Geldanamycin

Quality 0.50 · 2 views · Updated 2 months ago

title: "Geldanamycin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["1,4-benzoquinones", "carbamates", "lactams", "phenol-ethers", "ethers", "secondary-alcohols", "ansamycins"] topic_path: "general/1-4-benzoquinones" source: "https://en.wikipedia.org/wiki/Geldanamycin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 443833298 | ImageFile = Geldanamycin.svg | ImageSize = | IUPACName = (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 | OtherNames = |Section1={{Chembox Identifiers | Abbreviations = | ChemSpiderID_Ref = | ChemSpiderID = 10272739 | ChEMBL_Ref = | ChEMBL = 278315 | 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 | InChIKey = QTQAWLPCGQOSGP-KSRBKZBZBP | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = QTQAWLPCGQOSGP-KSRBKZBZSA-N | InChIKey1 = QTQAWLPCGQOSGP-KSRBKZBZSA-N | CASNo_Ref = | CASNo = 30562-34-6 | UNII_Ref = | UNII = Z3K3VJ16KU | EINECS = | PubChem = 5288382 | DrugBank_Ref = | DrugBank = DB02424 | SMILES = NC(=O)O[C@H]1C(/C)=C/C@HC@@HC@@HCC@HC\C2=C(/OC)C(=O)\C=C(\NC(=O)C(\C)=C\C=C/[C@@H]1OC)C2=O | RTECS = | MeSHName = | ChEBI_Ref = | ChEBI = 5292 | KEGG_Ref = | KEGG = |Section2={{Chembox Properties | Formula = C29H40N2O9 | MolarMass = 560.64 g/mol | Appearance = Gold-yellow fine crystalline powder | Density = | MeltingPt = | MeltingPt_notes = | BoilingPt = | BoilingPt_notes = | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = | IsoelectricPt = | SpecRotation = | RefractIndex = | Viscosity = | Dipole = |Section3={{Chembox Structure | CrystalStruct = | Coordination = | MolShape = | Dipole = |Section4={{Chembox Thermochemistry | DeltaHf = | DeltaHc = | Entropy = | HeatCapacity = |Section5={{Chembox Pharmacology | AdminRoutes = | Bioavail = | Metabolism = | HalfLife = | ProteinBound = | Excretion = | Legal_status = | Legal_US = | Legal_UK = | Legal_AU = | Legal_CA = | Pregnancy_category = | Pregnancy_AU = | Pregnancy_US = |Section6={{Chembox Explosive | ShockSens = | FrictionSens = | DetonationV = | REFactor = |Section7={{Chembox Hazards | ExternalSDS = | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = |Section8={{Chembox Related | OtherAnions = | OtherCations = | OtherFunction = | OtherFunction_label = | OtherCompounds = Geldanamycin is a 1,4-benzoquinone ansamycin antitumor antibiotic that inhibits the function of Hsp90 (Heat Shock Protein 90) by binding to the unusual ADP/ATP-binding pocket of the protein.{{Cite journal | last1 = Schulte | first1 = T. W. | last2 = Akinaga | first2 = S. | last3 = Soga | first3 = S. | last4 = Sullivan | first4 = W. | last5 = Stensgard | first5 = B. | last6 = Toft | first6 = D. | last7 = Neckers | first7 = L. M. | title = Antibiotic radicicol binds to the N-terminal domain of Hsp90 and shares important biologic activities with geldanamycin | journal = Cell Stress & Chaperones | volume = 3 | issue = 2 | pages = 100–108 | year = 1998 | doi = 10.1379/1466-1268(1998)0032.3.CO;2 | doi-broken-date = 12 July 2025 | pmid = 9672245 | pmc = 312953

::figure[src="https://upload.wikimedia.org/wikipedia/commons/f/f0/1yetgdm.png" caption="1yet}}{{Cite journal"] ::

| last1 = Stebbins | first1 = C. E. | last2 = Russo | first2 = A. A. | last3 = Schneider | first3 = C. | last4 = Rosen | first4 = N. | last5 = Hartl | first5 = F. U. | last6 = Pavletich | first6 = N. P. | title = Crystal structure of an Hsp90-geldanamycin complex: Targeting of a protein chaperone by an antitumor agent | journal = Cell | volume = 89 | issue = 2 | pages = 239–250 | year = 1997 | pmid = 9108479 | doi=10.1016/S0092-8674(00)80203-2 | s2cid = 5253110 | doi-access = free

Biosynthesis

Geldanamycin was originally discovered in the organism Streptomyces hygroscopicus.{{Cite journal | last1 = He | first1 = W. | last2 = Wu | first2 = L. | last3 = Gao | first3 = Q. | last4 = Du | first4 = Y. | last5 = Wang | first5 = Y. | title = Identification of AHBA Biosynthetic Genes Related to Geldanamycin Biosynthesis in Streptomyces hygroscopicus 17997 | doi = 10.1007/s00284-005-0203-y | journal = Current Microbiology | volume = 52 | issue = 3 | pages = 197–203 | year = 2006 | pmid = 16502293 | s2cid = 22291736 | last1 = Kim | first1 = W. | last2 = Lee | first2 = D. | last3 = Hong | first3 = S. S. | last4 = Na | first4 = Z. | last5 = Shin | first5 = J. C. | last6 = Roh | first6 = S. H. | last7 = Wu | first7 = C. Z. | last8 = Choi | first8 = O. | last9 = Lee | first9 = K. | last10 = Shen | first10 = Y. M. | last11 = Paik | first11 = S. G. | last12 = Lee | first12 = J. J. | last13 = Hong | first13 = Y. S. | title = Rational Biosynthetic Engineering for Optimization of Geldanamycin Analogues | doi = 10.1002/cbic.200800763 | journal = ChemBioChem | volume = 10 | issue = 7 | pages = 1243–1251 | year = 2009 | pmid = 19308924 | s2cid = 3273370 | last1 = Lee | first1 = D. | last2 = Lee | first2 = K. | last3 = Cai | first3 = X. F. | last4 = Dat | first4 = N. T. | last5 = Boovanahalli | first5 = S. K. | last6 = Lee | first6 = M. | last7 = Shin | first7 = J. C. | last8 = Kim | first8 = W. | last9 = Jeong | first9 = J. K. | last10 = Lee | first10 = J. S. | last11 = Lee | first11 = C. H. | last12 = Lee | first12 = J. H. | last13 = Hong | first13 = Y. S. | last14 = Lee | first14 = J. J. | title = Biosynthesis of the Heat-Shock Protein 90 Inhibitor Geldanamycin: New Insight into the Formation of the Benzoquinone Moiety | doi = 10.1002/cbic.200500441 | journal = ChemBioChem | volume = 7 | issue = 2 | pages = 246–248 | year = 2006 | pmid = 16381049 | s2cid = 42998903

Notes

References

  • {{Cite journal | last1 = Bedin | first1 = M. | last2 = Gaben | first2 = A. M. | last3 = Saucier | first3 = C. C. | last4 = Mester | first4 = J. | title = Geldanamycin, an inhibitor of the chaperone activity of HSP90, induces MAPK-independent cell cycle arrest | doi = 10.1002/ijc.20010 | journal = International Journal of Cancer | volume = 109 | issue = 5 | pages = 643–652 | year = 2004 | pmid = 14999769 | s2cid = 39451213 | doi-access = free

References

  1. (2011). "Molecular Chaperones".
  2. (2013). "Geldanamycin-Induced Phosphatidylserine Translocation in the Erythrocyte Membrane". Cell Physiol Biochem.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

1,4-benzoquinonescarbamateslactamsphenol-ethersetherssecondary-alcoholsansamycins