Rocaglamide | CAS#84573-16-0 | flavagline

MedKoo Cat#: 406598 | Name: Rocaglamide

Description:

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

Rocaglamide is the first cyclopenta[b]benzofuran derivative (flavagline), isolated from Aglaia elliptifolia in 1982 by King and colleagues based on its antileukemic activity. Like other flavaglines, rocaglamide displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities.

Chemical Structure

Rocaglamide

CAS#84573-16-0

Theoretical Analysis

MedKoo Cat#: 406598

Name: Rocaglamide

CAS#: 84573-16-0

Chemical Formula: C29H31NO7

Exact Mass: 505.2101

Molecular Weight: 505.56

Elemental Analysis: C, 68.90; H, 6.18; N, 2.77; O, 22.15

Price and Availability

Size	Price	Availability
1mg	USD 150.00	Ready to ship
2mg	USD 250.00	Ready to ship
5mg	USD 565.00	Ready to ship
10mg	USD 1,015.00	Ready to ship
25mg	USD 2,285.00	Ready to ship
50mg	USD 4,115.00	Ready to ship

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Synonym

Rocaglamide; Rocaglamide A; RocA; NSC 326408.

IUPAC/Chemical Name

(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxamide

InChi Key

DAPAQENNNINUPW-IDAMAFBJSA-N

InChi Code

InChI=1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1

SMILES Code

O=C([C@H]([C@H]1C2=CC=CC=C2)[C@@H](O)[C@]3(O)[C@@]1(C4=CC=C(OC)C=C4)OC5=CC(OC)=CC(OC)=C35)N(C)C

Appearance

White to off- white 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, not in water

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#BBC60523

QC Data

View QC data: current batch, Lot#BBC60523

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Rocaglamide (RocA) is a heat shock factor 1 (HSF1) activation inhibitor with an IC50 of ~50 nM.

In vitro activity:

This study concludes that combination treatment of rocaglamide and mitomycin C is a highly effective tumor therapy. A low concentration of mitomycin C combined rocaglamide ROC significantly promoted HCT116 and HT29 cell apoptosis and inhibited cell proliferation by downregulating the expression of Bcl-2 and c-FLIP, upregulating the expression of Bax, activating the caspase cascade, arresting cell cycle in G1 phase, and increasing the level of reactive oxygen species. Reference: Pathol Res Pract. 2023 Mar;243:154350. https://pubmed.ncbi.nlm.nih.gov/36780842/

In vivo activity:

In post-heart transplant operated mice, rocaglamide was found to regulate oxidative stress response and reduce inflammatory cell infiltration and organ injury, which have been associated with the inhibition of NF-AT activation in T cells. Reference: Oxid Med Cell Longev. 2022 Jan 17;2022:2048095. https://pubmed.ncbi.nlm.nih.gov/35087613/

	Solvent	mg/mL	mM
Solubility
	DMSO	80.0	158.24
	Ethanol	5.0	9.89

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 505.56 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:

1. Xie L, Cheng L, Wei Y. Mitomycin C enhanced the antitumor efficacy of Rocaglamide in colorectal cancer. Pathol Res Pract. 2023 Mar;243:154350. doi: 10.1016/j.prp.2023.154350. Epub 2023 Feb 4. PMID: 36780842. 2. So L, Obata-Ninomiya K, Hu A, Muir VS, Takamori A, Song J, Buckner JH, Savan R, Ziegler SF. Regulatory T cells suppress CD4+ effector T cell activation by controlling protein synthesis. J Exp Med. 2023 Mar 6;220(3):e20221676. doi: 10.1084/jem.20221676. Epub 2023 Jan 4. PMID: 36598533; PMCID: PMC9827529. 3. Dai C, Zhou X, Wang L, Tan R, Wang W, Yang B, Zhang Y, Shi H, Chen D, Wei L, Chen Z. Rocaglamide Prolonged Allograft Survival by Inhibiting Differentiation of Th1/Th17 Cells in Cardiac Transplantation. Oxid Med Cell Longev. 2022 Jan 17;2022:2048095. doi: 10.1155/2022/2048095. PMID: 35087613; PMCID: PMC8787457. 4. Wu Y, Giaisi M, Köhler R, Chen WM, Krammer PH, Li-Weber M. Rocaglamide breaks TRAIL-resistance in human multiple myeloma and acute T-cell leukemia in vivo in a mouse xenogtraft model. Cancer Lett. 2017 Mar 28;389:70-77. doi: 10.1016/j.canlet.2016.12.010. Epub 2016 Dec 18. PMID: 27998762.

In vitro protocol:

In vivo protocol:

1. Dai C, Zhou X, Wang L, Tan R, Wang W, Yang B, Zhang Y, Shi H, Chen D, Wei L, Chen Z. Rocaglamide Prolonged Allograft Survival by Inhibiting Differentiation of Th1/Th17 Cells in Cardiac Transplantation. Oxid Med Cell Longev. 2022 Jan 17;2022:2048095. doi: 10.1155/2022/2048095. PMID: 35087613; PMCID: PMC8787457. 2. Wu Y, Giaisi M, Köhler R, Chen WM, Krammer PH, Li-Weber M. Rocaglamide breaks TRAIL-resistance in human multiple myeloma and acute T-cell leukemia in vivo in a mouse xenogtraft model. Cancer Lett. 2017 Mar 28;389:70-77. doi: 10.1016/j.canlet.2016.12.010. Epub 2016 Dec 18. PMID: 27998762.

1: Rosenfeld P, Singh G, Paz Herrera A, Ji J, Seufzer B, Heng X, Boris-Lawrie K, Cochrane A. Putting a Kink in HIV-1 Particle Infectivity: Rocaglamide Inhibits HIV-1 Replication by Altering Gag-Genomic RNA Interaction. Viruses. 2024 Sep 23;16(9):1506. doi: 10.3390/v16091506. PMID: 39339982; PMCID: PMC11437399. 2: Oblinger JL, Wang J, Wetherell GD, Agarwal G, Wilson TA, Benson NR, Fenger JM, Fuchs JR, Kinghorn AD, Chang LS. Anti-tumor effects of the eIF4A inhibitor didesmethylrocaglamide and its derivatives in human and canine osteosarcomas. Sci Rep. 2024 Aug 20;14(1):19349. doi: 10.1038/s41598-024-69171-3. PMID: 39164287; PMCID: PMC11335891. 3: Oblinger J, Wang J, Wetherell G, Agarwal G, Wilson T, Benson N, Fenger J, Fuchs J, Kinghorn AD, Chang L. Anti-tumor Effects of the eIF4A Inhibitor Didesmethylrocaglamide and Its Derivatives in Human and Canine Osteosarcomas. Res Sq [Preprint]. 2024 Jun 14:rs.3.rs-4494024. doi: 10.21203/rs.3.rs-4494024/v1. Update in: Sci Rep. 2024 Aug 20;14(1):19349. doi: 10.1038/s41598-024-69171-3. PMID: 38947012; PMCID: PMC11213195. 4: Luo J, Ng W, Liu Y, Wang L, Gong C, Zhou Y, Fang C, Zhu S, Yao C. Rocaglamide promotes infiltration and differentiation of T cells and coordinates with PD-1 inhibitor to overcome checkpoint resistance in multiple tumor models. Cancer Immunol Immunother. 2024 Jun 4;73(8):137. doi: 10.1007/s00262-024-03706-5. PMID: 38833034; PMCID: PMC11150362. 5: Zhu X, Zuo Q, Xie X, Chen Z, Wang L, Chang L, Liu Y, Luo J, Fang C, Che L, Zhou X, Yao C, Gong C, Hu D, Zhao W, Zhou Y, Zhu S. Rocaglamide regulates iron homeostasis by suppressing hepcidin expression. Free Radic Biol Med. 2024 Jul;219:153-162. doi: 10.1016/j.freeradbiomed.2024.04.232. Epub 2024 Apr 23. PMID: 38657753. 6: González-Sánchez AM, Castellanos-Silva EA, Díaz-Figueroa G, Cate JHD. JUN mRNA translation regulation is mediated by multiple 5' UTR and start codon features. PLoS One. 2024 Mar 14;19(3):e0299779. doi: 10.1371/journal.pone.0299779. PMID: 38483896; PMCID: PMC10939236. 7: Kersten R, Trampert DC, Hubers LM, Tolenaars D, Vos HR, van de Graaf SFJ, Beuers U. Galectin-3 and prohibitin 1 are autoantigens in IgG4-related cholangitis without clear-cut protective effects against toxic bile acids. Front Immunol. 2024 Jan 25;14:1251134. doi: 10.3389/fimmu.2023.1251134. PMID: 38332916; PMCID: PMC10851949. 8: Longevity OMAC. Retracted: Rocaglamide Prolonged Allograft Survival by Inhibiting Differentiation of Th1/Th17 Cells in Cardiac Transplantation. Oxid Med Cell Longev. 2024 Jan 9;2024:9810207. doi: 10.1155/2024/9810207. PMID: 38234533; PMCID: PMC10791476. 9: González-Sánchez AM, Castellanos-Silva EA, Díaz-Figueroa G, Cate JHD. JUN mRNA Translation Regulation is Mediated by Multiple 5' UTR and Start Codon Features. bioRxiv [Preprint]. 2023 Nov 17:2023.11.17.567602. doi: 10.1101/2023.11.17.567602. Update in: PLoS One. 2024 Mar 14;19(3):e0299779. doi: 10.1371/journal.pone.0299779. PMID: 38014201; PMCID: PMC10680820. 10: Saini M, Ngwa CJ, Marothia M, Verma P, Ahmad S, Kumari J, Anand S, Vandana V, Goyal B, Chakraborti S, Pandey KC, Garg S, Pati S, Ranganathan A, Pradel G, Singh S. Characterization of Plasmodium falciparum prohibitins as novel targets to block infection in humans by impairing the growth and transmission of the parasite. Biochem Pharmacol. 2023 Jun;212:115567. doi: 10.1016/j.bcp.2023.115567. Epub 2023 Apr 22. PMID: 37088154. 11: Xie L, Cheng L, Wei Y. Mitomycin C enhanced the antitumor efficacy of Rocaglamide in colorectal cancer. Pathol Res Pract. 2023 Mar;243:154350. doi: 10.1016/j.prp.2023.154350. Epub 2023 Feb 4. PMID: 36780842. 12: Li F, Fang J, Yu Y, Hao S, Zou Q, Zeng Q, Yang X. Reanalysis of ribosome profiling datasets reveals a function of rocaglamide A in perturbing the dynamics of translation elongation via eIF4A. Nat Commun. 2023 Feb 2;14(1):553. doi: 10.1038/s41467-023-36290-w. PMID: 36725859; PMCID: PMC9891901. 13: So L, Obata-Ninomiya K, Hu A, Muir VS, Takamori A, Song J, Buckner JH, Savan R, Ziegler SF. Regulatory T cells suppress CD4+ effector T cell activation by controlling protein synthesis. J Exp Med. 2023 Mar 6;220(3):e20221676. doi: 10.1084/jem.20221676. Epub 2023 Jan 4. PMID: 36598533; PMCID: PMC9827529. 14: Abdelkrim YZ, Harigua-Souiai E, Bassoumi-Jamoussi I, Barhoumi M, Banroques J, Essafi-Benkhadir K, Nilges M, Blondel A, Tanner NK, Guizani I. Enzymatic and Molecular Characterization of Anti-Leishmania Molecules That Differently Target Leishmania and Mammalian eIF4A Proteins, LieIF4A and eIF4AMus. Molecules. 2022 Sep 10;27(18):5890. doi: 10.3390/molecules27185890. PMID: 36144626; PMCID: PMC9502374. 15: Pedroni L, Dellafiora L, Varrà MO, Galaverna G, Ghidini S. In silico study on the Hepatitis E virus RNA Helicase and its inhibition by silvestrol, rocaglamide and other flavagline compounds. Sci Rep. 2022 Sep 15;12(1):15512. doi: 10.1038/s41598-022-19818-w. PMID: 36109625; PMCID: PMC9477874. 16: Kayastha F, Herrington NB, Kapadia B, Roychowdhury A, Nanaji N, Kellogg GE, Gartenhaus RB. Novel eIF4A1 inhibitors with anti-tumor activity in lymphoma. Mol Med. 2022 Sep 4;28(1):101. doi: 10.1186/s10020-022-00534-0. PMID: 36058921; PMCID: PMC9441068. 17: Dos Santos IVF, Borges RS, Silva GM, de Lima LR, Bastos RS, Ramos RS, Silva LB, da Silva CHTP, Dos Santos CBR. Hierarchical Virtual Screening Based on Rocaglamide Derivatives to Discover New Potential Anti-Skin Cancer Agents. Front Mol Biosci. 2022 Jun 2;9:836572. doi: 10.3389/fmolb.2022.836572. PMID: 35720115; PMCID: PMC9201829. 18: Ha YS, Kim TK, Park KS, Hwang S, Kim J, Kim SJ. Inhibitory effects of Rocaglamide-A on PPARγ-driven adipogenesis through regulation of mitotic clonal expansion involving the JAK2/STAT3 pathway. Biochim Biophys Acta Mol Cell Biol Lipids. 2022 Jun;1867(6):159148. doi: 10.1016/j.bbalip.2022.159148. Epub 2022 Mar 3. PMID: 35248800. 19: Wu PF, Liu J, Li YN, Ding R, Tan R, Yang XM, Yu Y, Hao XJ, Yuan CM, Yi P. Three New Aglain Derivatives from Aglaia odorata Lour. and Their Cytotoxic Activities. Chem Biodivers. 2022 Apr;19(4):e202101008. doi: 10.1002/cbdv.202101008. Epub 2022 Mar 8. PMID: 35194923. 20: Dai C, Zhou X, Wang L, Tan R, Wang W, Yang B, Zhang Y, Shi H, Chen D, Wei L, Chen Z. Rocaglamide Prolonged Allograft Survival by Inhibiting Differentiation of Th1/Th17 Cells in Cardiac Transplantation. Oxid Med Cell Longev. 2022 Jan 17;2022:2048095. doi: 10.1155/2022/2048095. Retraction in: Oxid Med Cell Longev. 2024 Jan 9;2024:9810207. doi: 10.1155/2024/9810207. PMID: 35087613; PMCID: PMC8787457.