Geldanamycin 格尔德霉素
CAS 30562-34-6 MFCD00274570
化学结构图
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. Formula | C29H40N2O9 |
|---|---|
| Mol. Weight | 561 |
| Density | 1.23 |
| Melting Point | 255°C |
| Appearance | Solid powder |
| Solubility | Soluble in DMSO, not in water |
别名和识别编码
| Chemical Name | Geldanamycin |
|---|---|
| CAS Number | 30562-34-6 |
| 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 Number | MFCD00274570 |
| Reaxys-RN | 6835113 |
| PubChem Substance ID | 87560649 |
| EC Number | 250-023-7 |
| Beilstein Registry Number | 6835113 |
| Chemical Name Translation | 格尔德霉素 |
| Formula | C29H40N2O9 |
| 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 |
| InChIKey | QTQAWLPCGQOSGP-KSRBKZBZSA-N |
| 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 |
| Canonical SMILES | NC(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.
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- 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
- H303 May be harmfully swallowed 吞食可能有害
- P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛，皮肤或衣服。
GHS Symbol
- S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
- 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
