Geldanamycin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antineoplastic |
| Catalog number | BBF-01865 |
| CAS | 30562-34-6 |
| Molecular Weight | 560.64 |
| Molecular Formula | C29H40N2O9 |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-01865 | 200 mg | $199 | In stock | |
| BBF-01865 | 500 mg | $419 | In stock |
Online Inquiry
Add to cartDescription
Geldanamycin is a benzoquinone ansamycin antibiotic that inhibits heat shock protein 90 (HSP90). Geldanamycin has been shown to promote survival of neural stem cells from oxidative stress via inhibition of HSP90. It displays potent antineoplastic properties and inhibits myeloma cell growth.
Specification
| Synonyms | geldanomycin; NSC 122750; [(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6-hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate |
| Storage | 3 years -20°C powder, 6 months -80°C in solvent. |
| IUPAC 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 |
| Canonical SMILES | CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)OC)C)OC)OC(=O)N)C)C)O)OC |
| InChI | 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 |
| InChI Key | QTQAWLPCGQOSGP-KSRBKZBZSA-N |
Properties
| Appearance | Solid Powder |
| Application | Antibiotics, Antineoplastic |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; fungi; neoplastics (Tumor); viruses |
| Boiling Point | 627.87°C at 760 mmHg |
| Melting Point | 252-255°C |
| Flash Point | 427.9±32.9 °C |
| Density | 1.2443 g/cm3 |
| Solubility | DMSO ≥ 110mg/mL H2O < 1.2mg/mL Ethanol < 1.2mg/mL |
Reference Reading
1.New C-19-modified geldanamycin derivatives: synthesis, antitumor activities, and physical properties study.
Liu YF1,2, Zhong JJ1, Lin L1, Liu JJ1, Wang YG1, He WQ1, Yang ZY1. J Asian Nat Prod Res. 2016 Mar 18:1-13. [Epub ahead of print]
Thiazinogeldanamycin (2) was identified from Streptomyces hygroscopicus 17997 at the late stage of the fermentation. The pH was firstly proposed as an important factor in the biosynthesis of it. It was verified that 2 was produced by direct chemical reactions between geldanamycin (1, GDM) and cysteine or aminoethanethiol hydrochloride at pH > 7 in vitro. The proposed synthesis pathway for compound 2 was also discussed. Eleven new C-19-modified GDM derivatives, including five stable hydroquinone form derivatives, were synthesized, most of which exhibited desirable properties such as lower cytotoxicity, increased water solubility, and potent antitumor activity. Especially, compounds 5 and 8 showed antitumor activities against HepG2 cell with IC50 values of 2.97-6.61 μM, lower cytotoxicity and at least 15-fold higher water solubility compared with 1 in pH 7.0 phosphate buffer.
2.The non-Geldanamycin Hsp90 inhibitors enhanced the antifungal activity of fluconazole.
Li L1, An M1, Shen H2, Huang X1, Yao X3, Liu J1, Zhu F1, Zhang S1, Chen S1, He L4, Zhang J1, Zou Z3, Jiang Y5. Am J Transl Res. 2015 Dec 15;7(12):2589-602. eCollection 2015.
The molecular chaperone heat shock protein 90 (Hsp90) is highly conserved in eukaryotes and facilitates the correct folding, productive assembly and maturation of a diverse cellular proteins. In fungi, especially the most prevalent human fungal pathogen Candida albicans, Hsp90 influences development and modulates drug resistance. Here, we mainly explore the effect of non-Geldanamycin Hsp90 inhibitor HSP990 on the activity of fluconazole (FLC) against Candida albicans and investigate the underlying mechanism. We demonstrate that HSP990 has potent synergistic antifungal activity with FLC against FLC-resistant C. albicans through the checkerboard microdilution assay,agar diffusion tests and time-kill curves, and shows low cytotoxicity to human umbilical vein endothelial cells. Further study shows that the activity of FLC against C. albicans biofilm formation in vitro is significantly enhanced when used in combination with HSP990. In a murine model of disseminated candidiasis, the therapeutic efficacy of FLC is also enhanced by the pharmacological inhibition of C.
Recommended Products
| BBF-00852 | Epothilon B | Inquiry |
| BBF-03800 | Moxidectin | Inquiry |
| BBF-05725 | Megalomicin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03819 | Spinosyn A | Inquiry |
| BBF-03761 | Tunicamycin | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
