Hemiasterlin

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

MedKoo CAT#: 562709

CAS#: 157207-90-4

Description: Hemiasterlin is a cytotoxic peptide. It acts by inducing mitotic arrest and abnormal spindle formation.


Chemical Structure

img
Hemiasterlin
CAS# 157207-90-4

Theoretical Analysis

MedKoo Cat#: 562709
Name: Hemiasterlin
CAS#: 157207-90-4
Chemical Formula: C30H46N4O4
Exact Mass: 526.3519
Molecular Weight: 526.72
Elemental Analysis: C, 68.41; H, 8.80; N, 10.64; O, 12.15

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Hemiasterlin; NSC695242; Milnamide B; (-)-Hemiasterlin; NSC-695242; NSC 695242;

IUPAC/Chemical Name: (S,E)-2,5-dimethyl-4-((S)-N,3,3-trimethyl-2-((S)-3-methyl-3-(1-methyl-1H-indol-3-yl)-2-(methylamino)butanamido)butanamido)hex-2-enoic acid

InChi Key: KQODQNJLJQHFQV-MKWZWQCGSA-N

InChi Code: InChI=1S/C30H46N4O4/c1-18(2)23(16-19(3)28(37)38)34(11)27(36)25(29(4,5)6)32-26(35)24(31-9)30(7,8)21-17-33(10)22-15-13-12-14-20(21)22/h12-18,23-25,31H,1-11H3,(H,32,35)(H,37,38)/b19-16+/t23-,24-,25-/m1/s1

SMILES Code: OC(/C(C)=C/[C@H](C(C)C)N(C)C([C@@H](NC([C@@H](NC)C(C)(C)C1=CN(C)C2=CC=CC=C12)=O)C(C)(C)C)=O)=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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 526.72 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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Lang JH, Jones PG, Lindel T. Total Synthesis of the Marine Natural Product Hemiasterlin by Organocatalyzed α-Hydrazination. Chemistry. 2017 Sep 18;23(52):12714-12717. doi: 10.1002/chem.201702812. Epub 2017 Aug 16. PubMed PMID: 28727177.

2: Seiler R, Oo HZ, Tortora D, Clausen TM, Wang CK, Kumar G, Pereira MA, Ørum-Madsen MS, Agerbæk MØ, Gustavsson T, Nordmaj MA, Rich JR, Lallous N, Fazli L, Lee SS, Douglas J, Todenhöfer T, Esfandnia S, Battsogt D, Babcook JS, Al-Nakouzi N, Crabb SJ, Moskalev I, Kiss B, Davicioni E, Thalmann GN, Rennie PS, Black PC, Salanti A, Daugaard M. An Oncofetal Glycosaminoglycan Modification Provides Therapeutic Access to Cisplatin-resistant Bladder Cancer. Eur Urol. 2017 Jul;72(1):142-150. doi: 10.1016/j.eururo.2017.03.021. Epub 2017 Apr 10. PubMed PMID: 28408175.

3: Lai WT, Cheng KL, Baruchello R, Rondanin R, Marchetti P, Simoni D, Lee RM, Guh JH, Hsu LC. Hemiasterlin derivative (R)(S)(S)-BF65 and Akt inhibitor MK-2206 synergistically inhibit SKOV3 ovarian cancer cell growth. Biochem Pharmacol. 2016 Aug 1;113:12-23. doi: 10.1016/j.bcp.2016.06.010. Epub 2016 Jun 17. PubMed PMID: 27328368.

4: 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. PubMed PMID: 27262542.

5: Lesma G, Bassanini I, Bortolozzi R, Colletto C, Bai R, Hamel E, Meneghetti F, Rainoldi G, Stucchi M, Sacchetti A, Silvani A, Viola G. Complementary isonitrile-based multicomponent reactions for the synthesis of diversified cytotoxic hemiasterlin analogues. Org Biomol Chem. 2015 Dec 28;13(48):11633-44. doi: 10.1039/c5ob01882j. Epub 2015 Oct 15. PubMed PMID: 26467486; PubMed Central PMCID: PMC4685954.

6: Salanti A, Clausen TM, Agerbæk MØ, Al Nakouzi N, Dahlbäck M, Oo HZ, Lee S, Gustavsson T, Rich JR, Hedberg BJ, Mao Y, Barington L, Pereira MA, LoBello J, Endo M, Fazli L, Soden J, Wang CK, Sander AF, Dagil R, Thrane S, Holst PJ, Meng L, Favero F, Weiss GJ, Nielsen MA, Freeth J, Nielsen TO, Zaia J, Tran NL, Trent J, Babcook JS, Theander TG, Sorensen PH, Daugaard M. Targeting Human Cancer by a Glycosaminoglycan Binding Malaria Protein. Cancer Cell. 2015 Oct 12;28(4):500-514. doi: 10.1016/j.ccell.2015.09.003. PubMed PMID: 26461094; PubMed Central PMCID: PMC4790448.

7: Dang T, Pham TC, Ngo QA, Vu T, Nguyen TD, Doan DT, Ba TC, Jean M, van de Weghe P, Nguyen VT. Synthesis of new bioisosteric hemiasterlin analogues with extremely high cytotoxicity. Bioorg Med Chem Lett. 2014 Nov 15;24(22):5216-8. doi: 10.1016/j.bmcl.2014.09.065. Epub 2014 Oct 2. PubMed PMID: 25442315.

8: The CP, Thi TA, Hoang TP, Ngo QA, Doan DT, Thi TH, Thi TP, Thi TH, Jean M, van de Weghe P, Van TN. Synthesis of new simplified hemiasterlin derivatives with α,β-unsaturated carbonyl moiety. Bioorg Med Chem Lett. 2014 May 15;24(10):2244-6. doi: 10.1016/j.bmcl.2014.03.091. Epub 2014 Apr 5. PubMed PMID: 24745968.

9: Lesma G, Sacchetti A, Bai R, Basso G, Bortolozzi R, Hamel E, Silvani A, Vaiana N, Viola G. Hemiasterlin analogues incorporating an aromatic, and heterocyclic type C-terminus: design, synthesis and biological evaluation. Mol Divers. 2014 May;18(2):357-73. doi: 10.1007/s11030-014-9507-9. Epub 2014 Feb 6. PubMed PMID: 24500310; PubMed Central PMCID: PMC4081462.

10: Rocha-Lima CM, Bayraktar S, Macintyre J, Raez L, Flores AM, Ferrell A, Rubin EH, Poplin EA, Tan AR, Lucarelli A, Zojwalla N. A phase 1 trial of E7974 administered on day 1 of a 21-day cycle in patients with advanced solid tumors. Cancer. 2012 Sep 1;118(17):4262-70. doi: 10.1002/cncr.27428. Epub 2012 Jan 31. PubMed PMID: 22294459.

11: Hsu LC, Durrant DE, Huang CC, Chi NW, Baruchello R, Rondanin R, Rullo C, Marchetti P, Grisolia G, Simoni D, Lee RM. Development of hemiasterlin derivatives as potential anticancer agents that inhibit tubulin polymerization and synergize with a stilbene tubulin inhibitor. Invest New Drugs. 2012 Aug;30(4):1379-88. doi: 10.1007/s10637-011-9702-9. Epub 2011 Jun 8. PubMed PMID: 21655917.

12: Simoni D, Lee RM, Durrant DE, Chi NW, Baruchello R, Rondanin R, Rullo C, Marchetti P. Versatile synthesis of new cytotoxic agents structurally related to hemiasterlins. Bioorg Med Chem Lett. 2010 Jun 1;20(11):3431-5. doi: 10.1016/j.bmcl.2010.03.098. Epub 2010 Apr 1. PubMed PMID: 20430617.

13: Zubovych IO, Straud S, Roth MG. Mitochondrial dysfunction confers resistance to multiple drugs in Caenorhabditis elegans. Mol Biol Cell. 2010 Mar 15;21(6):956-69. doi: 10.1091/mbc.E09-08-0673. Epub 2010 Jan 20. PubMed PMID: 20089839; PubMed Central PMCID: PMC2836976.

14: Kuznetsov G, TenDyke K, Towle MJ, Cheng H, Liu J, Marsh JP, Schiller SE, Spyvee MR, Yang H, Seletsky BM, Shaffer CJ, Marceau V, Yao Y, Suh EM, Campagna S, Fang FG, Kowalczyk JJ, Littlefield BA. Tubulin-based antimitotic mechanism of E7974, a novel analogue of the marine sponge natural product hemiasterlin. Mol Cancer Ther. 2009 Oct;8(10):2852-60. doi: 10.1158/1535-7163.MCT-09-0301. PubMed PMID: 19825803.

15: Matsui Y, Hadaschik BA, Fazli L, Andersen RJ, Gleave ME, So AI. Intravesical combination treatment with antisense oligonucleotides targeting heat shock protein-27 and HTI-286 as a novel strategy for high-grade bladder cancer. Mol Cancer Ther. 2009 Aug;8(8):2402-11. doi: 10.1158/1535-7163.MCT-09-0148. Epub 2009 Jul 22. PubMed PMID: 19625496.

16: Kingston DG. Tubulin-interactive natural products as anticancer agents. J Nat Prod. 2009 Mar 27;72(3):507-15. doi: 10.1021/np800568j. Review. Erratum in: J Nat Prod. 2011 May 27;74(5):1352. PubMed PMID: 19125622; PubMed Central PMCID: PMC2765517.

17: Singh R, Sharma M, Joshi P, Rawat DS. Clinical status of anti-cancer agents derived from marine sources. Anticancer Agents Med Chem. 2008 Aug;8(6):603-17. Review. PubMed PMID: 18690825.

18: Balasubramanian R, Raghavan B, Steele JC, Sackett DL, Fecik RA. Tubulysin analogs incorporating desmethyl and dimethyl tubuphenylalanine derivatives. Bioorg Med Chem Lett. 2008 May 1;18(9):2996-9. doi: 10.1016/j.bmcl.2008.03.046. Epub 2008 Mar 20. PubMed PMID: 18411048.

19: Moody TW, Pradhan T, Mantey SA, Jensen RT, Dyba M, Moody D, Tarasova NI, Michejda CJ. Bombesin marine toxin conjugates inhibit the growth of lung cancer cells. Life Sci. 2008 Apr 9;82(15-16):855-61. doi: 10.1016/j.lfs.2008.01.019. Epub 2008 Feb 14. PubMed PMID: 18336841; PubMed Central PMCID: PMC2695325.

20: Hadaschik BA, Adomat H, Fazli L, Fradet Y, Andersen RJ, Gleave ME, So AI. Intravesical chemotherapy of high-grade bladder cancer with HTI-286, a synthetic analogue of the marine sponge product hemiasterlin. Clin Cancer Res. 2008 Mar 1;14(5):1510-8. doi: 10.1158/1078-0432.CCR-07-4475. PubMed PMID: 18316576.