OTX008 | PTX-008 | CAS#286936-40-1 | galectin-1 inhibitor

MedKoo Cat#: 205985 | Name: OTX008

Description:

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

OTX008 is a calixarene-based compound and galectin-1 (Gal-1) inhibitor with potential anti-angiogenic and antineoplastic activities. Upon subcutaneous administration, galectin-1 inhibitor OTX008 binds Gal-1 which leads to Gal-1 oxidation and proteosomal degradation through a not yet fully elucidated mechanism, and eventually downregulates Gal-1. This decreases tumor cell growth and inhibits angiogenesis. Gal-1, a multifunctional carbohydrate-binding protein, is often overexpressed on tumor cells and plays a key role in cancer cell proliferation, apoptosis, tumor angiogenesis and evasion of immune responses.

Chemical Structure

OTX008

CAS#286936-40-1

Theoretical Analysis

MedKoo Cat#: 205985

Name: OTX008

CAS#: 286936-40-1

Chemical Formula: C52H72N8O8

Exact Mass: 936.5473

Molecular Weight: 937.18

Elemental Analysis: C, 66.64; H, 7.74; N, 11.96; O, 13.66

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

OTX-008; OTX 008; OTX008; PTX008; PTX-008; PTX 008; calixarene 0118; N(2dimethylamino)ethyl)acetamidyl calix4arene.

IUPAC/Chemical Name

Acetamide, 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-5,11,17,23-tetrayltetrakis(oxy)]tetrakis[N-[2-(dimethylamino)ethyl]-.

InChi Key

VKOZKTMXYPDPOI-UHFFFAOYSA-N

InChi Code

InChI=1S/C52H72N8O8/c1-57(2)13-9-53-49(61)33-65-45-25-37-17-38(26-45)22-40-19-42(30-47(28-40)67-35-51(63)55-11-15-59(5)6)24-44-20-43(31-48(32-44)68-36-52(64)56-12-16-60(7)8)23-41-18-39(21-37)27-46(29-41)66-34-50(62)54-10-14-58(3)4/h17-20,25-32H,9-16,21-24,33-36H2,1-8H3,(H,53,61)(H,54,62)(H,55,63)(H,56,64)

SMILES Code

O=C(NCCN(C)C)COC1=C(CC2=C(OCC(NCCN(C)C)=O)C(CC3=CC=CC4=C3OCC(NCCN(C)C)=O)=CC=C2)C=CC=C1CC5=CC=CC(C4)=C5OCC(NCCN(C)C)=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 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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 937.18 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.

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

1: LÃ¤ppchen T, Dings RP, Rossin R, Simon JF, Visser TJ, Bakker M, Walhe P, van Mourik T, Donato K, van Beijnum JR, Griffioen AW, Lub J, Robillard MS, Mayo KH, GrÃ¼ll H. Novel analogs of antitumor agent calixarene 0118: Synthesis, cytotoxicity, click labeling with 2-[(18)F]fluoroethylazide, and in vivo evaluation. Eur J Med Chem. 2014 Oct 18;89C:279-295. doi: 10.1016/j.ejmech.2014.10.048. [Epub ahead of print] PubMed PMID: 25462244. 2: Astorgues-Xerri L, Riveiro ME, Tijeras-Raballand A, Serova M, Rabinovich GA, Bieche I, Vidaud M, de Gramont A, Martinet M, Cvitkovic E, Faivre S, Raymond E. OTX008, a selective small-molecule inhibitor of galectin-1, downregulates cancer cell proliferation, invasion and tumour angiogenesis. Eur J Cancer. 2014 Sep;50(14):2463-77. doi: 10.1016/j.ejca.2014.06.015. Epub 2014 Jul 16. PubMed PMID: 25042151. 3: Zucchetti M, Bonezzi K, Frapolli R, Sala F, Borsotti P, Zangarini M, Cvitkovic E, Noel K, Ubezio P, Giavazzi R, D'Incalci M, Taraboletti G. Pharmacokinetics and antineoplastic activity of galectin-1-targeting OTX008 in combination with sunitinib. Cancer Chemother Pharmacol. 2013 Oct;72(4):879-87. doi: 10.1007/s00280-013-2270-2. Epub 2013 Aug 24. PubMed PMID: 23978989. 4: Astorgues-Xerri L, Riveiro ME, Tijeras-Raballand A, Serova M, Neuzillet C, Albert S, Raymond E, Faivre S. Unraveling galectin-1 as a novel therapeutic target for cancer. Cancer Treat Rev. 2014 Mar;40(2):307-19. doi: 10.1016/j.ctrv.2013.07.007. Epub 2013 Aug 1. Review. PubMed PMID: 23953240. 5: Dings RP, Miller MC, Nesmelova I, Astorgues-Xerri L, Kumar N, Serova M, Chen X, Raymond E, Hoye TR, Mayo KH. Antitumor agent calixarene 0118 targets human galectin-1 as an allosteric inhibitor of carbohydrate binding. J Med Chem. 2012 Jun 14;55(11):5121-9. doi: 10.1021/jm300014q. Epub 2012 May 30. PubMed PMID: 22575017; PubMed Central PMCID: PMC4242090. 6: Dings RP, Van Laar ES, Webber J, Zhang Y, Griffin RJ, Waters SJ, MacDonald JR, Mayo KH. Ovarian tumor growth regression using a combination of vascular targeting agents anginex or topomimetic 0118 and the chemotherapeutic irofulven. Cancer Lett. 2008 Jul 8;265(2):270-80. doi: 10.1016/j.canlet.2008.02.048. Epub 2008 Apr 1. PubMed PMID: 18378392; PubMed Central PMCID: PMC3042303. 7: Dings RP, Chen X, Hellebrekers DM, van Eijk LI, Zhang Y, Hoye TR, Griffioen AW, Mayo KH. Design of nonpeptidic topomimetics of antiangiogenic proteins with antitumor activities. J Natl Cancer Inst. 2006 Jul 5;98(13):932-6. PubMed PMID: 16818857.