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

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

MedKoo CAT#: 562206

CAS#: 12772-57-5

Description: Radicicol is an Hsp90 N-terminal inhibitor.

Chemical Structure

Radicicol

CAS# 12772-57-5

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 562206
Name: Radicicol
CAS#: 12772-57-5
Chemical Formula: C18H17ClO6
Exact Mass: 364.07
Molecular Weight: 364.780
Elemental Analysis: C, 59.27; H, 4.70; Cl, 9.72; O, 26.32

Price and Availability

Size	Price	Availability
1mg	USD 220	2 Weeks
5mg	USD 600	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: 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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Ethanol	3.7	10.00

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:	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.
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.

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1: Dlugosz A, Janecka A. Novobiocin Analogs as Potential Anticancer Agents. Mini Rev Med Chem. 2017;17(9):728-733. doi: 10.2174/1389557516666161223155525. Review. PubMed PMID: 28019639.

2: Michela P, Velia V, Aldo P, Ada P. Role of connexin 43 in cardiovascular diseases. Eur J Pharmacol. 2015 Dec 5;768:71-6. doi: 10.1016/j.ejphar.2015.10.030. Epub 2015 Oct 20. Review. PubMed PMID: 26499977.

3: Trendowski M. PU-H71: An improvement on nature's solutions to oncogenic Hsp90 addiction. Pharmacol Res. 2015 Sep;99:202-16. doi: 10.1016/j.phrs.2015.06.007. Epub 2015 Jun 25. Review. PubMed PMID: 26117427.

4: Khandelwal A, Crowley VM, Blagg BSJ. Natural Product Inspired N-Terminal Hsp90 Inhibitors: From Bench to Bedside? Med Res Rev. 2016 Jan;36(1):92-118. doi: 10.1002/med.21351. Epub 2015 May 25. Review. PubMed PMID: 26010985; PubMed Central PMCID: PMC4659773.

5: Patocka J, Soukup O, Kuca K. Resorcylic acid lactones as the protein kinase inhibitors , naturally occuring toxins. Mini Rev Med Chem. 2013 Nov;13(13):1873-8. Review. PubMed PMID: 24070207.

6: Piper PW, Millson SH. Spotlight on the microbes that produce heat shock protein 90-targeting antibiotics. Open Biol. 2012 Dec 12;2(12):120138. doi: 10.1098/rsob.120138. Review. PubMed PMID: 23271830; PubMed Central PMCID: PMC3603443.

7: Soga S, Akinaga S, Shiotsu Y. Hsp90 inhibitors as anti-cancer agents, from basic discoveries to clinical development. Curr Pharm Des. 2013;19(3):366-76. Review. PubMed PMID: 22920907.

8: Gorska M, Popowska U, Sielicka-Dudzin A, Kuban-Jankowska A, Sawczuk W, Knap N, Cicero G, Wozniak F. Geldanamycin and its derivatives as Hsp90 inhibitors. Front Biosci (Landmark Ed). 2012 Jun 1;17:2269-77. Review. PubMed PMID: 22652777.

9: Neckers L, Workman P. Hsp90 molecular chaperone inhibitors: are we there yet? Clin Cancer Res. 2012 Jan 1;18(1):64-76. doi: 10.1158/1078-0432.CCR-11-1000. Review. PubMed PMID: 22215907; PubMed Central PMCID: PMC3252205.

10: Luo HM, Sun W, Yin JY, Yang XH. [Progress in the study of heat shock protein 90 inhibitors]. Yao Xue Xue Bao. 2010 Jul;45(7):813-20. Review. Chinese. PubMed PMID: 20931776.

11: Minuth WW, Denk L, Glashauser A. Cell and drug delivery therapeutics for controlled renal parenchyma regeneration. Adv Drug Deliv Rev. 2010 Jun 15;62(7-8):841-54. doi: 10.1016/j.addr.2010.01.004. Epub 2010 Feb 1. Review. PubMed PMID: 20122975.

12: Winssinger N, Fontaine JG, Barluenga S. Hsp90 inhibition with resorcyclic acid lactones (RALs). Curr Top Med Chem. 2009;9(15):1419-35. Review. PubMed PMID: 19860733.

13: Reikvam H, Ersvaer E, Bruserud O. Heat shock protein 90 - a potential target in the treatment of human acute myelogenous leukemia. Curr Cancer Drug Targets. 2009 Sep;9(6):761-76. Review. PubMed PMID: 19754360.

14: Sgobba M, Rastelli G. Structure-based and in silico design of Hsp90 inhibitors. ChemMedChem. 2009 Sep;4(9):1399-409. doi: 10.1002/cmdc.200900256. Review. PubMed PMID: 19685544.

15: Duerfeldt AS, Blagg BS. Hydrating for resistance to radicicol. ACS Chem Biol. 2009 Apr 17;4(4):245-7. doi: 10.1021/cb9000712. Review. PubMed PMID: 19371133; PubMed Central PMCID: PMC2843399.

16: Taldone T, Sun W, Chiosis G. Discovery and development of heat shock protein 90 inhibitors. Bioorg Med Chem. 2009 Mar 15;17(6):2225-35. doi: 10.1016/j.bmc.2008.10.087. Epub 2008 Nov 6. Review. PubMed PMID: 19017562; PubMed Central PMCID: PMC2760286.

17: Donnelly A, Blagg BS. Novobiocin and additional inhibitors of the Hsp90 C-terminal nucleotide-binding pocket. Curr Med Chem. 2008;15(26):2702-17. Review. PubMed PMID: 18991631; PubMed Central PMCID: PMC2729083.

18: Workman P, Burrows F, Neckers L, Rosen N. Drugging the cancer chaperone HSP90: combinatorial therapeutic exploitation of oncogene addiction and tumor stress. Ann N Y Acad Sci. 2007 Oct;1113:202-16. Epub 2007 May 18. Review. PubMed PMID: 17513464.

19: Winssinger N, Barluenga S. Chemistry and biology of resorcylic acid lactones. Chem Commun (Camb). 2007 Jan 7;(1):22-36. Epub 2006 Sep 25. Review. PubMed PMID: 17279252.

20: Xiao L, Lu X, Ruden DM. Effectiveness of hsp90 inhibitors as anti-cancer drugs. Mini Rev Med Chem. 2006 Oct;6(10):1137-43. Review. PubMed PMID: 17073714.

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