WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H333105
CAS#: 693778-57-3
Description: Verticilide is a new ryanodine-binding inhibitor. Verticilide, was isolated from the cultured broth of a fungus, Verticillium sp. FKI-1033. It is a 24-membered ring cyclic depsipeptide, its structure being elucidated as cyclo[(2R)-2-hydroxyheptanoyl-N-methyl- L-alanyl](4). Verticilide inhibited ryanodine binding to ryanodine receptors in the cockroach at an IC(50) value of 4.2 microM, whereas inhibition against mouse ryanodine receptors was weak (IC(50)=53.9 microM).
Hodoodo Cat#: H333105
Name: Verticilide
CAS#: 693778-57-3
Chemical Formula: C44H76N4O12
Exact Mass: 852.55
Molecular Weight: 853.110
Elemental Analysis: C, 61.95; H, 8.98; N, 6.57; O, 22.50
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Related CAS #: 2056011-05-1 (Ent-isomer) 693778-57-3
Synonym: FKI 1033; FKI-1033; FKI-1033; Verticilide ; Verticilide A 1;
IUPAC/Chemical Name: (3S,6R,9S,12R,15S,18R,21S,24R)-3,4,9,10,15,16,21,22-octamethyl-6,12,18,24-tetrapentyl-1,7,13,19-tetraoxa-4,10,16,22-tetraazacyclotetracosan-2,5,8,11,14,17,20,23-octaone
InChi Key: CMEGQABRBDDBTQ-NQRIZWSQSA-N
InChi Code: InChI=1S/C44H76N4O12/c1-13-17-21-25-33-37(49)45(9)30(6)42(54)58-35(27-23-19-15-3)39(51)47(11)32(8)44(56)60-36(28-24-20-16-4)40(52)48(12)31(7)43(55)59-34(26-22-18-14-2)38(50)46(10)29(5)41(53)57-33/h29-36H,13-28H2,1-12H3/t29-,30-,31-,32-,33+,34+,35+,36+/m0/s1
SMILES Code: C(CCCC)[C@@H]1C(=O)N(C)[C@@H](C)C(=O)O[C@H](CCCCC)C(=O)N(C)[C@@H](C)C(=O)O[C@H](CCCCC)C(=O)N(C)[C@@H](C)C(=O)O[C@H](CCCCC)C(=O)N(C)[C@@H](C)C(=O)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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 853.11 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: |
1: Gochman A, Do TQ, Kim K, Schwarz JA, Thorpe MP, Blackwell DJ, Smith AN, Akers WS, Cornea RL, Laver DR, Johnston JN, Knollmann BC. ent -Verticilide B1 inhibits type 2 ryanodine receptor channels and is antiarrhythmic in Casq2-/- mice. bioRxiv [Preprint]. 2023 Jul 5:2023.07.03.547578. doi: 10.1101/2023.07.03.547578. PMID: 37461611; PMCID: PMC10349981.
2: Kim K, Blackwell DJ, Yuen SL, Thorpe MP, Johnston JN, Cornea RL, Knollmann BC. The selective RyR2 inhibitor ent-verticilide suppresses atrial fibrillation susceptibility caused by Pitx2 deficiency. J Mol Cell Cardiol. 2023 Jul;180:1-9. doi: 10.1016/j.yjmcc.2023.04.005. Epub 2023 Apr 18. PMID: 37080450; PMCID: PMC10330243.
3: Blackwell DJ, Smith AN, Do T, Gochman A, Schmeckpeper J, Hopkins CR, Akers WS, Johnston JN, Knollmann BC. In Vivo Pharmacokinetic and Pharmacodynamic Properties of the Antiarrhythmic Molecule ent-Verticilide. J Pharmacol Exp Ther. 2023 Jun;385(3):205-213. doi: 10.1124/jpet.122.001455. Epub 2023 Mar 9. PMID: 36894328; PMCID: PMC10201578.
4: Smith AN, Thorpe MP, Blackwell DJ, Batiste SM, Hopkins CR, Schley ND, Knollmann BC, Johnston JN. Structure-Activity Relationships for the N-Me- Versus N-H-Amide Modification to Macrocyclic ent-Verticilide Antiarrhythmics. ACS Med Chem Lett. 2022 Oct 5;13(11):1755-1762. doi: 10.1021/acsmedchemlett.2c00377. PMID: 36385927; PMCID: PMC9661706.
5: Smith AN, Blackwell DJ, Knollmann BC, Johnston JN. Ring Size as an Independent Variable in Cyclooligomeric Depsipeptide Antiarrhythmic Activity. ACS Med Chem Lett. 2021 Nov 23;12(12):1942-1947. doi: 10.1021/acsmedchemlett.1c00508. PMID: 34917258; PMCID: PMC8667307.
6: Batiste SM, Blackwell DJ, Kim K, Kryshtal DO, Gomez-Hurtado N, Rebbeck RT, Cornea RL, Johnston JN, Knollmann BC. Unnatural verticilide enantiomer inhibits type 2 ryanodine receptor-mediated calcium leak and is antiarrhythmic. Proc Natl Acad Sci U S A. 2019 Mar 12;116(11):4810-4815. doi: 10.1073/pnas.1816685116. Epub 2019 Feb 21. PMID: 30792355; PMCID: PMC6421472.
7: D'Amato A, Della Sala G, Izzo I, Costabile C, Masuda Y, De Riccardis F. Cyclic Octamer Peptoids: Simplified Isosters of Bioactive Fungal Cyclodepsipeptides. Molecules. 2018 Jul 19;23(7):1779. doi: 10.3390/molecules23071779. PMID: 30029532; PMCID: PMC6100324.
8: Ohshiro T, Matsuda D, Kazuhiro T, Uchida R, Nonaka K, Masuma R, Tomoda H. New verticilides, inhibitors of acyl-CoA:cholesterol acyltransferase, produced by Verticillium sp. FKI-2679. J Antibiot (Tokyo). 2012 May;65(5):255-62. doi: 10.1038/ja.2012.12. Epub 2012 Mar 14. PMID: 22415459.
9: Lüttenberg S, Sondermann F, Scherkenbeck J. Anthelmintic PF1022A: stepwise solid-phase synthesis of a cyclodepsipeptide containing N-methyl amino acids. Tetrahedron. 2012 Feb 25;68(8):2068-2073. doi: 10.1016/j.tet.2011.12.026. Epub 2011 Dec 16. PMID: 32287426; PMCID: PMC7111844.
10: Shiomi K, Matsui R, Kakei A, Yamaguchi Y, Masuma R, Hatano H, Arai N, Isozaki M, Tanaka H, Kobayashi S, Turberg A, Omura S. Verticilide, a new ryanodine-binding inhibitor, produced by Verticillium sp. FKI-1033. J Antibiot (Tokyo). 2010 Feb;63(2):77-82. doi: 10.1038/ja.2009.126. Epub 2010 Jan 8. PMID: 20057513.
11: Monma S, Sunazuka T, Nagai K, Arai T, Shiomi K, Matsui R, Omura S. Verticilide: elucidation of absolute configuration and total synthesis. Org Lett. 2006 Nov 23;8(24):5601-4. doi: 10.1021/ol0623365. PMID: 17107082.
