MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 202760 | Name: Taltobulin
Featured

Description:

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

Taltobulin, also known as HTI-286 and SPA-110, is a fully synthetic analog of the natural tripeptide hemiasterlin, inhibits tubulin polymerization and circumvents transport-based resistance to taxanes. HTI-286 was a potent inhibitor of proliferation (mean IC50 = 2.5 ± 2.1 nm in 18 human tumor cell lines) and had substantially less interaction with multidrug resistance protein (P-glycoprotein) than currently used antimicrotubule agents, including paclitaxel, docetaxel, vinorelbine, or vinblastine.

Chemical Structure

Taltobulin
Taltobulin
CAS#228266-40-8

Theoretical Analysis

MedKoo Cat#: 202760

Name: Taltobulin

CAS#: 228266-40-8

Chemical Formula: C27H43N3O4

Exact Mass: 473.3254

Molecular Weight: 473.65

Elemental Analysis: C, 68.47; H, 9.15; N, 8.87; O, 13.51

Price and Availability

Size Price Availability Quantity
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
HTI-286, HTI 286, HTI286, SPA-110, SPA110, SPA 110, Taltobulin
IUPAC/Chemical Name
(S,E)-4-(((S)-3,3-dimethyl-1-((S)-3-methyl-2-(methylamino)-3-phenylbutanamido)-1-oxobutan-2-yl)(methyl)amino)-2,5-dimethylhex-2-enoic acid
InChi Key
ORIMBSMIPMEOFU-PSRNMDMQSA-N
InChi Code
InChI=1S/C27H43N3O4/c1-17(2)20(16-18(3)25(33)34)30(10)22(26(4,5)6)24(32)29-23(31)21(28-9)27(7,8)19-14-12-11-13-15-19/h11-17,20-22,28H,1-10H3,(H,33,34)(H,29,31,32)/b18-16+/t20-,21-,22-/m1/s1
SMILES Code
CC(C)(C)[C@@H](C(NC([C@H](C(C)(C)C1=CC=CC=C1)NC)=O)=O)N([C@@H](C(C)C)/C=C(C(O)=O)\C)C
Appearance
Light yellow to yellow 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
>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
Taltobulin (HTI-286, SPA-110) is a novel antimitotic agent that inhibits the polymerization of tubulin, disrupts microtubule dynamics in cells and induces mitotic arrest and apoptosis. Relative to the antimicrotubule drugs in use, taltobulin exhibits significantly less interaction with the multidrug resistance protein (P-glycoprotein) and is effective in inhibiting human tumor xenografts in nude mouse models where paclitaxel and vincristine are ineffective. Taltobulin administered i.v. or p.o. in saline inhibits the growth of numerous human tumors without the side effects associated with formulations. Taltobulin is in clinical development. (from drugs of the future).

Preparing Stock Solutions

The following data is based on the product molecular weight 473.65 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: Szymczyk J, Czyrek A, Otlewski J, Zakrzewska M. FGF1 Protects MCF-7 Cells against Taltobulin through Both the MEKs/ERKs and PI3K/AKT Signaling Pathway. Biomedicines. 2023 Jun 29;11(7):1856. doi: 10.3390/biomedicines11071856. PMID: 37509496; PMCID: PMC10376943. 2: Szymczyk J, Sochacka M, Chudy P, Opalinski L, Otlewski J, Zakrzewska M. FGF1 protects FGFR1-overexpressing cancer cells against drugs targeting tubulin polymerization by activating AKT via two independent mechanisms. Front Oncol. 2022 Oct 6;12:1011762. doi: 10.3389/fonc.2022.1011762. PMID: 36276073; PMCID: PMC9582358. 3: Charoenpattarapreeda J, Walsh SJ, Carroll JS, Spring DR. Expeditious Total Synthesis of Hemiasterlin through a Convergent Multicomponent Strategy and Its Use in Targeted Cancer Therapeutics. Angew Chem Int Ed Engl. 2020 Dec 14;59(51):23045-23050. doi: 10.1002/anie.202010090. Epub 2020 Oct 12. PMID: 32894646; PMCID: PMC7756509. 4: Flores-Holguín N, Frau J, Glossman-Mitnik D. Conceptual DFT as a chemoinformatics tool for the study of the Taltobulin anticancer peptide. BMC Res Notes. 2019 Jul 19;12(1):442. doi: 10.1186/s13104-019-4478-7. PMID: 31324267; PMCID: PMC6642520. 5: Andersen RJ. Sponging off nature for new drug leads. Biochem Pharmacol. 2017 Sep 1;139:3-14. doi: 10.1016/j.bcp.2017.04.012. Epub 2017 Apr 12. PMID: 28411115. 6: Marchetti P, Pavan B, Simoni D, Baruchello R, Rondanin R, Mischiati C, Feriotto G, Ferraro L, Hsu LC, Lee RM, Dalpiaz A. A novel hybrid drug between two potent anti-tubulin agents as a potential prolonged anticancer approach. Eur J Pharm Sci. 2016 Aug 25;91:50-63. doi: 10.1016/j.ejps.2016.05.032. Epub 2016 Jun 1. PMID: 27262542. 7: Wang Y, Benz FW, Wu Y, Wang Q, Chen Y, Chen X, Li H, Zhang Y, Zhang R, Yang J. Structural Insights into the Pharmacophore of Vinca Domain Inhibitors of Microtubules. Mol Pharmacol. 2016 Feb;89(2):233-42. doi: 10.1124/mol.115.100149. Epub 2015 Dec 9. PMID: 26660762. 8: Niu C, Ho DM, Williamson RT, Zask A, Ayral-Kaloustian S. Absolute configurations of tubulin inhibitors taltobulin (HTI-286) and HTI-042 characterized by X-ray diffraction analysis and NMR studies. Bioorg Med Chem Lett. 2010 Mar 1;20(5):1535-8. doi: 10.1016/j.bmcl.2010.01.047. Epub 2010 Jan 20. Erratum in: Bioorg Med Chem Lett. 2012 Mar 1;22(5):2131. Williamson, Robert Thomas [added]. PMID: 20137930. 9: Vashist YK, Tiffon C, Stoupis C, Redaelli CA. Inhibition of hepatic tumor cell proliferation in vitro and tumor growth in vivo by taltobulin, a synthetic analogue of the tripeptide hemiasterlin. World J Gastroenterol. 2006 Nov 14;12(42):6771-8. doi: 10.3748/wjg.v12.i42.6771. PMID: 17106924; PMCID: PMC4087430. 10: Milton MJ, Thomas Williamson R, Koehn FE. Mapping the bound conformation and protein interactions of microtubule destabilizing peptides by STD-NMR spectroscopy. Bioorg Med Chem Lett. 2006 Aug 15;16(16):4279-82. doi: 10.1016/j.bmcl.2006.05.067. Epub 2006 Jun 12. PMID: 16765596. 11: Zask A, Kaplan J, Musto S, Loganzo F. Hybrids of the hemiasterlin analogue taltobulin and the dolastatins are potent antimicrotubule agents. J Am Chem Soc. 2005 Dec 21;127(50):17667-71. doi: 10.1021/ja053663v. PMID: 16351096. 12: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Oct;26(8):639-63. PMID: 15605126.