
Synonyms:
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
Storage:
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).
MSDS:
Inquire
Quality Standard:
In-house standard
Quantity:
Milligram-Grams
InChIKey:
QUNOQBDEVTWCTA-UHFFFAOYSA-N
InChI:
InChI=1S/C31H28N4O4/c36-28-22-10-1-6-20-7-2-11-23(26(20)22)29(37)34(28)18-16-32-14-5-15-33-17-19-35-30(38)24-12-3-8-21-9-4-13-25(27(21)24)31(35)39/h1-4,6-13,32-33H,5,14-19H2
Canonical SMILES:
C1=CC2=C3C(=C1)C(=O)N(C(=O)C3=CC=C2)CCNCCCNCCN4C(=O)C5=CC=CC6=C5C(=CC=C6)C4=O
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.
Molecular Weight Calculator Molarity Calculator Solution Dilution Calculator

Related Topoisomerase Products


CAS 151271-53-3 UK-1

UK-1
(CAS: 151271-53-3)

UK-1, a benzoxazol derivative, has been found to a Streptomyces metabolite that could exhibit anticancer activity and topoisomerase II restraination activity.

CAS 519-23-3 Ellipticine

Ellipticine
(CAS: 519-23-3)

Ellipticine is a DNA intercalating agent and a DNA topoisomerase II inhibitor. Ellipticine is also a natural product, isolated in 1959 from the Australian everg...

CAS 33419-42-0 Etoposide

Etoposide
(CAS: 33419-42-0)

Etoposide is a semisynthetic derivative of podophyllotoxin, which inhibits DNA synthesis via topoisomerase II inhibition activity.

CAS 110311-30-3 Amrubicin hydrochloride

Amrubicin hydrochloride
(CAS: 110311-30-3)

Amrubicin hydrochloride is a topoisomerase II inhibitor used in the treatment of lung cancer.

CAS 161967-81-3 Grepafloxacin Hydrochloride

Grepafloxacin Hydrochloride
(CAS: 161967-81-3)

The hydrochloride salt form of Grepafloxacin, a fluoroquinolone derivative, has been found to be a Type II DNA topoisomerase inhibitor and was once studied as a...

CAS 211100-13-9 Sabarubicin

Sabarubicin
(CAS: 211100-13-9)

Sabarubicina, a disaccharide analogue of doxorubicin, is an antineoplastic agent which can intercalate into the DNA of tumor cells and interact with topoisomera...

CAS 78186-34-2 Bisantrene Dihydrochloride

Bisantrene Dihydrochloride
(CAS: 78186-34-2)

Bisantrene Dihydrochloride is the hydrochloride salt of Bisantrene. Bisantrene, also referred to CL-216942, Cyabin or NSC-337766, an anthracene bishydrazone der...

CAS 1562067-05-3 Banoxantrone D12

Banoxantrone D12
(CAS: 1562067-05-3)

The deuterium labeled banoxantrone which was rationally designed to have anti-tumor activity following bioreduction by tissue cytochrome P450 to AQ4, an active ...

Elomotecan HCl salt
(CAS: 220997-99-9)

Elomotecan, also referred to BN 80927 and R 1559, characterized by a stable seven-membered beta-hydroxylactone ring, is a DNA topoisomerase inhibitor. In vivo e...

CAS 123948-87-8 Topotecan

Topotecan
(CAS: 123948-87-8)

Topotecan has been used as a positive control for the identification and analysis of HIF-1α and VEGF inhibitors in human glioma cells under hypoxic conditions. ...

CAS 213819-48-8 Belotecan hydrochloride

Belotecan hydrochloride
(CAS: 213819-48-8)

Belotecan hydrochloride, also called as CKD-602 hydrochloride, a Topoisomerase I inhibitor, is the hydrochloride salt of the semi-synthetic and water-soluble ca...

ABT-719
(CAS: 162829-90-5)

ABT-719, a fluoroquinolone derivative, has been found to be a DNA topoisomerase inhibitor that was once developed in antibacterial studies.

CAS 174634-08-3 TAS-103

TAS-103
(CAS: 174634-08-3)

TAS-103, also known as BMS-247615, is a quinoline derivative that displays antitumor activity in murine and human tumor models. TAS-103 has been reported to be ...

Alatrofloxacin Mesylate
(CAS: 157605-25-9)

The mesylate salt form of alatrofloxacin, a fluoroquinolone derivative, has been found to be a Type II DNA topoisomerase inhibitor that was once developed to be...

CAS 57576-44-0 Aclarubicin

Aclarubicin
(CAS: 57576-44-0)

Aclarubicin is an oligosaccharide anthracycline antineoplastic antibiotic isolated from the bacterium Streptomyces galilaeus. It intercalates into DNA and inter...

CAS 70476-82-3 Mitoxantrone HCl

Mitoxantrone HCl
(CAS: 70476-82-3)

Mitoxantrone is a type II topoisomerase inhibitor with IC50 of 2.0 μM, 0.42 mM for HepG2 and MCF-7/wt cells, respectively.

CAS 97682-44-5 Irinotecan

Irinotecan
(CAS: 97682-44-5)

Irinotecan is a topoisomerase I inhibitor for LoVo cells and HT-29 cells with IC50 of 15.8 μM and 5.17 μM, respectively.

CAS 446-72-0 Genistein

Genistein
(CAS: 446-72-0)

Genistein, a phytoestrogen found in soy products, is a highly specific inhibitor of protein tyrosine kinase (PTK) which blocks the mitogenic effect mediated by ...

CAS 57852-57-0 Idarubicin Hydrochloride

Idarubicin Hydrochloride
(CAS: 57852-57-0)

Idarubicin HCl is a hydrochloride salt form of Idarubicin which is an anthracycline antibiotic and a DNA topoisomerase II (topo II) inhibitor for MCF-7 cells wi...

CAS 175519-16-1 Voreloxin Hydrochloride

Voreloxin Hydrochloride
(CAS: 175519-16-1)

Vosaroxin intercalates into DNA in a site-specific manner and blocks the re-ligation process carried out by topoisomerase II during DNA replication. As a result...

Chemical Structure

CAS 162706-37-8 Elinafide

Quick Inquiry

Verification code

Featured Items