Elinafide

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 201220

CAS#: 162706-37-8,

Description: LU 79553, also known as LU 79553, is a novel DNA intercalator with potent antitumor activity which is highly cytotoxic in vitro with EC50 (concentration required for 50% inhibition of growth) ranging from 2 x 10(-7) to 5 x 10(-10) M. LU-79553 is also a DNA-binding topoisomerase II inhibitor that is particularly effective against human solid tumors that are refractory to other drugs.


Chemical Structure

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Elinafide
CAS# 162706-37-8,

Theoretical Analysis

MedKoo Cat#: 201220
Name: Elinafide
CAS#: 162706-37-8,
Chemical Formula: C31H28N4O4
Exact Mass: 520.21106
Molecular Weight: 520.57842
Elemental Analysis: C, 71.52; H, 5.42; N, 10.76; O, 12.29

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Synonym: LU79553; LU 79553; LU-79553; Elinafide

IUPAC/Chemical Name: 2-[2-[3-[2-(1,3-dioxobenzo[e]isoindol-2-yl)ethylamino]propylamino]ethyl]benzo[e]isoindole-1,3-dione.

InChi Key: CSAUBGZZOLHVPD-UHFFFAOYSA-N

InChi Code: InChI=1S/C31H28N4O4/c36-28-24-12-10-20-6-1-3-8-22(20)26(24)30(38)34(28)18-16-32-14-5-15-33-17-19-35-29(37)25-13-11-21-7-2-4-9-23(21)27(25)31(35)39/h1-4,6-13,32-33H,5,14-19H2

SMILES Code: O=C(C1=C2C=CC3=CC=CC=C13)N(CCNCCCNCCN(C(C4=C5C=CC6=CC=CC=C46)=O)C5=O)C2=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not soluble in water.

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 520.57842 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: González-Bulnes L, Gallego J. Indirect effects modulating the interaction between DNA and a cytotoxic bisnaphthalimide reveal a two-step binding process. J Am Chem Soc. 2009 Jun 10;131(22):7781-91. PubMed PMID: 19449871.

2: Antonini I, Santoni G, Lucciarini R, Amantini C, Sparapani S, Magnano A. Synthesis and biological evaluation of new asymmetrical bisintercalators as potential antitumor drugs. J Med Chem. 2006 Nov 30;49(24):7198-207. PubMed PMID: 17125272.

3: Gallego J. Sequence-dependent nucleotide dynamics revealed by intercalated ring rotation in DNA-bisnaphthalimide complexes. Nucleic Acids Res. 2004 Jul 7;32(12):3607-14. Print 2004. PubMed PMID: 15240833; PubMed Central PMCID: PMC484180.

4: Braña MF, Cacho M, García MA, de Pascual-Teresa B, Ramos A, Domínguez MT, Pozuelo JM, Abradelo C, Rey-Stolle MF, Yuste M, Báñez-Coronel M, Lacal JC. New analogues of amonafide and elinafide, containing aromatic heterocycles: synthesis, antitumor activity, molecular modeling, and DNA binding properties. J Med Chem. 2004 Mar 11;47(6):1391-9. PubMed PMID: 14998328.

5: Carrasco C, Joubert A, Tardy C, Maestre N, Cacho M, Braña MF, Bailly C. DNA sequence recognition by bispyrazinonaphthalimides antitumor agents. Biochemistry. 2003 Oct 14;42(40):11751-61. PubMed PMID: 14529286.

6: Braña MF, Cacho M, Ramos A, Domínguez MT, Pozuelo JM, Abradelo C, Rey-Stolle MF, Yuste M, Carrasco C, Bailly C. Synthesis, biological evaluation and DNA binding properties of novel mono and bisnaphthalimides. Org Biomol Chem. 2003 Feb 21;1(4):648-54. PubMed PMID: 12929451.

7: Bailly C, Carrasco C, Joubert A, Bal C, Wattez N, Hildebrand MP, Lansiaux A, Colson P, Houssier C, Cacho M, Ramos A, Braña MF. Chromophore-modified bisnaphthalimides: DNA recognition, topoisomerase inhibition, and cytotoxic properties of two mono- and bisfuronaphthalimides. Biochemistry. 2003 Apr 15;42(14):4136-50. PubMed PMID: 12680768.

8: Braña MF, Ramos A. Naphthalimides as anti-cancer agents: synthesis and biological activity. Curr Med Chem Anticancer Agents. 2001 Nov;1(3):237-55. Review. PubMed PMID: 12678756.

9: Kong Thoo Lin P, Dance AM, Bestwick C, Milne L. The biological activities of new polyamine derivatives as potential therapeutic agents. Biochem Soc Trans. 2003 Apr;31(2):407-10. Review. PubMed PMID: 12653648.

10: Awada A, Thödtmann R, Piccart MJ, Wanders J, Schrijvers AH, Von Broen IM, Hanauske AR; EORTC-ECSG phase I study. An EORTC-ECSG phase I study of LU 79553 administered every 21 or 42 days in patients with solid tumours. Eur J Cancer. 2003 Apr;39(6):742-7. PubMed PMID: 12651198.

Elinafide

10.0mg / Not available


Additional Information

LU 79553 is a novel bis-naphthalimide which is highly cytotoxic in vitro with EC50 (concentration required for 50% inhibition of growth) ranging from 2 x 10(-7) to 5 x 10(-10) M. A number of studies were conducted to examine its antitumor activity in human xenograft models.  Complete regression of MX-1 (mammary carcinoma) xenografts was observed when LU 79553 was administered i.v. daily for 5 doses at 20 mg/kg (2 cycles starting on Days 6 and 20) or every 3 days for 2 doses at 55 mg/kg (2 cycles starting on Days 6 and 13) or every 7 days for 4 doses. Complete regression was also seen in the MX-1 model when tumors were staged at 1-2 g prior to the initiation of treatment. Regressions (complete or partial) were observed in the LX-1 (lung), CX-1 (colon), DLD (colon), and LOX (melanoma) xenograft models. A significant increase in the median survival time of OVCAR-3- (ovarian carcinoma) bearing mice was noted in LU 79553-treated animals (treated/control = 195%). The excellent activity of this compound in such a wide variety of tumor types suggests LU 79553 merits further investigation in clinical trials. see: http://www.ncbi.nlm.nih.gov/pubmed/7867004.