Radicicol | CAS#12772-57-5 | Hsp90 N-terminal inhibitor

MedKoo Cat#: 562206 | Name: Radicicol

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Description:

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

Radicicol is an Hsp90 N-terminal inhibitor and LKB1 destabilizer. Radicicol is an anti-two-component system (TCS) medication. Radicicol decreases photosynthetic efficiency, mainly by inhibiting the electron transport efficiency of the PSII acceptor side and the activity of the PSII reaction centers.

Chemical Structure

Radicicol

CAS#12772-57-5

Theoretical Analysis

MedKoo Cat#: 562206

Name: Radicicol

CAS#: 12772-57-5

Chemical Formula: C18H17ClO6

Exact Mass: 364.0714

Molecular Weight: 364.78

Elemental Analysis: C, 59.27; H, 4.70; Cl, 9.72; O, 26.32

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 220.00	2 Weeks
5mg	USD 600.00	2 Weeks

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Synonym

Radicicol; Monorden;

IUPAC/Chemical Name

(1aR,2Z,4E,14S,15aR)-8-Chloro-9,11-dihydroxy-14-methyl-1a,14,15,15a-tetrahydro-6H-benzo[c]oxireno[2,3-k][1]oxacyclotetradecine-6,12(7H)-dione

InChi Key

WYZWZEOGROVVHK-RFVWBQTHSA-N

InChi Code

InChI=1S/C18H17ClO6/c1-9-6-15-14(25-15)5-3-2-4-10(20)7-11-16(18(23)24-9)12(21)8-13(22)17(11)19/h2-5,8-9,14-15,21-22H,6-7H2,1H3/b4-2+,5-3-/t9-,14+,15+/m0/s1

SMILES Code

O=C1CC2=C(Cl)C(O)=CC(O)=C2C(O[C@@H](C)C[C@]3([H])[C@@](O3)([H])/C=C\C=C\1)=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

Soluble in ethanol

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in ethanol

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

Instruction

View handling instruction

Biological target:

Radicicol is an antifungal antibiotic. It inhibits heat shock protein 90 (Hsp90) activity by binding to the ATP-binding pocket, subsequently suppressing cell transformation induced by src, ras and mos. Radicicol represses estrogen receptor transcriptional activity and inhibits angiogenesis.\

In vitro activity:

Radicicol induces cell death mediated through PI3K/Akt signaling with modulation of hsp90 client proteins and hsp70 inhibition enhances radicicol-induced cell death with suppression of survivin in anaplastic thyroid carcinomacells. Reference: Anticancer Res. 2014 Sep;34(9):4829-37. https://pubmed.ncbi.nlm.nih.gov/25202064/

In vivo activity:

Radicicol decreased photosynthetic efficiency of Chlamydomonas reinhardtii, mainly by inhibiting the electron transport efficiency of the PSII acceptor side and the activity of the PSII reaction centers. Radicicol reduced the primary photochemical reaction efficiency and antenna size. These findings provide new ideas for the design of novel and efficient herbicide molecules. Reference: Plants (Basel). 2023 Feb 2;12(3):665. https://pubmed.ncbi.nlm.nih.gov/36771749/

	Solvent	mg/mL	mM
Solubility
	Ethanol	3.7	10.00

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 364.78 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. Kim SH, Kang JG, Kim CS, Ihm SH, Choi MG, Yoo HJ, Lee SJ. Hsp70 inhibition potentiates radicicol-induced cell death in anaplastic thyroid carcinoma cells. Anticancer Res. 2014 Sep;34(9):4829-37. PMID: 25202064. 2. Qin F, Li Y, Lin R, Zhang X, Mao Z, Ling J, Yang Y, Zhuang X, Du S, Cheng X, Xie B. Antibacterial Radicicol Analogues from Pochonia chlamydosporia and Their Biosynthetic Gene Cluster. J Agric Food Chem. 2019 Jul 3;67(26):7266-7273. doi: 10.1021/acs.jafc.9b01977. Epub 2019 Jun 24. PMID: 31244199. 3. Shi J, Jiang M, Wang H, Luo Z, Guo Y, Chen Y, Zhao X, Qiang S, Strasser RJ, Kalaji HM, Chen S. Effects of Mycotoxin Fumagillin, Mevastatin, Radicicol, and Wortmannin on Photosynthesis of Chlamydomonas reinhardtii. Plants (Basel). 2023 Feb 2;12(3):665. doi: 10.3390/plants12030665. PMID: 36771749; PMCID: PMC9920790. 4. Oikawa T, Onozawa C, Kuranuki S, Igarashi Y, Sato M, Ashino H, Shimamura M, Toi M, Kurakata S. Dipalmitoylation of radicicol results in improved efficacy against tumor growth and angiogenesis in vivo. Cancer Sci. 2007 Feb;98(2):219-25. doi: 10.1111/j.1349-7006.2006.00359.x. PMID: 17233839.

In vitro protocol:

In vivo protocol:

1. Shi J, Jiang M, Wang H, Luo Z, Guo Y, Chen Y, Zhao X, Qiang S, Strasser RJ, Kalaji HM, Chen S. Effects of Mycotoxin Fumagillin, Mevastatin, Radicicol, and Wortmannin on Photosynthesis of Chlamydomonas reinhardtii. Plants (Basel). 2023 Feb 2;12(3):665. doi: 10.3390/plants12030665. PMID: 36771749; PMCID: PMC9920790. 2. Oikawa T, Onozawa C, Kuranuki S, Igarashi Y, Sato M, Ashino H, Shimamura M, Toi M, Kurakata S. Dipalmitoylation of radicicol results in improved efficacy against tumor growth and angiogenesis in vivo. Cancer Sci. 2007 Feb;98(2):219-25. doi: 10.1111/j.1349-7006.2006.00359.x. PMID: 17233839.

1: Liu Z, Lu Y, Tang D, Zhu J, Luo L, Chen Y, Yu H. Molecular Phylogenetic and Comparative Genomic Analysis of Pleurocordyceps fusiformispora sp. nov. and Perennicordyceps elaphomyceticola in the Family Polycephalomycetaceae. J Fungi (Basel). 2024 Apr 19;10(4):297. doi: 10.3390/jof10040297. PMID: 38667968; PMCID: PMC11050985. 2: da Silva CM, de Lima Neto RG, de Carvalho AMR, Macêdo DPC, de Azevedo Melo AS, Neves RP. Taxonomy of Candida parapsilosis complex isolated from neonates and the role of Hsp90 inhibitors to enhanced the antifungal activity of micafungin. Lett Appl Microbiol. 2024 May 3;77(5):ovae044. doi: 10.1093/lambio/ovae044. PMID: 38658187. 3: Lin HS, Li CH, Chen LW, Wang SS, Chen LY, Hung CH, Lin CL, Chang PJ. The varicella-zoster virus ORF16 protein promotes both the nuclear transport and the protein abundance of the viral DNA polymerase subunit ORF28. Virus Res. 2024 Jul;345:199379. doi: 10.1016/j.virusres.2024.199379. Epub 2024 Apr 26. PMID: 38643859; PMCID: PMC11061344. 4: Yadav M, Sathe J, Teronpi V, Kumar A. Navigating the signaling landscape of Ralstonia solanacearum: a study of bacterial two-component systems. World J Microbiol Biotechnol. 2024 Apr 2;40(5):153. doi: 10.1007/s11274-024-03950-y. PMID: 38564115. 5: Zuccato C, Cosenza LC, Tupini C, Finotti A, Sacchetti G, Simoni D, Gambari R, Lampronti I. New Synthetic Isoxazole Derivatives Acting as Potent Inducers of Fetal Hemoglobin in Erythroid Precursor Cells Isolated from β-Thalassemic Patients. Molecules. 2023 Dec 19;29(1):8. doi: 10.3390/molecules29010008. PMID: 38202591; PMCID: PMC10779815. 6: Martínez-Rodríguez OP, García-Contreras R, Aguayo-Ortiz R, Figueroa M. Antimicrobial and antibiofilm activity of fungal metabolites on methicillin- resistant Staphylococcus aureus (ATCC 43300) mediated by SarA and AgrA. Biofouling. 2023 Aug-Sep;39(8):830-837. doi: 10.1080/08927014.2023.2276926. Epub 2023 Nov 20. PMID: 37929585. 7: Meng Q, Song YL, Zhou C, He H, Zhang N, Zhou H. A hydrogen-deuterium exchange mass spectrometry-based protocol for protein-small molecule interaction analysis. Biophys Rep. 2023 Apr 30;9(2):99-111. doi: 10.52601/bpr.2023.230006. PMID: 37753061; PMCID: PMC10518522. 8: Pokhrel A, Coleman JJ. Inventory of the Secondary Metabolite Biosynthetic Potential of Members within the Terminal Clade of the Fusarium solani Species Complex. J Fungi (Basel). 2023 Jul 28;9(8):799. doi: 10.3390/jof9080799. PMID: 37623570; PMCID: PMC10455376. 9: Wang D, Wang H, Fan L, Ludwig T, Wegner A, Stahl F, Harre J, Warnecke A, Zeilinger C. A Chemical Chaperone Restores Connexin 26 Mutant Activity. ACS Pharmacol Transl Sci. 2023 Jun 1;6(7):997-1005. doi: 10.1021/acsptsci.3c00056. PMID: 37470015; PMCID: PMC10353060. 10: Keller A, Gao LL, Witten D, Dunham MJ. Condition-dependent fitness effects of large synthetic chromosome amplifications. bioRxiv [Preprint]. 2023 Jun 9:2023.06.08.544269. doi: 10.1101/2023.06.08.544269. PMID: 37333112; PMCID: PMC10274924. 11: Singh P, Tabassum W, Fangaria N, Dey S, Padhi S, Bhattacharyya MK, Arun Kumar K, Roy A, Bhattacharyya S. Plasmodium Topoisomerase VIB and Spo11 Constitute Functional Type IIB Topoisomerase in Malaria Parasite: Its Possible Role in Mitochondrial DNA Segregation. Microbiol Spectr. 2023 Jun 15;11(3):e0498022. doi: 10.1128/spectrum.04980-22. Epub 2023 May 22. PMID: 37212694; PMCID: PMC10269783. 12: Liu Y, Li D, Wang S, Peng Z, Tan Q, He Q, Wang J. 6-Gingerol Ameliorates Hepatic Steatosis, Inflammation and Oxidative Stress in High-Fat Diet-Fed Mice through Activating LKB1/AMPK Signaling. Int J Mol Sci. 2023 Mar 27;24(7):6285. doi: 10.3390/ijms24076285. PMID: 37047258; PMCID: PMC10094681. 13: Ausili A. Despite their structural similarities, the cytosolic isoforms of human Hsp90 show different behaviour in thermal unfolding due to their conformation: An FTIR study. Arch Biochem Biophys. 2023 May 15;740:109599. doi: 10.1016/j.abb.2023.109599. Epub 2023 Apr 6. PMID: 37028636. 14: Shi J, Jiang M, Wang H, Luo Z, Guo Y, Chen Y, Zhao X, Qiang S, Strasser RJ, Kalaji HM, Chen S. Effects of Mycotoxin Fumagillin, Mevastatin, Radicicol, and Wortmannin on Photosynthesis of Chlamydomonas reinhardtii. Plants (Basel). 2023 Feb 2;12(3):665. doi: 10.3390/plants12030665. PMID: 36771749; PMCID: PMC9920790. 15: Cadelis MM, Li SA, van de Pas SJ, Grey A, Mulholland D, Weir BS, Copp BR, Wiles S. Antimicrobial Natural Products from Plant Pathogenic Fungi. Molecules. 2023 Jan 23;28(3):1142. doi: 10.3390/molecules28031142. PMID: 36770808; PMCID: PMC9920077. 16: Li G, Xu Y, Li Y, Chang D, Zhang P, Ma Z, Chen D, You Y, Huang X, Cai J. Qiangjing tablets ameliorate asthenozoospermia via mitochondrial ubiquitination and mitophagy mediated by LKB1/AMPK/ULK1 signaling. Pharm Biol. 2023 Dec;61(1):271-280. doi: 10.1080/13880209.2023.2168021. PMID: 36655371; PMCID: PMC9858429. 17: Park JE, Han JS. A bioactive component of Portulaca Oleracea L., HM- chromanone, improves palmitate-induced insulin resistance by inhibiting mTOR/S6K1 through activation of the AMPK pathway in L6 skeletal muscle cells. Toxicol Res (Camb). 2022 Aug 26;11(5):774-783. doi: 10.1093/toxres/tfac055. PMID: 36337245; PMCID: PMC9618117. 18: Ardestani M, Khorsandi Z, Keshavarzipour F, Iravani S, Sadeghi-Aliabadi H, Varma RS. Heterocyclic Compounds as Hsp90 Inhibitors: A Perspective on Anticancer Applications. Pharmaceutics. 2022 Oct 18;14(10):2220. doi: 10.3390/pharmaceutics14102220. PMID: 36297655; PMCID: PMC9610671. 19: de la Cerda Garcia-Caro R, Thompson G, Zhang P, Hokamp K, Roche F, Carlin S, Vrhovsek U, Bond U. Enhanced flavour profiles through radicicol induced genomic variation in the lager yeasts, Saccharomyces pastorianus. Yeast. 2022 Oct;39(10):535-547. doi: 10.1002/yea.3815. Epub 2022 Oct 3. PMID: 36127846. 20: Tabassum W, Bhattacharya M, Bakshi S, Bhattacharyya MK. Heat Shock Protein 90 Regulates the Activity of Histone Deacetylase Sir2 in Plasmodium falciparum. mSphere. 2022 Oct 26;7(5):e0032922. doi: 10.1128/msphere.00329-22. Epub 2022 Sep 19. PMID: 36121150; PMCID: PMC9599603.