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288847-35-8-OXI-4503 free base OXI-4503 free base

OXI-4503 free base

For research use only. Not for therapeutic Use.

  • CAT Number: I034058
  • CAS Number: 288847-35-8
  • Molecular Formula: C18H22O12P2
  • Molecular Weight: 492.31
  • Purity: 98%
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Related Small Molecules: WS 3     Efaproxiral     Nazartinib    

OXI-4503 Free Base is a diphosphate prodrug of cambretastatin A1.


Catalog Number I034058
CAS Number 288847-35-8
Synonyms

OXI-4503; OXI 4503; OXI4503

Molecular Formula C18H22O12P2
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name 1,2-Benzenediol, 3-methoxy-6-((1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl)-, 1,2-bis(dihydrogen phosphate)
InChI InChI=1S/C18H22O12P2/c1-25-13-8-7-12(16(29-31(19,20)21)18(13)30-32(22,23)24)6-5-11-9-14(26-2)17(28-4)15(10-11)27-3/h5-10H,1-4H3,(H2,19,20,21)(H2,22,23,24)/b6-5-
InChIKey GSOXMQLWUDQTNT-WAYWQWQTSA-N
SMILES COC1=C(OC)C(OC)=CC(/C=CC2=C(OP(O)(O)=O)C(OP(O)(O)=O)=C(OC)C=C2)=C1
Reference

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2: Chan LS, Daruwalla J, Christophi C. Selective targeting of the tumour vasculature. ANZ J Surg. 2008 Nov;78(11):955-67. doi: 10.1111/j.1445-2197.2008.04712.x. PMID: 18959693.
3: Thorpe PE. Vascular targeting agents as cancer therapeutics. Clin Cancer Res. 2004 Jan 15;10(2):415-27. doi: 10.1158/1078-0432.ccr-0642-03. PMID: 14760060.
4: Cai SX. Small molecule vascular disrupting agents: potential new drugs for cancer treatment. Recent Pat Anticancer Drug Discov. 2007 Jan;2(1):79-101. doi: 10.2174/157489207779561462. PMID: 18221055.
5: Shaked Y, Tang T, Woloszynek J, Daenen LG, Man S, Xu P, Cai SR, Arbeit JM, Voest EE, Chaplin DJ, Smythe J, Harris A, Nathan P, Judson I, Rustin G, Bertolini F, Link DC, Kerbel RS. Contribution of granulocyte colony-stimulating factor to the acute mobilization of endothelial precursor cells by vascular disrupting agents. Cancer Res. 2009 Oct 1;69(19):7524-8. doi: 10.1158/0008-5472.CAN-09-0381. Epub 2009 Sep 8. PMID: 19738066; PMCID: PMC2758166.
6: Johnson SP, Ogunlade O, Lythgoe MF, Beard P, Pedley RB. Longitudinal Photoacoustic Imaging of the Pharmacodynamic Effect of Vascular Targeted Therapy on Tumors. Clin Cancer Res. 2019 Dec 15;25(24):7436-7447. doi: 10.1158/1078-0432.CCR-19-0360. Epub 2019 Sep 24. PMID: 31551349.
7: Quatrale AE, Porcelli L, Gnoni A, Numico G, Paradiso A, Azzariti A. New vascular disrupting agents in upper gastrointestinal malignancies. Curr Med Chem. 2014;21(8):1039-49. doi: 10.2174/09298673113209990233. PMID: 23992324.
8: Cogle CR, Collins B, Turner D, Pettiford LC, Bossé R, Hawkins KE, Beachamp Z, Wise E, Cline C, May WS, Moreb JS, Hsu J, Hiemenz J, Brown R, Norkin M, Wingard JR, Uckun F. Safety, feasibility and preliminary efficacy of single agent combretastatin A1 diphosphate (OXi4503) in patients with relapsed or refractory acute myeloid leukemia or myelodysplastic syndromes. Br J Haematol. 2020 Jun;189(5):e211-e213. doi: 10.1111/bjh.16629. Epub 2020 Apr 1. PMID: 32236943.
9: Wittenborn TR, Horsman MR. Targeting tumour hypoxia to improve outcome of stereotactic radiotherapy. Acta Oncol. 2015;54(9):1385-92. doi: 10.3109/0284186X.2015.1064162. Epub 2015 Sep 2. PMID: 26329662.
10: d’Esposito A, Sweeney PW, Ali M, Saleh M, Ramasawmy R, Roberts TA, Agliardi G, Desjardins A, Lythgoe MF, Pedley RB, Shipley R, Walker-Samuel S. Computational fluid dynamics with imaging of cleared tissue and of in vivo perfusion predicts drug uptake and treatment responses in tumours. Nat Biomed Eng. 2018 Oct;2(10):773-787. doi: 10.1038/s41551-018-0306-y. Epub 2018 Oct 10. PMID: 31015649.

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