Fosbretabulin | CAS#222030-63-9 | antitumor

MedKoo Cat#: 584364 | Name: Fosbretabulin free acid

Description:

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

Fosbretabulin is a natural cis-stilbene which interferes with the cellular tubulin dynamics and which selectively destroys tumour blood vessels. Its pharmacological shortcomings such as insufficient chemical stability, water solubility, and cytotoxicity can be remedied by employing its imidazole derivatives.

Chemical Structure

Fosbretabulin free acid

CAS#222030-63-9 (free acid)

Theoretical Analysis

MedKoo Cat#: 584364

Name: Fosbretabulin free acid

CAS#: 222030-63-9 (free acid)

Chemical Formula: C18H21O8P

Exact Mass: 396.0974

Molecular Weight: 396.33

Elemental Analysis: C, 54.55; H, 5.34; O, 32.29; P, 7.82

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.

Bulk Inquiry

Related CAS #

168555-66-6 (disodium) 222030-63-9 (free acid) 404886-32-4 ( tromethamine)

Synonym

Fosbretabulin; CA4DP; Combretastatin A-4; Phosbretabulin; Combretastatin A4 phosphate; Fosbretabulina; Fosbretabuline;

IUPAC/Chemical Name

Phenol, 2-methoxy-5-((1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl)-, dihydrogen phosphate

InChi Key

WDOGQTQEKVLZIJ-WAYWQWQTSA-N

InChi Code

InChI=1S/C18H21O8P/c1-22-14-8-7-12(9-15(14)26-27(19,20)21)5-6-13-10-16(23-2)18(25-4)17(11-13)24-3/h5-11H,1-4H3,(H2,19,20,21)/b6-5-

SMILES Code

COC1=C(OC)C(OC)=CC(/C=C\C2=CC=C(OC)C(OP(O)(O)=O)=C2)=C1

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

Shelf Life

>2 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 396.33 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: Mahal K, Biersack B, Caysa H, Schobert R, Mueller T. Combretastatin A-4 derived imidazoles show cytotoxic, antivascular, and antimetastatic effects based on cytoskeletal reorganisation. Invest New Drugs. 2015 Jun;33(3):541-54. doi: 10.1007/s10637-015-0215-9. Epub 2015 Feb 14. PubMed PMID: 25678082. 2: Wen Z, Xu J, Wang Z, Qi H, Xu Q, Bai Z, Zhang Q, Bao K, Wu Y, Zhang W. 3-(3,4,5-Trimethoxyphenylselenyl)-1H-indoles and their selenoxides as combretastatin A-4 analogs: microwave-assisted synthesis and biological evaluation. Eur J Med Chem. 2015 Jan 27;90:184-94. doi: 10.1016/j.ejmech.2014.11.024. Epub 2014 Nov 13. PubMed PMID: 25461319. 3: Méndez-Callejas GM, Leone S, Tanzarella C, Antoccia A. Combretastatin A-4 induces p53 mitochondrial-relocalisation independent-apoptosis in non-small lung cancer cells. Cell Biol Int. 2014 Mar;38(3):296-308. doi: 10.1002/cbin.10199. Epub 2013 Nov 14. PubMed PMID: 24155061. 4: Madadi NR, Penthala NR, Howk K, Ketkar A, Eoff RL, Borrelli MJ, Crooks PA. Synthesis and biological evaluation of novel 4,5-disubstituted 2H-1,2,3-triazoles as cis-constrained analogues of combretastatin A-4. Eur J Med Chem. 2015 Oct 20;103:123-32. doi: 10.1016/j.ejmech.2015.08.041. Epub 2015 Aug 29. PubMed PMID: 26352674; PubMed Central PMCID: PMC4631050. 5: Guan Q, Yang F, Guo D, Xu J, Jiang M, Liu C, Bao K, Wu Y, Zhang W. Synthesis and biological evaluation of novel 3,4-diaryl-1,2,5-selenadiazol analogues of combretastatin A-4. Eur J Med Chem. 2014 Nov 24;87:1-9. doi: 10.1016/j.ejmech.2014.09.046. Epub 2014 Sep 16. PubMed PMID: 25233100. 6: Carvalho PC, Santos EA, Schneider BU, Matuo R, Pesarini JR, Cunha-Laura AL, Monreal AC, Lima DP, Antoniolli AC, Oliveira RJ. Diaryl sulfide analogs of combretastatin A-4: Toxicogenetic, immunomodulatory and apoptotic evaluations and prospects for use as a new chemotherapeutic drug. Environ Toxicol Pharmacol. 2015 Nov;40(3):715-21. doi: 10.1016/j.etap.2015.08.028. Epub 2015 Sep 2. PubMed PMID: 26410090. 7: Ma ZL, Yan XJ, Zhao L, Zhou JJ, Pang W, Kai ZP, Wu FH. Combretastatin A-4 and Derivatives: Potential Fungicides Targeting Fungal Tubulin. J Agric Food Chem. 2016 Feb 3;64(4):746-51. doi: 10.1021/acs.jafc.5b05119. Epub 2016 Jan 25. PubMed PMID: 26711170. 8: Xu Q, Qi H, Sun M, Zuo D, Jiang X, Wen Z, Wang Z, Wu Y, Zhang W. Synthesis and Biological Evaluation of 3-Alkyl-1,5-Diaryl-1H-Pyrazoles as Rigid Analogues of Combretastatin A-4 with Potent Antiproliferative Activity. PLoS One. 2015 Jun 10;10(6):e0128710. doi: 10.1371/journal.pone.0128710. eCollection 2015. PubMed PMID: 26061410; PubMed Central PMCID: PMC4462585. 9: Torijano-Gutiérrez S, Vilanova C, Díaz-Oltra S, Murga J, Falomir E, Carda M, Redondo-Horcajo M, Díaz JF, Barasoain I, Marco JA. The Mechanism of the Interactions of Pironetin Analog/Combretastatin A-4 Hybrids with Tubulin. Arch Pharm (Weinheim). 2015 Aug;348(8):541-7. doi: 10.1002/ardp.201500106. Epub 2015 Jun 17. PubMed PMID: 26085125. 10: Ke Q, Samad MA, Bae S, Chaplin DJ, Kang PM. Exaggerated hypertensive response to combretastatin A-4 phosphate in hypertensive rats: Effective pharmacological inhibition by diltiazem. Vascul Pharmacol. 2015 Nov;74:73-79. doi: 10.1016/j.vph.2015.05.004. Epub 2015 May 16. PubMed PMID: 25989107. 11: Sun J, Chen L, Liu C, Wang Z, Zuo D, Pan J, Qi H, Bao K, Wu Y, Zhang W. Synthesis and Biological Evaluations of 1,2-Diaryl Pyrroles as Analogues of Combretastatin A-4. Chem Biol Drug Des. 2015 Dec;86(6):1541-7. doi: 10.1111/cbdd.12617. Epub 2015 Sep 25. PubMed PMID: 26202587. 12: Gagné-Boulet M, Fortin S, Lacroix J, Lefebvre CA, Côté MF, C-Gaudreault R. Styryl-N-phenyl-N'-(2-chloroethyl)ureas and styrylphenylimidazolidin-2-ones as new potent microtubule-disrupting agents using combretastatin A-4 as model. Eur J Med Chem. 2015 Jul 15;100:34-43. doi: 10.1016/j.ejmech.2015.05.034. Epub 2015 May 28. PubMed PMID: 26069928. 13: Davydova MP, Sorokina IV, Tolstikova TG, Mamatyuk VI, Fadeev DS, Vasilevsky SF. [Synthesis of new analogues of combretastatin A-4 and the study of their anti-inflammatory activity]. Bioorg Khim. 2015 Jan-Feb;41(1):82-9. Russian. PubMed PMID: 26050475. 14: Vilanova C, Torijano-Gutiérrez S, Díaz-Oltra S, Murga J, Falomir E, Carda M, Alberto Marco J. Design and synthesis of pironetin analogue/combretastatin A-4 hybrids containing a 1,2,3-triazole ring and evaluation of their cytotoxic activity. Eur J Med Chem. 2014 Nov 24;87:125-30. doi: 10.1016/j.ejmech.2014.09.053. Epub 2014 Sep 16. PubMed PMID: 25240870. 15: Nkepang G, Bio M, Rajaputra P, Awuah SG, You Y. Folate receptor-mediated enhanced and specific delivery of far-red light-activatable prodrugs of combretastatin A-4 to FR-positive tumor. Bioconjug Chem. 2014 Dec 17;25(12):2175-88. doi: 10.1021/bc500376j. Epub 2014 Nov 21. PubMed PMID: 25351441; PubMed Central PMCID: PMC4275160. 16: Rajak H, Dewangan PK, Patel V, Jain DK, Singh A, Veerasamy R, Sharma PC, Dixit A. Design of combretastatin A-4 analogs as tubulin targeted vascular disrupting agent with special emphasis on their cis-restricted isomers. Curr Pharm Des. 2013;19(10):1923-55. Review. PubMed PMID: 23237054. 17: Zhang C, Zhou SS, Li XR, Wang BM, Lin NM, Feng LY, Zhang DY, Zhang LH, Wang JB, Pan JP. Enhanced antitumor activity by the combination of dasatinib and combretastatin A-4 in vitro and in vivo. Oncol Rep. 2013 Jun;29(6):2275-82. doi: 10.3892/or.2013.2405. Epub 2013 Apr 12. PubMed PMID: 23588374. 18: Yu K, Li R, Yang Z, Wang F, Wu W, Wang X, Nie C, Chen L. Discovery of a potent microtubule-targeting agent: Synthesis and biological evaluation of water-soluble amino acid prodrug of combretastatin A-4 derivatives. Bioorg Med Chem Lett. 2015 Jun 1;25(11):2302-7. doi: 10.1016/j.bmcl.2015.04.028. Epub 2015 Apr 16. PubMed PMID: 25933592. 19: Jiang J, Zheng C, Zhu K, Liu J, Sun N, Wang C, Jiang H, Zhu J, Luo C, Zhou Y. Quantum chemistry calculation-aided structural optimization of combretastatin A-4-like tubulin polymerization inhibitors: improved stability and biological activity. J Med Chem. 2015 Mar 12;58(5):2538-46. doi: 10.1021/acs.jmedchem.5b00118. Epub 2015 Feb 26. PubMed PMID: 25689111. 20: Do CV, Faouzi A, Barette C, Farce A, Fauvarque MO, Colomb E, Catry L, Berthier-Vergnes O, Haftek M, Barret R, Lomberget T. Synthesis and biological evaluation of thiophene and benzo[b]thiophene analogs of combretastatin A-4 and isocombretastatin A-4: A comparison between the linkage positions of the 3,4,5-trimethoxystyrene unit. Bioorg Med Chem Lett. 2016 Jan 1;26(1):174-80. doi: 10.1016/j.bmcl.2015.11.010. Epub 2015 Nov 10. PubMed PMID: 26602281.