Geldanamycin 格尔德霉素

CAS 30562-34-6 MFCD00274570

化学结构图

30562-34-6
SMILES: COC1=C2C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@H](OC(N)=O)[C@@H](OC)/C=C\C=C(/C)C(=O)NC(=CC1=O)C2=O

化学属性

Mol. FormulaC29H40N2O9
Mol. Weight561
Density1.23
Melting Point255°C
Appearance Solid powder
SolubilitySoluble in DMSO, not in water

别名和识别编码

Chemical NameGeldanamycin
CAS Number30562-34-6
Synonym (+)-Geldanamycin 9,13-Dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione 9-Carbamate Geldanamycin from Streptomyces hygroscopicus NSC 122750 NSC 122750; NSC-122750; NSC122750; U 29135; U-29135; U29135. Geldanamycin. NSC 212518 U-29135
MDL NumberMFCD00274570
Reaxys-RN6835113
PubChem Substance ID87560649
EC Number250-023-7
Beilstein Registry Number6835113
Chemical Name Translation格尔德霉素
FormulaC29H40N2O9
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
InChIKeyQTQAWLPCGQOSGP-KSRBKZBZSA-N
InChIInChI=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
Canonical SMILESNC(O[C@@H](/C(C)=C/[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC1=C2OC)[C@@H](OC)/C=C\C=C(C)\C(NC(C1=O)=CC2=O)=O)=O
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分类

  • Heterocycles
  • {SNA} Antibiotics, Antibiotics A to Z, Antibiotics G-M, Antibiotics by Application, Antineoplastic and Immunosuppressive Antibiotics, Antitumor Agents, Benzenoids, Bioactive Small Molecules, Biochemicals and Reagents, Cancer Research, Cell Biology, Cell Signaling and Neuroscience, Chemical Structure Class, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Enzymes, Inhibitors, and Substrates, G, HSP-90 Inhibitors, Inhibits an Enzyme, Kinase/Phosphatase Biology, Mechanism of Action, Molecular Biology, P to Q, Phosphorylation Analysis,

产品应用

  • Geldanamycin is a benzoquinone ansamycin antibiotic that binds to Hsp90 (Heat Shock Protein 90) and inhibits its function. HSP90 client proteins play important roles in the regulation of the cell cycle, cell growth, cell survival, apoptosis, angiogenesis and oncogenesis. Hsp90-geldanamycin complex. PDB 1yet Geldanamycin induces the degradation of proteins that are mutated in tumor cells such as v-Src, Bcr-Abl and p53 preferentially over their normal cellular counterparts. This effect is mediated via HSP90. Despite its potent antitumor potential, geldanamycin presents several major drawbacks as a drug candidate (namely, hepatotoxicity) that have led to the development of geldanamycin analogues.

相关文献及参考

  • [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.
  • ########
  • Chavany, C., et al., p185erbB2 binds to GRP94 in vivo. Dissociation of the p185erbB2/GRP94 heterocomplex by benzoquinone ansamycins precedes depletion of p185erbB2.

安全信息

RTECSLX8920000
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
WGK Germany2
Storage condition <0°C <;0 Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). 储存温度:-20℃
Signal word Warning
Hazard statements
  • H303 May be harmfully swallowed 吞食可能有害
Precautionary statements
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛，皮肤或衣服。
GHS Symbol
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
TYPE OF TEST            : LD - Lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Mammal - dog
DOSE/DURATION           : >4200 ug/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   CCPHDZ Cancer Chemotherapy and Pharmacology.  (Springer-Verlag New York,
   Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094)  V.1-    1978-
   Volume(issue)/page/year: 36,305,1995

TYPE OF TEST            : LD - Lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >50 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   CCPHDZ Cancer Chemotherapy and Pharmacology.  (Springer-Verlag New York,
   Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094)  V.1-    1978-
   Volume(issue)/page/year: 36,305,1995

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 2500 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JANTAJ Journal of Antibiotics.  (Japan Antibiotics Research Assoc., 2-20-8
   Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan)  V.2-5, 1948-52;  V.21- 1968-
   Volume(issue)/page/year: 23,442,1970

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   UPJOH* "Compounds Available for Fundamental Research, Volume II-6,
   Antibiotics, A Program of Upjohn Company Research Laboratory."  (Kalamazoo,
   MI 49001)  Volume(issue)/page/year: 2(6),-,1971

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 1 mg/L
REFERENCE :
   JANTAJ Journal of Antibiotics.  (Japan Antibiotics Research Assoc., 2-20-8
   Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan)  V.2-5, 1948-52;  V.21- 1968-
   Volume(issue)/page/year: 35,886,1982

系列性分类

  1. Life Science 生命科学
  2. Antibiotics 抗生素
  3. Antibiotics A to Z - Antibiotics
  4. Antibiotics G-M - Antibiotics A to Z
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Enzymes, Inhibitors, and Substrates - Biochemicals and Reagents
  4. Enzyme Inhibitors - Enzymes, Inhibitors, and Substrates
  5. Enzyme Inhibitors by Enzyme - Enzyme Inhibitors
  6. P to Q - Enzyme Inhibitors by Enzyme
  7. Protein kinase erbB2,2 - P to Q
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Kinase/Phosphatase Biology - Cell Signaling and Neuroscience
  5. Receptor Tyrosine Kinase Biology - Kinase/Phosphatase Biology
  6. Receptor Tyrosine Kinase Inhibitors - Receptor Tyrosine Kinase Biology
  7. Tyrosine Kinase (TK) - Receptor Tyrosine Kinase Inhibitors
  1. Medical Research Areas
  2. Angiogenesis
  3. Bcr-Abl
  1. Medical Research Areas
  2. Angiogenesis
  3. Src
  1. Medical Research Areas
  2. Cytosketetal Signaling
  3. Bcr-Abl
  1. Medical Research Areas
  2. Metabolism
  3. HSP  (热休克蛋白)

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