Gedunin | CAS#2753-30-2 | Heat shock protein inhibitor

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

MedKoo CAT#: 112118

CAS#: 2753-30-2

Description: Gedunin is a natural inhibitor of the heat shock protein co-chaperone p23 that also inhibits Hsp90 expression in human teratocarcinomal NTERA-2 cells in vitro.

Chemical Structure

Gedunin

CAS# 2753-30-2

Instruction

Theoretical Analysis

MedKoo Cat#: 112118
Name: Gedunin
CAS#: 2753-30-2
Chemical Formula: C28H34O7
Exact Mass: 482.23
Molecular Weight: 482.570
Elemental Analysis: C, 69.69; H, 7.10; O, 23.21

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 310	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: Gedunin; NSC 113497; NSC113497; NSC-113497

IUPAC/Chemical Name: (1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-1-(furan-3-yl)-4b,7,7,10a,12a-pentamethyl-3,8-dioxo-1,3,3a,4b,5,6,6a,7,8,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]oxireno[2,3-d]isochromen-5-yl acetate

InChi Key: YJXDGWUNRYLINJ-BHAPSIHVSA-N

InChi Code: InChI=1S/C28H34O7/c1-15(29)33-20-13-18-24(2,3)19(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)34-23(31)22-28(26,35-22)27(17,20)6/h8-10,12,14,17-18,20-22H,7,11,13H2,1-6H3/t17-,18+,20-,21+,22-,25-,26+,27+,28-/m1/s1

SMILES Code: O=C1[C@@H]2[C@@]3([C@@]4([C@@H](C[C@]5(C(C)(C(C=C[C@@]5([C@]4(CC[C@]3([C@@H](O1)C6=COC=C6)C)[H])C)=O)C)[H])OC(C)=O)C)O2

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: 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:

Certificate of Analysis:

View CoA: current batch, Lot# C22M07C14

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Acetonitrile	1.0	2.07
	DMSO	48.3	100.00
	Ethanol	1.0	2.07
	Methanol	1.0	2.07

Preparing Stock Solutions

The following data is based on the product molecular weight 482.57 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:

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

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1: Subramani R, Gonzalez E, Nandy SB, Arumugam A, Camacho F, Medel J, Alabi D, Lakshmanaswamy R. Gedunin inhibits pancreatic cancer by altering sonic hedgehog signaling pathway. Oncotarget. 2017 Feb 14;8(7):10891-10904. doi: 10.18632/oncotarget.8055. PMID: 26988754; PMCID: PMC5355232.

2: Tom S, Rane A, Katewa AS, Chamoli M, Matsumoto RR, Andersen JK, Chinta SJ. Gedunin Inhibits Oligomeric Aβ1-42-Induced Microglia Activation Via Modulation of Nrf2-NF-κB Signaling. Mol Neurobiol. 2019 Nov;56(11):7851-7862. doi: 10.1007/s12035-019-1636-9. Epub 2019 May 24. PMID: 31127528.

3: Conte FP, Ferraris FK, Costa TE, Pacheco P, Seito LN, Verri WA Jr, Cunha FQ, Penido C, Henriques MG. Effect of gedunin on acute articular inflammation and hypernociception in mice. Molecules. 2015 Feb 3;20(2):2636-57. doi: 10.3390/molecules20022636. PMID: 25654532; PMCID: PMC6272452.

4: Ferraris FK, Moret KH, Figueiredo AB, Penido C, Henriques Md. Gedunin, a natural tetranortriterpenoid, modulates T lymphocyte responses and ameliorates allergic inflammation. Int Immunopharmacol. 2012 Sep;14(1):82-93. doi: 10.1016/j.intimp.2012.06.002. Epub 2012 Jun 15. PMID: 22709475.

5: Hasan A, Haque E, Hameed R, Maier PN, Irfan S, Kamil M, Nazir A, Mir SS. Hsp90 inhibitor gedunin causes apoptosis in A549 lung cancer cells by disrupting Hsp90:Beclin-1:Bcl-2 interaction and downregulating autophagy. Life Sci. 2020 Sep 1;256:118000. doi: 10.1016/j.lfs.2020.118000. Epub 2020 Jun 22. PMID: 32585246.

6: Tharmarajah L, Samarakoon SR, Ediriweera MK, Piyathilaka P, Tennekoon KH, Senathilake KS, Rajagopalan U, Galhena PB, Thabrew I. In Vitro Anticancer Effect of Gedunin on Human Teratocarcinomal (NTERA-2) Cancer Stem-Like Cells. Biomed Res Int. 2017;2017:2413197. doi: 10.1155/2017/2413197. Epub 2017 Jun 7. PMID: 28680880; PMCID: PMC5478822.

7: Kamath SG, Chen N, Xiong Y, Wenham R, Apte S, Humphrey M, Cragun J, Lancaster JM. Gedunin, a novel natural substance, inhibits ovarian cancer cell proliferation. Int J Gynecol Cancer. 2009 Dec;19(9):1564-9. doi: 10.1111/IGC.0b013e3181a83135. PMID: 19955938.

8: Tanagala KKK, Baba AB, Kowshik J, Reddy GB, Nagini S. Gedunin, A Neem Limonoid in Combination with Epalrestat Inhibits Cancer Hallmarks by Attenuating Aldose Reductase-Driven Oncogenic Signaling in SCC131 Oral Cancer Cells. Anticancer Agents Med Chem. 2018;18(14):2042-2052. doi: 10.2174/1871520618666180731093433. PMID: 30062975.

9: Sahai R, Bhattacharjee A, Shukla VN, Yadav P, Hasanain M, Sarkar J, Narender T, Mitra K. Gedunin isolated from the mangrove plant Xylocarpus granatum exerts its anti-proliferative activity in ovarian cancer cells through G2/M-phase arrest and oxidative stress-mediated intrinsic apoptosis. Apoptosis. 2020 Aug;25(7-8):481-499. doi: 10.1007/s10495-020-01605-5. PMID: 32399945.

10: Patwardhan CA, Fauq A, Peterson LB, Miller C, Blagg BS, Chadli A. Gedunin inactivates the co-chaperone p23 protein causing cancer cell death by apoptosis. J Biol Chem. 2013 Mar 8;288(10):7313-25. doi: 10.1074/jbc.M112.427328. Epub 2013 Jan 25. PMID: 23355466; PMCID: PMC3591639.

11: Kishore T KK, Ganugula R, Gade DR, Reddy GB, Nagini S. Gedunin abrogates aldose reductase, PI3K/Akt/mToR, and NF-κB signaling pathways to inhibit angiogenesis in a hamster model of oral carcinogenesis. Tumour Biol. 2016 Feb;37(2):2083-93. doi: 10.1007/s13277-015-4003-0. Epub 2015 Sep 5. PMID: 26342697.

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