Eilatin
Eilatin is a seven-ring pyridoacridine marine alkaloid with anticancer, antibacterial, and antiparasitic activities. Eilatin acts as a DNA intercalator with selectivity for electron-deficient polycyclic purines; it can chelate Ni2+ ions and cleave DNA via hydroxyl radical generation. Eilatin induces the SOS response in bacteria, inhibits cancer cell proliferation, and induces cancer cell differentiation and reversion of transformation. The IC50 of Eilatin against Trypanosoma brucei brucei is 1.33 μM. Eilatin can be used in research related to colon tumors, neuroblastoma, chronic myeloid leukemia, acute myeloid leukemia, and trypanosome infections.
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- CAS. Nr.: 120154-96-3
- Formel: C24H12N4
- Molecular Weight:356.38
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Speicherung:
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Biologische Aktivität
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Biologische Aktivität
Beschreibung
IC50 & Target
[7]|
Trypanosoma brucei brucei 1.33 μM (IC50) |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
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| HCT-116 | IC50 |
5.3 μM
Compound: 7 (Eilatin)
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Tested for the cytotoxicity to inhibit replication assay against the human colon tumor cell line HCT116
Tested for the cytotoxicity to inhibit replication assay against the human colon tumor cell line HCT116
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[PMID: 7525959] |
In Vitro
Eilatin (18 h) inhibits the proliferation of human colon cancer cell line HCT116, with an IC50 value of 5.3 μM[1].
Eilatin (10-7-10-6 M; 16 h) inhibits the proliferation of bone marrow CFU-C from patients with chronic-phase Ph+ chronic myeloid leukemia, as well as CD34+ cells from patients with chronic-phase and blast-phase Ph+ chronic myeloid leukemia, in vitro. At a concentration of 10-7 M, it reduces the BCR/ABL fusion signal in Ph+ chronic myeloid leukemia CD34+ cells to 54.5%. Meanwhile, it exerts dose-dependent antileukemic effects on the aforementioned Ph+ cells[3].
Pretreatment with Eilatin (10-7 M; 16 h) significantly reduces the proportion of bcr/abl-positive cells in bone marrow cells from patients with chronic myeloid leukemia (CML) following 7 days of culture with an interleukin-11-containing cytokine cocktail or medium alone[5].
Eilatin (3 h) induces SOS response in the λ-lacZ lysogenic Escherichia coli strain BR513-84 at doses higher than 2 μg/disk[1].
Eilatin (2.8 μM) can intercalate into calf thymus DNA, which is manifested as a concentration-dependent increase in fluorescence intensity with the increase of DNA dosage (50-450 μg) at an excitation wavelength of 520 nm.[1]
Eilatin (0.12-0.16 μM) potently inhibits the proliferation of mouse neuroblastoma N1E-115 cells and induces stable and irreversible morphological differentiation in these cells, with the effect being sustained long-term after a single administration[2].
Eilatin (0.2-2 μM; 0-6 days) dose-dependently slows the proliferation of normal hamster fibroblast NIL8, and induces significant cell flattening and volume enlargement in these cells, with no cytotoxicity observed at concentrations up to 0.5 μM[2].
Eilatin (0.05-0.5 μM; 0-6 days) potently inhibits the proliferation of hamster sarcoma virus-transformed NIL8-HSV fibroblasts and induces stable and irreversible reversion of their transformed phenotype; complete growth arrest is achieved at concentrations of 0.1-0.2 μM, while cytotoxicity is observed at 0.5 μM[2].
Eilatin (10-8-10-6 M; 16 h) inhibits the growth of CFU-GM in non-adherent human bone marrow myeloid progenitor cells and human umbilical cord blood myeloid progenitor cells in a dose-dependent manner; compared with umbilical cord blood cells (with a maximum inhibition rate of 50% at 10-6 M), bone marrow cells exhibit significantly stronger inhibition (with an inhibition rate of up to 100% at 10-6 M)[4].
Eilatin (10-6 M; 16 h exposure followed by 7-day liquid culture) exerts a similar degree of inhibitory effect on secondary colony formation of non-adherent human bone marrow myeloid progenitor cells and human umbilical cord blood myeloid progenitor cells, yet the secondary plating efficiency (self-renewal capacity) of cord blood cells remains significantly higher than that of bone marrow cells[4].
Eilatin (10-6 M; 16 h exposure, followed by 7-day liquid culture) does not cause significant differences in cell recovery capacity between non-adherent human bone marrow myeloid progenitor cells and human umbilical cord blood myeloid progenitor cells after 7 days of liquid culture[4].
Eilatin (10-7 M; 16 h) exerts a stronger inhibitory effect on CFU-C proliferation in bone marrow cells from patients with chronic myeloid leukemia (CML) than in bone marrow cells from healthy individuals; moreover, after pretreatment with Eilatin, interleukin-11 combined with interleukin-3 and granulocyte-macrophage colony-stimulating factor significantly promotes CFU-C colony growth in both cell types[5].
Eilatin (10-7 M; 16 h pre-treatment) reduces the total cell recovery rate of normal cells and chronic myeloid leukemia (CML) bone marrow cells in suspension culture, whereas the combination of interleukin-11 with interleukin-3 and granulocyte-macrophage colony-stimulating factor significantly enhances the secondary CFU-C colony-forming ability of both Eilatin-pretreated cell types[5].
Eilatin potently inhibits the growth of *Trypanosoma brucei*, with an IC50 of 1.33 μM; at concentrations as high as 83 μM, its maximum inhibition rate against HEK293 cells reaches 62.1%[6][7].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:mouse neuroblastoma N1E-115 cells
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Concentration:0.14 μM
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Incubation Time:3 days; 6 days
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Result:Induced morphological differentiation characterized by cells flattening onto the surface, increasing considerably in size (some reaching a soma perimeter of 1,000 μm), and extending relatively few but very thick neurites.
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Cell Line:normal hamster fibroblast NIL8 cells and hamster sarcoma virus-transformed NIL8-HSV fibroblasts
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Concentration:0.2, 0.5 and 0.2 μM (NIL8 cells); 0.05; 0.1, 0.15, 0.2 and 0.05 μM (NIL8-HSV)
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Incubation Time:0, 1, 2, 3, 4, 5 and 6 days
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Result:NIL8 cells: inhibited cell growth in a dose-dependent manner: 0.05 μM had no effect, 0.1-0.2 μM slowed cell multiplication, and 0.5 μM did not cause cytotoxicity.
Caused cells to increase considerably in size (exceeding 800 μm in perimeter), become extremely flattened, and exhibit a very low saturation density due to increased size and adhesiveness to the substratum at 1.4 μM.
NIL8-HSV cells: Potently inhibited cell proliferation: 0.05 μM slowed multiplication and reduced saturation density, 0.1-0.2 μM practically halted cell multiplication, and 0.5 μM was cytotoxic.
Induced stable reverse transformation with a single application: cells became exceptionally large (average surface area of ~8,000 μm2, doubling to 16,000 μm2 7 days after drug removal), flattened, regained contact inhibition of growth, and assembled microfilament bundles (stress fibers) in ~65% of cells.
Rendered effects not reversible upon drug removal.
Chemical Information
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CAS. Nr. 120154-96-3
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Molecular Weight 356.38
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Formel C24H12N4
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SMILES
C1(C2=C(N=C3C4=C5C6=NC=CC5=C7C=CC=CC7=N4)C=CC=C2)=C3C6=NC=C1
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Versand
Room temperature in continental US; may vary elsewhere.
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Speicherung
Please store the product under the recommended conditions in the Certificate of Analysis.
Reinheit & Dokumentation
Verweise
[1]. McDonald LA, et al. Inhibition of topoisomerase II catalytic activity by pyridoacridine alkaloids from a Cystodytes sp. ascidian: a mechanism for the apparent intercalator-induced inhibition of topoisomerase II. Journal of medicinal chemistry. 1994 Oct 28;37(22):3819-27. [Content Brief]
[2]. Shochet NR, et al. Novel marine alkaloids from the tunicate Eudistoma sp. are potent regulators of cellular growth and differentiation and affect cAMP-mediated processes. Journal of cellular physiology. 1993 Dec;157(3):481-92. [Content Brief]
[3]. Einat M, et al. Eilatin: a novel marine alkaloid inhibits in vitro proliferation of progenitor cells in chronic myeloid leukemia patients. Experimental hematology. 1995 Dec;23(14):1439-44. [Content Brief]
[4]. Toren A, et al. Human umbilical cord blood myeloid progenitor cells are relatively chemoresistant: a potential model for autologous transplantations in HIV-infected newborns. American journal of hematology. 1997 Nov;56(3):161-7. [Content Brief]
[5]. Einat M, et al. Synergistic effects of interleukin-11 with other growth factors on the expansion of hematopoietic progenitors from normal individuals and chronic myeloid leukemia patients resistant to treatment with cytosine arabinoside or eilatin. Leukemia research. 1996 Sep;20(9):751-9. [Content Brief]
[6]. Camp D, et al. Drug-like properties: guiding principles for the design of natural product libraries. J Nat Prod. 2012 Jan 27;75(1):72-81. doi: 10.1021/np200687v. Epub 2011 Dec 28. PMID: 22204643. [Content Brief]
Calculators
Konzentration (Stammlösung) × Volumen (Stammlösung) = Konzentration (Ziellösung) × Volumen (Ziellösung)
Eilatin Related Classifications
HY-183242 Related Classifications
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