Gilvocarcin M
(Synonyms: 古铜色菌素M) 目录号 : GC43755
An antibiotic
Cas No.:77879-89-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Gilvocarcin M is an antibiotic originally isolated from S. gilvotanareus. It is active against S. aureus when used at a concentration of 32 µg/ml. Gilvocarcin M inhibits growth of KB cells (IC50 = 0.52 µg/ml) but has no effect on survival in a P388 mouse model of leukemia when used at doses ranging from 25 to 400 mg/kg. Gilvocarcin M intercalates into bacteriophage PM2 DNA. It is toxic to rats with an intravenous LD50 value of 450 mg/kg.
| Cas No. | 77879-89-1 | SDF | |
| 别名 | 古铜色菌素M | ||
| Canonical SMILES | O=C(O1)C2=C(C(OC)=CC(C)=C2)C3=C1C4=C([C@H]5O[C@@]([H])([C@H](O)C)[C@H](O)[C@H]5O)C=CC(O)=C4C(OC)=C3 | ||
| 分子式 | C26H26O9 | 分子量 | 482.5 |
| 溶解度 | DMF: soluble,DMSO: soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.0725 mL | 10.3627 mL | 20.7254 mL |
| 5 mM | 0.4145 mL | 2.0725 mL | 4.1451 mL |
| 10 mM | 0.2073 mL | 1.0363 mL | 2.0725 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Inactivation of the ketoreductase gilU gene of the gilvocarcin biosynthetic gene cluster yields new analogues with partly improved biological activity
Chembiochem 2009 Jan 26;10(2):278-86.PMID:19067453DOI:10.1002/cbic.200800348.
Four new analogues of the gilvocarcin-type aryl-C-glycoside antitumor compounds, namely 4'-hydroxy gilvocarcin V (4'-OH-GV), 4'-hydroxy Gilvocarcin M, 4'-hydroxy gilvocarcin E and 12-demethyl-defucogilvocarcin V, were produced through inactivation of the gilU gene. The 4'-OH-analogues showed improved activity against lung cancer cell lines as compared to their parent compounds without 4'-OH group (gilvocarcins V and E). The structures of the sugar-containing new mutant products indicate that the enzyme GilU acts as an unusual ketoreductase involved in the biosynthesis of the C-glycosidically linked deoxysugar moiety of the gilvocarcins. The structures of the new gilvocarcins indicate substrate flexibility of the post-polyketide synthase modifying enzymes, particularly the C-glycosyltransferase and the enzyme responsible for the sugar ring contraction. The results also shed light into biosynthetic sequence of events in the late steps of biosynthetic pathway of gilvocarcin V.
Photophysical properties of gilvocarcins V and M and their binding constant to calf thymus DNA
Photochem Photobiol 1997 May;65(5):802-10.PMID:9155255DOI:10.1111/j.1751-1097.1997.tb01927.x.
Absorption and emission techniques were used to characterize the ground (S0), singlet (S1) and triplet states (T1) of gilvocarcin V (GV) and Gilvocarcin M (GM) in different solvents. Aggregation of GV with dimerization constant equal to 7800 M-1 is observed in 10% dimethyl-sulfoxide (DMSO)/water. The photophysical properties of the S1 state of these molecules are more sensitive to changes in solvent characteristics than the corresponding ground states. The absorption of visible light by GV and GM results in a higher dipole moment of the excited state causing a red shift in the fluorescence spectra with increasing solvent polarity. The fluorescence quantum yield remains practically unchanged with changes in solvent properties unless water is present as a co-solvent. Both phi f and tau f values corresponding to GV in DMSO are larger than those of GM, whereas in 10% DMSO/H2O the opposite is observed. Thus, GV is more susceptible to other deactivation pathways besides emission in the presence of water than GM. The relative phosphorescence quantum yield (phi p = 0.03) and the triplet energy (ET = 52 kcal/mol) of GV and GM are similar. The S0-S1 energy difference is 63 kcal/mol for GV, whereas for GM it is 67. Thus, the singlet-triplet energy difference is 11 and 15 kcal/mol, respectively. The PM3/CI calculated electronic structures of these compounds are consistent with the observed photophysical properties. The dark binding constants of GV to calf thymus DNA ([1.1-0.08] x 10(6) M-1) are about an order of magnitude larger than those of GM ([0.24-0.018] x 10(6) M-1) at different ionic strengths (0-2.00 M NaCl). Also, the number of gilvocarcin molecules bound per base pair is smaller for GM than for GV. These differences in dark DNA binding parameters between GV and GM could have implications in the large photocytotoxic ability of GV as compared to GM.
Model studies towards the synthesis of Gilvocarcin M
Org Biomol Chem 2005 Dec 21;3(24):4432-43.PMID:16327904DOI:10.1039/b512851j.
In model studies towards the synthesis of Gilvocarcin M, a convergent, xanthate-based free-radical strategy was tested in order to construct the key aromatic ring attached to the sugar unit.
The photobiological differences of gilvocarcins V and M are not related to their transient intermediates and triplet yields
Photochem Photobiol 1998 Jul;68(1):25-31.PMID:9679448doi
The transient absorption spectra of the intermediates produced by the 355 nm laser excitation of gilvocarcin derivatives have been investigated in various solvents. The spectra consist of a triplet-triplet absorption in the visible region and a residual absorption observed between 340 and 700 nm due to a long-lived species, assigned to the radical cation. A broad-fast decaying band with a maximum at around 700 nm attributed to the solvated electron is also seen in solutions containing a low DMSO/water volume ratio and at 266 nm irradiation of a 50% methanol/water solvent mixture. The molar absorption coefficient of the triplet state of gilvocarcin V (GV) and Gilvocarcin M (GM), determined by the energy transfer method, is independent of the solvent properties and has a value of 3.0 x 10(4)/Mcm. The triplet decay rate constants for both drugs are between 1 and 5 x 10(4)/s. A similar initial yield and triplet decay rate constant of GV were observed in the presence of 3.4 mM thymine. Thus, a quenching rate constant of the GV's triplet state by thymine is estimated to be lower than 10(6)/Ms. The triplet quantum yields of both antibiotics determined by using the comparative method are higher in dimethylsulfoxide (DMSO) (0.18) than are those corresponding to 25% DMSO/water (0.06). The decrease in phi T in the presence of water could be attributed to an enhanced internal conversion rate constant from the S1 state or to an increase in the photoionization yield. The similarity of the transient intermediates and their yields for GV and GM suggest that their photobiological differences are due to other factors such as DNA binding constants, preferential localization of the drugs in the cell or the enhanced reactivity of the vinyl group toward cellular components.
Gilvocarcins, new antitumor antibiotics. 2. Structural elucidation
J Antibiot (Tokyo) 1981 Mar;34(3):271-5.PMID:7275808DOI:10.7164/antibiotics.34.271.
Gilvocarcin V(1), C27H28O9, m.p. 264 approximately 267 degrees C (dec.), and Gilvocarcin M(2), C26H26O9, m.p. 245 approximately 248 degrees C (dec.), are new antitumor antibiotics produced by Streptomyces gilvotanareus. The structure of gilvocarcins has been determined by chemical degradation, nmr and mass spectra. They have a benzonaphtopyran-one system, to which the furanose moiety is linked through a C-C glycosyl bond.