An inhibitor of Gal-1
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OTX008

Item No. 23130

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,2',2'',2'''-[pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-25,26,27,28-tetrayltetrakis(oxy)]tetrakis[N-[2-(dimethylamino)ethyl]-acetamide
CAS Number
286936-40-1
Synonyms
  • Calixarene 0118
  • PTX008
Molecular Formula
C52H72N8O8
Formula Weight
937.2
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 2 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 0.5 mg/ml
λmax
205 nm
SMILES
O=C(NCCN(C)C)COC1=C(C2)C=CC=C1CC3=CC=CC(CC4=CC=CC(CC5=CC=CC2=C5OCC(NCCN(C)C)=O)=C4OCC(NCCN(C)C)=O)=C3OCC(NCCN(C)C)=O
InChi Code
InChI=1S/C52H72N8O8/c1-57(2)25-21-53-45(61)33-65-49-37-13-9-14-38(49)30-40-16-11-18-42(51(40)67-35-47(63)55-23-27-59(5)6)32-44-20-12-19-43(52(44)68-36-48(64)56-24-28-60(7)8)31-41-17-10-15-39(29-37)50(41)66-34-46(62)54-22-26-58(3)4/h9-20H,21-36H2,1-8H3,(H,53,61)(H,54,62)(H,55,63)(H,56,64)
InChi Key
CQVAQQNDZCZBSU-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $75

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    1 mg

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    5 mg

    $589

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    10 mg

    $1,030

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    Cayman Chemical
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    Product Description

    OTX008 is a small molecule topomimetic of the antiangiogenic peptide anginex and an inhibitor of galectin-1 (Gal-1).1 It decreases lactose binding to Gal-1 with Kd values of 290 and 100 μM in the presence and absence of OTX008, respectively, and is cytotoxic against a cancer cell panel with IC50 values that directly correlate to Gal-1 mRNA expression. OTX008 inhibits proliferation of human umbilical vein endothelial cells (HUVECs; IC50 = 2 μM) and reduces HUVEC migration in a wound healing assay.2 OTX008 is angiostatic in a chorioallantoic membrane (CAM) assay, inducing formation of shorter, finer, and less defined vessels than vehicle control in fertilized chicken eggs. In vivo, OTX008 (2.4 and 10 mg/kg) reduces tumor growth in the MA148 ovarian mouse xenograft model and the B16 murine melanoma syngeneic model via decreases in tumor microvessel density and induction of apoptosis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dings, R.P.M., Miller, M.C., Nesmelova, I., et al. Antitumor agent calixarene 0118 targets human galectin-1 as an allosteric inhibitor of carbohydrate binding. J. Med. Chem. 55(11), 5121-5129 (2012).

    2. Dings, R.P.M., Chen, X., Hellebrekers, D.M.E.I., et al. Design of nonpeptidic topomimetics of antiangiogenic proteins with antitumor activities. J. Natl. Cancer Inst. 98(13), 932-936 (2006).