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MedKoo Cat#: 531791 | Name: FR900359
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Description:

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

FR900359 is a cyclic depsipeptide that has been found in A. crenata. FR900359 is a potent and selective inhibitors of the Gq/11-signaling pathway. It induces cell cycle arrest at the G1 phase and reduces proliferation and serum-induced migration of B16 melanoma cells. FR900359 inhibits airway hyperresponsiveness in a mouse model of house dust mite-induced allergic asthma. Note; This product is supplied as a solution in acetonitrile.

Chemical Structure

FR900359
FR900359
CAS#107530-18-7

Theoretical Analysis

MedKoo Cat#: 531791

Name: FR900359

CAS#: 107530-18-7

Chemical Formula: C49H75N7O15

Exact Mass: 1001.5321

Molecular Weight: 1002.17

Elemental Analysis: C, 58.73; H, 7.54; N, 9.78; O, 23.95

Price and Availability

Size Price Availability Quantity
1mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
FR900359; FR 900359; FR-900359; UBO-QIC;
IUPAC/Chemical Name
[(1R)-1-[(3S,6S,9S,12S,18R,21S,22R)-21-acetamido-18-benzyl-3-[(1R)-1-methoxyethyl]-4,9,10,12,16-pentamethyl-15-methylidene-2,5,8,11,14,17,20-heptaoxo-22-propan-2-yl-1,19-dioxa-4,7,10,13,16-pentazacyclodocos-6-yl]-2-methylpropyl] (2S,3R)-3-hydroxy-4-methyl-2-(propanoylamino)pentanoate
InChi Key
IMXKHFILKMPFGB-ZWYWTTNJSA-N
InChi Code
InChI=1S/C49H75N7O15/c1-17-34(58)52-35(39(59)24(2)3)47(65)70-40(25(4)5)36-46(64)56(15)38(30(11)68-16)49(67)71-41(26(6)7)37(51-31(12)57)48(66)69-33(23-32-21-19-18-20-22-32)45(63)55(14)28(9)42(60)50-27(8)44(62)54(13)29(10)43(61)53-36/h18-22,24-27,29-30,33,35-41,59H,9,17,23H2,1-8,10-16H3,(H,50,60)(H,51,57)(H,52,58)(H,53,61)/t27-,29-,30+,33+,35-,36-,37-,38-,39+,40+,41+/m0/s1
SMILES Code
CC(C)[C@@H](O)[C@H](NC(CC)=O)C(O[C@@H]([C@H](NC([C@H](C)N(C)C([C@H](C)NC(C(N(C)C([C@@H](CC1=CC=CC=C1)O2)=O)=C)=O)=O)=O)C(N(C)[C@@H]([C@H](OC)C)C(O[C@H](C(C)C)[C@H](NC(C)=O)C2=O)=O)=O)C(C)C)=O
Appearance
A solution in acetonitrile.
Purity
>95% (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
The cyclic depsipeptide FR900359 (FR) is derived from the soil bacterium Chromobacterium vaccinii and known to bind Gq proteins of mammals and insects, thereby abolishing the signal transduction of their Gq protein-coupled receptors, a process that leads to severe physiological consequences. Due to their highly conserved structure, Gq family of proteins are a superior ecological target for FR producing organisms, resulting in a defense towards a broad range of harmful organisms.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,002.17 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
1: Hashimoto T, Suenaga H, Amagai K, Hashimoto J, Kozone I, Takahashi S, Shin-Ya K. In Vitro Module Editing Of NRPS Enables Production Of Highly Potent Gq -Signaling Inhibitor FR900359 Derived From Unculturable Plant Symbiont. Angew Chem Int Ed Engl. 2024 Mar 4;63(10):e202317805. doi: 10.1002/anie.202317805. Epub 2024 Feb 2. PMID: 38238265. 2: Zhu Y, Liu S, Zigmond J, Kaltenbronn KM, Blumer KJ, Moeller KD. A Building Block Approach for the Total Synthesis of YM-385781. European J Org Chem. 2023 May 22;26(20):e202300365. doi: 10.1002/ejoc.202300365. Epub 2023 Apr 25. PMID: 38188369; PMCID: PMC10766104. 3: Voss JH. Recommended Tool Compounds: Application of YM-254890 and FR900359 to Interrogate Gαq/11-Mediated Signaling Pathways. ACS Pharmacol Transl Sci. 2023 Nov 10;6(12):1790-1800. doi: 10.1021/acsptsci.3c00214. PMID: 38093837; PMCID: PMC10714435. 4: Onken MD, Erdmann-Gilmore P, Zhang Q, Thapa K, King E, Kaltenbronn KM, Noda SE, Makepeace CM, Goldfarb D, Babur Ö, Townsend RR, Blumer KJ. Protein Kinase Signaling Networks Driven by Oncogenic Gq/11 in Uveal Melanoma Identified by Phosphoproteomic and Bioinformatic Analyses. Mol Cell Proteomics. 2023 Nov;22(11):100649. doi: 10.1016/j.mcpro.2023.100649. Epub 2023 Sep 19. PMID: 37730182; PMCID: PMC10616553. 5: Johnson ET, Bowman MJ, Gomes RP, Carneiro LC, Dunlap CA. Identification of 2,4-diacetylphloroglucinol production in the genus Chromobacterium. Sci Rep. 2023 Aug 31;13(1):14292. doi: 10.1038/s41598-023-41277-0. PMID: 37653049; PMCID: PMC10471698. 6: Hanke W, Alenfelder J, Liu J, Gutbrod P, Kehraus S, Crüsemann M, Dörmann P, Kostenis E, Scholz M, König GM. The Bacterial Gq Signal Transduction Inhibitor FR900359 Impairs Soil-Associated Nematodes. J Chem Ecol. 2023 Oct;49(9-10):549-569. doi: 10.1007/s10886-023-01442-1. Epub 2023 Jul 15. PMID: 37453001; PMCID: PMC10725363. 7: Wirtz DA, Schneberger N, Klöppel S, Richarz R, Geyer M, König GM, Hagelueken G, Crüsemann M. Adenylation Domain-Guided Recruitment of Trans-Acting Nonheme Monooxygenases in Nonribosomal Peptide Biosynthesis. ACS Chem Biol. 2023 Aug 18;18(8):1748-1759. doi: 10.1021/acschembio.3c00106. Epub 2023 Jun 27. PMID: 37366538. 8: Lorza-Gil E, Kaiser G, Carlein C, Hoffmann MDA, König GM, Haug S, Prates Roma L, Rexen Ulven E, Ulven T, Kostenis E, Birkenfeld AL, Häring HU, Ullrich S, Gerst F. Glucose-stimulated insulin secretion depends on FFA1 and Gq in neonatal mouse islets. Diabetologia. 2023 Aug;66(8):1501-1515. doi: 10.1007/s00125-023-05932-5. Epub 2023 May 23. PMID: 37217659; PMCID: PMC10317898. 9: Voss JH, Crüsemann M, Bartling CRO, Kehraus S, Inoue A, König GM, Strømgaard K, Müller CE. Structure-affinity and structure-residence time relationships of macrocyclic Gαq protein inhibitors. iScience. 2023 Mar 23;26(4):106492. doi: 10.1016/j.isci.2023.106492. PMID: 37091255; PMCID: PMC10119753. 10: Pistorius D, Buntin K, Richard E, Rust M, Bouquet C, Wollbrett S, Weber E, Dietschin D, Bruccoleri R, Oakeley E, Petersen F. Valhidepsin Lipopeptides from Chromobacterium vaccinii: Structures, Biosynthesis, and Coregulation with FR900359 Production. J Nat Prod. 2023 Feb 24;86(2):246-255. doi: 10.1021/acs.jnatprod.2c00825. Epub 2023 Feb 6. PMID: 36745695. 11: Voss JH, Al-Hroub H, Gedschold R, Dietrich JM, Gaffal E, Toma M, Kehraus S, König GM, Brust P, Fleischmann BK, Wenzel D, Deuther-Conrad W, Müller CE. Imaging of Gαq Proteins in Mouse and Human Organs and Tissues. Pharmaceutics. 2022 Dec 24;15(1):57. doi: 10.3390/pharmaceutics15010057. PMID: 36678686; PMCID: PMC9865079. 12: Medcalf MR, Krueger RL, Medcalf ZT, Rosston PA, Zhu Y, Kaltenbronn KM, Blumer KJ, Moeller KD. Building Chemical Probes Based on the Natural Products YM-254890 and FR900359: Advances toward Scalability. Synthesis (Stuttg). 2023 Jan;55(1):90-106. doi: 10.1055/a-1873-6891. Epub 2022 Oct 6. PMID: 36644007; PMCID: PMC9838186. 13: Kamato D, Gabr M, Kumarapperuma H, Chia ZJ, Zheng W, Xu S, Osman N, Little PJ. Gαq Is the Specific Mediator of PAR-1 Transactivation of Kinase Receptors in Vascular Smooth Muscle Cells. Int J Mol Sci. 2022 Nov 20;23(22):14425. doi: 10.3390/ijms232214425. PMID: 36430902; PMCID: PMC9692893. 14: Niu Y, Wang K, Zhu X, Zhang S, Cherepanoff S, Conway RM, Madigan MC, Lim LA, Zhu L, Murray M, Zhou F. The application of natural compounds in uveal melanoma drug discovery. J Pharm Pharmacol. 2022 May 20;74(5):660-680. doi: 10.1093/jpp/rgac009. PMID: 35532546. 15: Voss JH, Müller CE. Heterotrimeric G Protein α-Subunits - Structures, Peptide-Derived Inhibitors, and Mechanisms. Curr Med Chem. 2022;29(42):6359-6378. doi: 10.2174/0929867329666220308112424. PMID: 35260051. 16: Cui Y, Kassmann M, Nickel S, Zhang C, Alenina N, Anistan YM, Schleifenbaum J, Bader M, Welsh DG, Huang Y, Gollasch M. Myogenic Vasoconstriction Requires Canonical Gq/11 Signaling of the Angiotensin II Type 1 Receptor. J Am Heart Assoc. 2022 Feb 15;11(4):e022070. doi: 10.1161/JAHA.121.022070. Epub 2022 Feb 8. PMID: 35132870; PMCID: PMC9245832. 17: Onken MD, Noda SE, Kaltenbronn KM, Frankfater C, Makepeace CM, Fettig N, Piggott KD, Custer PL, Ippolito JE, Blumer KJ. Oncogenic Gq/11 signaling acutely drives and chronically sustains metabolic reprogramming in uveal melanoma. J Biol Chem. 2022 Jan;298(1):101495. doi: 10.1016/j.jbc.2021.101495. Epub 2021 Dec 14. PMID: 34919964; PMCID: PMC8761705. 18: Pistorius D, Buntin K, Weber E, Richard E, Bouquet C, Wollbrett S, Regenass H, Peón V, Böhm M, Kessler R, Gempeler T, Haberkorn A, Wimmer L, Lanshoeft C, Davis J, Hainzl D, D'Alessio JA, Manchado E, Petersen F. Promoter-Driven Overexpression in Chromobacterium vaccinii Facilitates Access to FR900359 and Yields Novel Low Abundance Analogs. Chemistry. 2022 Feb 7;28(8):e202103888. doi: 10.1002/chem.202103888. Epub 2021 Dec 28. PMID: 34878202. 19: Klöppel S, Richarz R, Wirtz DA, Vasenda N, König GM, Crüsemann M. A Specialized Dehydrogenase Provides l-Phenyllactate for FR900359 Biosynthesis. Chembiochem. 2022 May 18;23(10):e202100569. doi: 10.1002/cbic.202100569. Epub 2021 Dec 9. PMID: 34846772; PMCID: PMC9299796. 20: Voss JH, Nagel J, Rafehi M, Guixà-González R, Malfacini D, Patt J, Kehraus S, Inoue A, König GM, Kostenis E, Deupi X, Namasivayam V, Müller CE. Unraveling binding mechanism and kinetics of macrocyclic Gαq protein inhibitors. Pharmacol Res. 2021 Nov;173:105880. doi: 10.1016/j.phrs.2021.105880. Epub 2021 Sep 17. PMID: 34506902.

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AZD6642

AZD6642