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5mg |
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10mg |
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25mg |
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50mg |
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Purity: ≥98%
Geldanamycin (U-29135; NSC-122750; NSC122750; U 29135) is a natural occurring, benzoquinone-based ,19-membered macrocyle ansamycin class of anticancer antibiotic. It is a crystalline antimicrobial and benzoquinone ansamycin compound extracted from the culture filtrates of Streptomyces hygroscopicus var. geldanus var. nova. Geldanamycin is a specific inhibitor of heat shock protein 90 (HSP90) with potential antineoplastic activity. It inhibits HSP90 with a Kd of 1.2 μM.
ln Vitro |
Viperin induction in RAW264.7 cells is considerably delayed and reduced by geldanamycin, suggesting a role for IRF3 in this process [1]. In cultured primary neurons, the benzoquinone ansamycin geldanamycin protects against neuronal damage caused by oxygen-glucose deprivation (OGD)/zVAD therapy. More significantly, Geldanamycin lowered RIP1 protein levels in a manner that was dependent on both time and concentration. Additionally, geldanamycin lowers Hsp90 protein levels, which causes RIP1 protein instability. As a result, RIP1 protein levels fall following geldanamycin treatment, although RIP1 mRNA levels remain unchanged [2]. The first known Hsp90 inhibitor found in a natural substance is geldanamycin. It inhibits the molecular chaperone function of Hsp90 by binding to its N-terminal ATPase domain, and through the apoptotic mechanism, it greatly causes tumor cell death [3].
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ln Vivo |
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Animal Protocol |
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References |
[1]. Tang HB, et al. Viperin inhibits rabies virus replication via reduced cholesterol and sphingomyelin and is regulated upstream by TLR4. Sci Rep. 2016 Jul 26;6:30529
[2]. Chen WW, et al. RIP1 mediates the protection of Geldanamycin on neuronal injury induced by oxygen-glucosedeprivation combined with zVAD in primary cortical neurons. J Neurochem. 2012 Jan;120(1):70-7. [3]. Lin Z, et al. 17-ABAG, a novel Geldanamycin derivative, inhibits LNCaP-cell proliferation through heat shock protein 90 inhibition. Int J Mol Med. 2015 Aug;36(2):424-32. [4]. Roe SM, et al. Structural basis for inhibition of the Hsp90 molecular chaperone by the antitumor antibiotics radicicol and geldanamycin. J Med Chem. 1999 Jan 28;42(2):260-6. [5]. Wang C, et al. Geldanamycin Reduces Acute Respiratory Distress Syndrome and Promotes the Survival of Mice Infected with the Highly Virulent H5N1 Influenza Virus. Front Cell Infect Microbiol. 2017 Jun 15;7:267. |
Molecular Formula |
C29H40N2O9
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Molecular Weight |
560.64
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CAS # |
30562-34-6
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Related CAS # |
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SMILES |
COC(C(C=C1NC(/C(C)=C/C=C/[C@H](OC)[C@@H](OC(N)=O)/C(C)=C/[C@H](C)[C@H]2O)=O)=O)=C(C[C@H](C[C@@H]2OC)C)C1=O
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InChi Key |
QTQAWLPCGQOSGP-KSRBKZBZSA-N
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InChi Code |
InChI=1S/C29H40N2O9/c1-15-11-19-25(34)20(14-21(32)27(19)39-7)31-28(35)16(2)9-8-10-22(37-5)26(40-29(30)36)18(4)13-17(3)24(33)23(12-15)38-6/h8-10,13-15,17,22-24,26,33H,11-12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8-,16-9+,18-13+/t15-,17+,22+,23+,24-,26+/m1/s1
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Chemical Name |
(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate
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Synonyms |
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
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Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (4.46 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (4.46 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.) |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 1.7837 mL | 8.9184 mL | 17.8368 mL | |
5 mM | 0.3567 mL | 1.7837 mL | 3.5674 mL | |
10 mM | 0.1784 mL | 0.8918 mL | 1.7837 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
NCT00019708 | Terminated | Drug: tanespimycin | Extranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue |
National Cancer Institute (NCI) | June 1999 | Phase 1 |
NCT00003969 | Completed | Drug: tanespimycin | Unspecified Adult Solid Tumor, Protocol Specific |
Cancer Research UK | August 1998 | Phase 1 |
NCT01193491 | Terminated | Drug: IPI-493 | Hematologic Malignancies | Infinity Pharmaceuticals, Inc. | June 2010 | Phase 1 |
NCT00093405 | Completed | Drug: tanespimycin | Kidney Cancer | Memorial Sloan Kettering Cancer Center |
August 2004 | Phase 2 |