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MedKoo Cat#: 208423 | Name: Cyclostreptin

Description:

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

Cyclostreptin is an antitumor tubulin-polymerizing agent deficient in enhancing tubulin assembly despite its high affinity for the taxoid site

Chemical Structure

Cyclostreptin
Cyclostreptin
CAS#unknown

Theoretical Analysis

MedKoo Cat#: 208423

Name: Cyclostreptin

CAS#: unknown

Chemical Formula: C24H32O5

Exact Mass: 400.2250

Molecular Weight: 400.52

Elemental Analysis: C, 71.97; H, 8.05; O, 19.97

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
FR182877
IUPAC/Chemical Name
(1R,2R,4R,7R,8R,9R,10S,11R,12R,13S,17R,18R)-8,10-Dihydroxy-1,5,9,18-tetramethyl-16,20-dioxahexacyclo[15.3.2.02,13.04,12.07,11.014,19]docosa-5,14(19)-dien-15-one
InChi Key
WMRQHSFWMFGIFW-ZUEWXYCQSA-N
InChi Code
InChI=1S/C24H32O5/c1-9-7-13-17(21(26)11(3)20(13)25)16-12(9)8-14-18(16)19-22-10(2)15(28-23(19)27)5-6-24(14,4)29-22/h7,10-18,20-21,25-26H,5-6,8H2,1-4H3/t10-,11-,12+,13-,14-,15-,16+,17+,18-,20+,21-,24-/m1/s1
SMILES Code
O=C1C([C@@]2([H])[C@]3([H])[C@@]4([H])[C@H](O)[C@H](C)[C@H](O)[C@]4([H])C=C(C)[C@]3([H])C[C@@]2([H])[C@](CC5)(C)O6)=C6[C@H](C)[C@]5([H])O1
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 400.52 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.

Recalculate based on batch purity %
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: Calvo E, Barasoain I, Matesanz R, Pera B, Camafeita E, Pineda O, Hamel E, Vanderwal CD, Andreu JM, López JA, Díaz JF. Cyclostreptin derivatives specifically target cellular tubulin and further map the paclitaxel site. Biochemistry. 2012 Jan 10;51(1):329-41. doi: 10.1021/bi201380p. Epub 2011 Dec 30. PMID: 22148836; PMCID: PMC3255483. 2: Balaguer FA, Mühlethaler T, Estévez-Gallego J, Calvo E, Giménez-Abián JF, Risinger AL, Sorensen EJ, Vanderwal CD, Altmann KH, Mooberry SL, Steinmetz MO, Oliva MÁ, Prota AE, Díaz JF. Crystal Structure of the Cyclostreptin-Tubulin Adduct: Implications for Tubulin Activation by Taxane-Site Ligands. Int J Mol Sci. 2019 Mar 20;20(6):1392. doi: 10.3390/ijms20061392. PMID: 30897704; PMCID: PMC6471726. 3: Edler MC, Buey RM, Gussio R, Marcus AI, Vanderwal CD, Sorensen EJ, Díaz JF, Giannakakou P, Hamel E. Cyclostreptin (FR182877), an antitumor tubulin- polymerizing agent deficient in enhancing tubulin assembly despite its high affinity for the taxoid site. Biochemistry. 2005 Aug 30;44(34):11525-38. doi: 10.1021/bi050660m. Erratum in: Biochemistry. 2006 May 9;45(18):5932. PMID: 16114889. 4: Buey RM, Calvo E, Barasoain I, Pineda O, Edler MC, Matesanz R, Cerezo G, Vanderwal CD, Day BW, Sorensen EJ, López JA, Andreu JM, Hamel E, Díaz JF. Cyclostreptin binds covalently to microtubule pores and lumenal taxoid binding sites. Nat Chem Biol. 2007 Feb;3(2):117-25. doi: 10.1038/nchembio853. Epub 2007 Jan 7. PMID: 17206139. 5: Cao YN, Zheng LL, Wang D, Liang XX, Gao F, Zhou XL. Recent advances in microtubule-stabilizing agents. Eur J Med Chem. 2018 Jan 1;143:806-828. doi: 10.1016/j.ejmech.2017.11.062. Epub 2017 Nov 24. PMID: 29223097. 6: Prussia AJ, Yang Y, Geballe MT, Snyder JP. Cyclostreptin and microtubules: is a low-affinity binding site required? Chembiochem. 2010 Jan 4;11(1):101-9. doi: 10.1002/cbic.200900538. PMID: 19946930. 7: Bai R, Vanderwal CD, Díaz JF, Hamel E. Interaction of a cyclostreptin analogue with the microtubule taxoid site: the covalent reaction rapidly follows binding. J Nat Prod. 2008 Mar;71(3):370-4. doi: 10.1021/np800056m. Epub 2008 Feb 26. PMID: 18298077. 8: Hamel E, Day BW, Miller JH, Jung MK, Northcote PT, Ghosh AK, Curran DP, Cushman M, Nicolaou KC, Paterson I, Sorensen EJ. Synergistic effects of peloruside A and laulimalide with taxoid site drugs, but not with each other, on tubulin assembly. Mol Pharmacol. 2006 Nov;70(5):1555-64. doi: 10.1124/mol.106.027847. Epub 2006 Aug 3. PMID: 16887932. 9: Snyder JP. The microtubule-pore gatekeeper. Nat Chem Biol. 2007 Feb;3(2):81-2. doi: 10.1038/nchembio0207-81. PMID: 17235340. 10: Field JJ, Pera B, Calvo E, Canales A, Zurwerra D, Trigili C, Rodríguez- Salarichs J, Matesanz R, Kanakkanthara A, Wakefield SJ, Singh AJ, Jiménez- Barbero J, Northcote P, Miller JH, López JA, Hamel E, Barasoain I, Altmann KH, Díaz JF. Zampanolide, a potent new microtubule-stabilizing agent, covalently reacts with the taxane luminal site in tubulin α,β-heterodimers and microtubules. Chem Biol. 2012 Jun 22;19(6):686-98. doi: 10.1016/j.chembiol.2012.05.008. PMID: 22726683; PMCID: PMC3383615.

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