Avrainvillamide | CAS#269741-97-1 | Cancer cell growth inhibitor

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

MedKoo CAT#: 464405

CAS#: 269741-97-1

Description: Avrainvillamide is a fungal metabolite and monomeric form of stephacidin B that has been found in A. ochraceus. It is active against S. aureus, S. pyogenes, and E. faecalis (MICs = 12.5, 12.5, and 25 µg/ml, respectively). Avrainvillamide inhibits the growth of LNCaP, BT-549, T47D, and MALME-3M cancer cells with GI50 values of 0.24, 0.62, 0.21, and 0.41 µM, respectively.

Chemical Structure

Avrainvillamide

CAS# 269741-97-1

Instruction

Theoretical Analysis

MedKoo Cat#: 464405
Name: Avrainvillamide
CAS#: 269741-97-1
Chemical Formula: C26H27N3O4
Exact Mass: 445.20
Molecular Weight: 445.519
Elemental Analysis: C, 70.09; H, 6.11; N, 9.43; O, 14.36

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 1050	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Avrainvillamide; CJ-17,665; CJ17,665; CJ 17,665;

IUPAC/Chemical Name: (7aS,13aS)-3,3,14,14-tetramethyl-8,16-dioxo-3,11,12,13,13a,14-hexahydro-8H,10H-7a,12a-(epiminomethano)indolizino[6,7-h]pyrano[3,2-a]carbazole 15-oxide

InChi Key: ALXLLOQTGLPCFG-XLXODUMSSA-N

InChi Code: InChI=1S/C26H27N3O4/c1-23(2)10-8-15-17(33-23)7-6-14-16-12-26-18(24(3,4)20(16)29(32)19(14)15)13-25(21(30)27-26)9-5-11-28(25)22(26)31/h6-8,10,12,18H,5,9,11,13H2,1-4H3,(H,27,30)/t18-,25?,26-/m0/s1

SMILES Code: O=C1[C@]2(NC3=O)C=C(C=4C(C)(C)[C@@]2(CC35N1CCC5)[H])C6=CC=C7C(C=CC(C)(O7)C)=C6N4=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: 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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 445.52 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.

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: Ranieri R, Pianigiani G, Sciabolacci S, Perriello VM, Marra A, Cardinali V, Pierangeli S, Milano F, Gionfriddo I, Brunetti L, Martelli MP, Falini B. Current status and future perspectives in targeted therapy of NPM1-mutated AML. Leukemia. 2022 Oct;36(10):2351-2367. doi: 10.1038/s41375-022-01666-2. Epub 2022 Aug 25. PMID: 36008542; PMCID: PMC9522592.

2: Nising CF. Recent synthetic approaches towards the antiproliferative natural products avrainvillamide and stephacidin B. Chem Soc Rev. 2010 Feb;39(2):591-9. doi: 10.1039/b900407f. Epub 2009 Dec 14. PMID: 20111783.

3: Wulff JE, Siegrist R, Myers AG. The natural product avrainvillamide binds to the oncoprotein nucleophosmin. J Am Chem Soc. 2007 Nov 21;129(46):14444-51. doi: 10.1021/ja075327f. Epub 2007 Oct 25. PMID: 17958425; PMCID: PMC2557551.

4: Mukherjee H, Chan KP, Andresen V, Hanley ML, Gjertsen BT, Myers AG. Interactions of the natural product (+)-avrainvillamide with nucleophosmin and exportin-1 Mediate the cellular localization of nucleophosmin and its AML- associated mutants. ACS Chem Biol. 2015 Mar 20;10(3):855-63. doi: 10.1021/cb500872g. Epub 2015 Jan 5. PMID: 25531824; PMCID: PMC4652655.

5: Mikkola R, Andersson MA, Hautaniemi M, Salkinoja-Salonen MS. Toxic indole alkaloids avrainvillamide and stephacidin B produced by a biocide tolerant indoor mold Aspergillus westerdijkiae. Toxicon. 2015 Jun 1;99:58-67. doi: 10.1016/j.toxicon.2015.03.011. Epub 2015 Mar 21. PMID: 25804991.

6: Baran PS, Hafensteiner BD, Ambhaikar NB, Guerrero CA, Gallagher JD. Enantioselective total synthesis of avrainvillamide and the stephacidins. J Am Chem Soc. 2006 Jul 5;128(26):8678-93. doi: 10.1021/ja061660s. PMID: 16802835.

7: Andresen V, Erikstein BS, Mukherjee H, Sulen A, Popa M, Sørnes S, Reikvam H, Chan KP, Hovland R, McCormack E, Bruserud Ø, Myers AG, Gjertsen BT. Anti- proliferative activity of the NPM1 interacting natural product avrainvillamide in acute myeloid leukemia. Cell Death Dis. 2016 Dec 1;7(12):e2497. doi: 10.1038/cddis.2016.392. PMID: 27906185; PMCID: PMC5260983.

8: Wulff JE, Herzon SB, Siegrist R, Myers AG. Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell culture. J Am Chem Soc. 2007 Apr 25;129(16):4898-9. doi: 10.1021/ja0690971. Epub 2007 Mar 31. PMID: 17397160; PMCID: PMC3175819.

9: Meng Q, Li BX, Xiao X. Toward Developing Chemical Modulators of Hsp60 as Potential Therapeutics. Front Mol Biosci. 2018 Apr 20;5:35. doi: 10.3389/fmolb.2018.00035. PMID: 29732373; PMCID: PMC5920047.

10: Myers AG, Herzon SB. Identification of a novel Michael acceptor group for the reversible addition of oxygen- and sulfur-based nucleophiles. Synthesis and reactivity of the 3-alkylidene-3H-indole 1-oxide function of avrainvillamide. J Am Chem Soc. 2003 Oct 8;125(40):12080-1. doi: 10.1021/ja0372006. PMID: 14518979.

11: Escolano C. Stephacidin B, the avrainvillamide dimer: a formidable synthetic challenge. Angew Chem Int Ed Engl. 2005 Dec 2;44(47):7670-3. doi: 10.1002/anie.200502383. PMID: 16252300.

12: Baran PS, Guerrero CA, Hafensteiner BD, Ambhaikar NB. Total synthesis of avrainvillamide (CJ-17,665) and stephacidin B. Angew Chem Int Ed Engl. 2005 Jun 20;44(25):3892-5. doi: 10.1002/anie.200500655. PMID: 15900526.

13: Newmister SA, Gober CM, Romminger S, Yu F, Tripathi A, Parra LL, Williams RM, Berlinck RG, Joullié MM, Sherman DH. OxaD: A Versatile Indolic Nitrone Synthase from the Marine-Derived Fungus Penicillium oxalicum F30. J Am Chem Soc. 2016 Sep 7;138(35):11176-84. doi: 10.1021/jacs.6b04915. Epub 2016 Aug 24. PMID: 27505044; PMCID: PMC5014723.

14: Suo L, Dai W, Qin X, Li G, Zhang D, Cheng T, Yao T, Zhang C. Screening of primary open-angle glaucoma diagnostic markers based on immune-related genes and immune infiltration. BMC Genom Data. 2022 Aug 24;23(1):67. doi: 10.1186/s12863-022-01072-8. PMID: 36002796; PMCID: PMC9400315.

15: Mukai K, de Sant'Ana DP, Hirooka Y, Mercado-Marin EV, Stephens DE, Kou KGM, Richter SC, Kelley N, Sarpong R. Bioinspired chemical synthesis of monomeric and dimeric stephacidin A congeners. Nat Chem. 2018 Jan;10(1):38-44. doi: 10.1038/nchem.2862. Epub 2017 Sep 18. PMID: 29256515; PMCID: PMC6317722.

16: Herzon SB, Myers AG. Enantioselective synthesis of stephacidin B. J Am Chem Soc. 2005 Apr 20;127(15):5342-4. doi: 10.1021/ja0510616. PMID: 15826171.

17: Hafensteiner BD, Escribano M, Petricci E, Baran PS. An improved synthesis of alpha,beta-unsaturated nitrones relevant to the stephacidins and analogs thereof. Bioorg Med Chem Lett. 2009 Jul 15;19(14):3808-10. doi: 10.1016/j.bmcl.2009.04.045. Epub 2009 Apr 18. PMID: 19423345; PMCID: PMC2709696.

18: Shenvi RA, O'Malley DP, Baran PS. Chemoselectivity: the mother of invention in total synthesis. Acc Chem Res. 2009 Apr 21;42(4):530-41. doi: 10.1021/ar800182r. PMID: 19182997; PMCID: PMC2765532.

19: Greshock TJ, Grubbs AW, Tsukamoto S, Williams RM. A concise, biomimetic total synthesis of stephacidin A and notoamide B. Angew Chem Int Ed Engl. 2007;46(13):2262-5. doi: 10.1002/anie.200604378. PMID: 17304610.

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