Agelastatin A

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MedKoo CAT#: 525251

CAS#: 152406-28-5

Description: Agelastatin A, also known as (-)-Agelastatin A, is β-Catenin Inhibitor. It is a member of the pyrrole-aminoimidazole marine alkaloid (PAI) family, possesses a unique tetracyclic structure and is one of the most potent anticancer PAIs isolated to date. Agelastatin A is 1.5 to 16 times more potent than cisplatin at inhibiting cell growth, its effects being most pronounced against human bladder, skin, colon, and breast carcinomas. Agelastatin A inhibits cancer cell proliferation by causing cells to accumulate in the G(2) phase of cell cycle.

Chemical Structure

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Agelastatin A
CAS# 152406-28-5
Instruction

Theoretical Analysis

MedKoo Cat#: 525251
Name: Agelastatin A
CAS#: 152406-28-5
Chemical Formula: C12H13BrN4O3
Exact Mass: 340.02
Molecular Weight: 341.165
Elemental Analysis: C, 42.25; H, 3.84; Br, 23.42; N, 16.42; O, 14.07

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.

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Synonym: (-)-Agelastatin A; Agelastatin A; Agelastatine A

IUPAC/Chemical Name: (5aS,5bS,8aS,9aR)-1-Bromo-8a-hydroxy-8-methyl-5,5a,5b,6,8,8a,9,9a-octahydroimidazo[4",5":4,5]cyclopenta[1,2-e]pyrrolo[1,2-a]pyrazine-4,7-dione

InChi Key: MPASKXAEPUAMBS-WJOUQXRDSA-N

InChi Code: InChI=1S/C12H13BrN4O3/c1-16-11(19)15-9-8-6(4-12(9,16)20)17-5(10(18)14-8)2-3-7(17)13/h2-3,6,8-9,20H,4H2,1H3,(H,14,18)(H,15,19)/t6-,8-,9+,12+/m1/s1

SMILES Code: O=C1C2=CC=C(Br)N2[C@@](C[C@]3(O)[C@@]4([H])NC(N3C)=O)([H])[C@@]4([H])N1

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 341.17 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Caulfield TR, Hayes KE, Qiu Y, Coban M, Seok Oh J, Lane AL, Yoshimitsu T, Hazlehurst L, Copland JA, Tun HW. A Virtual Screening Platform Identifies Chloroethylagelastatin A as a Potential Ribosomal Inhibitor. Biomolecules. 2020 Oct 5;10(10):1407. doi: 10.3390/biom10101407. PMID: 33027969; PMCID: PMC7599554.


2: Nájera C, Foubelo F, Sansano JM, Yus M. Stereodivergent routes in organic synthesis: marine natural products, lactones, other natural products, heterocycles and unnatural compounds. Org Biomol Chem. 2020 Feb 19;18(7):1279-1336. doi: 10.1039/c9ob02597a. PMID: 32025682.


3: Tsuchimochi I, Kitamura Y, Aoyama H, Akai S, Nakai K, Yoshimitsu T. Total synthesis of (-)-agelastatin A: an SH2' radical azidation strategy. Chem Commun (Camb). 2018 Sep 14;54(71):9893-9896. doi: 10.1039/c8cc05697h. Epub 2018 Aug 7. PMID: 30083679.


4: Sawaki D, Czibik G, Pini M, Ternacle J, Suffee N, Mercedes R, Marcelin G, Surenaud M, Marcos E, Gual P, Clément K, Hue S, Adnot S, Hatem SN, Tsuchimochi I, Yoshimitsu T, Hénégar C, Derumeaux G. Visceral Adipose Tissue Drives Cardiac Aging Through Modulation of Fibroblast Senescence by Osteopontin Production. Circulation. 2018 Aug 21;138(8):809-822. doi: 10.1161/CIRCULATIONAHA.117.031358. PMID: 29500246.


5: Antropow AH, Xu K, Buchsbaum RJ, Movassaghi M. Synthesis and Evaluation of Agelastatin Derivatives as Potent Modulators for Cancer Invasion and Metastasis. J Org Chem. 2017 Aug 4;82(15):7720-7731. doi: 10.1021/acs.joc.7b01162. Epub 2017 Jul 25. PMID: 28696693; PMCID: PMC5600481.


6: Park Y, Liau BB. Uncovering the Cellular Target of Agelastatin A. Cell Chem Biol. 2017 May 18;24(5):542-543. doi: 10.1016/j.chembiol.2017.05.002. PMID: 28525767.


7: McClary B, Zinshteyn B, Meyer M, Jouanneau M, Pellegrino S, Yusupova G, Schuller A, Reyes JCP, Lu J, Guo Z, Ayinde S, Luo C, Dang Y, Romo D, Yusupov M, Green R, Liu JO. Inhibition of Eukaryotic Translation by the Antitumor Natural Product Agelastatin A. Cell Chem Biol. 2017 May 18;24(5):605-613.e5. doi: 10.1016/j.chembiol.2017.04.006. Epub 2017 Apr 27. PMID: 28457705; PMCID: PMC5562292.


8: Lindel T. Chemistry and Biology of the Pyrrole-Imidazole Alkaloids. Alkaloids Chem Biol. 2017;77:117-219. doi: 10.1016/bs.alkal.2016.12.001. Epub 2017 Jan 20. PMID: 28212701.


9: Yoshimitsu T, Tun HW. Compounds, compositions, and methods of agelastatin alkaloids: patent evaluation of WO2015042239 (A1). Expert Opin Ther Pat. 2017 Feb;27(2):113-119. doi: 10.1080/13543776.2017.1273902. Epub 2017 Jan 5. PMID: 28056571.


10: Jouanneau M, McClary B, Reyes JC, Chen R, Chen Y, Plunkett W, Cheng X, Milinichik AZ, Albone EF, Liu JO, Romo D. Derivatization of agelastatin A leading to bioactive analogs and a trifunctional probe. Bioorg Med Chem Lett. 2016 Apr 15;26(8):2092-7. doi: 10.1016/j.bmcl.2016.02.051. Epub 2016 Feb 23. PMID: 26951751; PMCID: PMC5522753.


11: Yoshimitsu T. Endeavors to access molecular complexity: strategic use of free radicals in natural product synthesis. Chem Rec. 2014 Apr;14(2):268-79. doi: 10.1002/tcr.201300024. Epub 2014 Feb 20. PMID: 24677484.


12: Stout EP, Choi MY, Castro JE, Molinski TF. Potent fluorinated agelastatin analogues for chronic lymphocytic leukemia: design, synthesis, and pharmacokinetic studies. J Med Chem. 2014 Jun 26;57(12):5085-93. doi: 10.1021/jm4016922. Epub 2014 Jun 10. PMID: 24673739; PMCID: PMC4079331.


13: Han S, Siegel DS, Morrison KC, Hergenrother PJ, Movassaghi M. Synthesis and anticancer activity of all known (-)-agelastatin alkaloids. J Org Chem. 2013 Dec 6;78(23):11970-84. doi: 10.1021/jo4020112. Epub 2013 Nov 21. PMID: 24152243; PMCID: PMC3920459.


14: Duspara PA, Batey RA. A short total synthesis of the marine sponge pyrrole-2-aminoimidazole alkaloid (±)-agelastatin A. Angew Chem Int Ed Engl. 2013 Oct 4;52(41):10862-6. doi: 10.1002/anie.201304759. Epub 2013 Aug 22. PMID: 24038621.


15: Shigeoka D, Kamon T, Yoshimitsu T. Formal synthesis of (-)-agelastatin A: an iron(II)-mediated cyclization strategy. Beilstein J Org Chem. 2013 May 3;9:860-5. doi: 10.3762/bjoc.9.99. PMID: 23766801; PMCID: PMC3678661.


16: Reyes JC, Romo D. Bioinspired total synthesis of agelastatin A. Angew Chem Int Ed Engl. 2012 Jul 9;51(28):6870-3. doi: 10.1002/anie.201200959. Epub 2012 Jun 11. PMID: 22689447; PMCID: PMC3815442.


17: Kano T, Sakamoto R, Akakura M, Maruoka K. Stereocontrolled synthesis of vicinal diamines by organocatalytic asymmetric Mannich reaction of N-protected aminoacetaldehydes: formal synthesis of (-)-agelastatin A. J Am Chem Soc. 2012 May 2;134(17):7516-20. doi: 10.1021/ja301120z. Epub 2012 Apr 19. PMID: 22486203.


18: Menjo Y, Hamajima A, Sasaki N, Hamada Y. Asymmetric aziridination of cyclic enones using chiral diamine catalysts and its application to the total synthesis of (-)-agelastatin A. Org Lett. 2011 Nov 4;13(21):5744-7. doi: 10.1021/ol2023054. Epub 2011 Oct 3. PMID: 21966984.


19: Movassaghi M, Siegel DS, Han S. Total synthesis of all (-)-Agelastatin alkaloids. Chem Sci. 2010 Jan 1;1:561-566. doi: 10.1039/c0sc00351d. PMID: 21218186; PMCID: PMC3016719.


20: Tilvi S, Moriou C, Martin MT, Gallard JF, Sorres J, Patel K, Petek S, Debitus C, Ermolenko L, Al-Mourabit A. Agelastatin E, agelastatin F, and benzosceptrin C from the marine sponge Agelas dendromorpha. J Nat Prod. 2010 Apr 23;73(4):720-3. doi: 10.1021/np900539j. PMID: 20166736.