Quadrone
(Synonyms: 夸德尔酮) 目录号 : GC41341
A sesquiterpene with anticancer activity
Cas No.:66550-08-1
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Quadrone is a sesquiterpene originally isolated from A. terreus. It is cytotoxic to human carcinoma KB cells in vitro (EC50 = 1.3 μg/ml).
| Cas No. | 66550-08-1 | SDF | |
| 别名 | 夸德尔酮 | ||
| Canonical SMILES | O=C1C[C@@]2([H])[C@@]3([C@@]4([H])CC[C@@]2([H])C(C)(C)C3)[C@@]1([H])COC4=O | ||
| 分子式 | C15H20O3 | 分子量 | 248.3 |
| 溶解度 | Soluble in DMSO | 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 4.0274 mL | 20.1369 mL | 40.2739 mL |
| 5 mM | 0.8055 mL | 4.0274 mL | 8.0548 mL |
| 10 mM | 0.4027 mL | 2.0137 mL | 4.0274 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。
Quadrone, a new antitumor substance produced by Aspergillus terreus. Production, isolation and properties
J Antibiot (Tokyo) 1978 Jan;31(1):38-42.PMID:627521DOI:10.7164/antibiotics.31.38.
A new antitumor compound named Quadrone was isolated from the culture broth of Aspergillus terreus NRRL 11,156. Quadrone was active against KB cells in vitro, but died not possess antimicrobial activity.
[Overview of 40 years' chemical study]
Yakugaku Zasshi 2009 Jan;129(1):107-34.PMID:19122440DOI:10.1248/yakushi.129.107.
1,6-Dihydro-3(2H)-pyridinone, designed as a common synthon for synthesis of various natural products, was found to be easily prepared in large scale and successfully used to synthesize a variety of alkaloids such as ibogamine, quinine and tecomanine. A tricyclo[3.3.0.0(2.8)]octane was also served as a common synthon for several sesquiterpenes such as pentalenene and Quadrone. Synthetic studies by using sulfinyl chirality via an intramolecular Michael addition gave the novel route to construct spiro-ketal moiety in enantiomerically pure form. By applying this method, many natural spiro-ketal compounds were asymmetrically synthesized effectively. 3-Sulfinylated 1,4-dihydropyridine, a chiral NADH model compound, reduced activated ketones such as methyl benzoylformate to give the corresponding alcohols in excellent optical yields. A kind of 3-O-substituted pyridoxal chiral model compound was useful for preparation of alpha,alpha-dialkylated alpha-amino acids by asymmetric alpha-alkylation of alpha-amino acids. 2'-O,4'-C-Bridged nucleic acid analogs, BNAs, developed as novel type of artificial nucleic acids, showed an extraordinarily high binding affinity toward single stranded RNA and double stranded DNA complements along with excellent nuclease-resistant ability. Oligonucleotides containing BNA monomer units were proved to be very useful for various biotechnologies, such as antisense and antigene methodologies.
Determination of the absolute configurations of natural products via density functional theory calculations of optical rotation, electronic circular dichroism, and vibrational circular dichroism: the cytotoxic sesquiterpene natural products Quadrone, suberosenone, suberosanone, and suberosenol A acetate
J Nat Prod 2006 Jul;69(7):1055-64.PMID:16872144DOI:10.1021/np060112p.
The determination of the absolute configurations (ACs) of chiral molecules using the chiroptical techniques of optical rotation (OR), electronic circular dichroism (ECD), and vibrational circular dichroism (VCD) has been revolutionized by the development of density functional theory (DFT) methods for the prediction of these properties. Here, we demonstrate the significance of these advances for the stereochemical characterization of natural products. Time-dependent DFT (TDDFT) calculations of the specific rotations, [alpha](D), of four cytotoxic natural products, Quadrone (1), suberosenone (2), suberosanone (3), and suberosenol A acetate (4), are used to assign their ACs. TDDFT calculations of the ECD of 1 are used to assign its AC. The VCD spectrum of 1 is reported and also used, together with DFT calculations, to assign its AC. The ACs of 1 derived from its [alpha](D), ECD, and VCD are identical and in agreement with the AC previously determined via total synthesis. The previously undetermined ACs of 2-4, derived from their [alpha](D) values, have absolute configurations of their tricyclic cores identical to that of 1. Further studies of the ACs of these molecules using ECD and, especially, VCD are recommended to establish more definitively this finding. Our studies of the OR, ECD, and VCD of Quadrone are the first to utilize DFT calculations of all three properties for the determination of the AC of a chiral natural product molecule.
Microbial hydroxylation of Quadrone to 8a-hydroxyquadrone
J Nat Prod 1987 Jan-Feb;50(1):49-54.PMID:3598598DOI:10.1021/np50049a008.
Microbial transformation of Quadrone and its 4-ethylene ketal with Cunninghamella echinulata afforded the 8a-hydroxyquadrone and its 4-ethylene ketal, respectively.
Alertenone, a dimer of suberosenone from Alertigorgia sp
J Nat Prod 1999 Apr;62(4):633-5.PMID:10217729DOI:10.1021/np980464z.
Bioassay-guided fractionation of organic extracts of the gorgonian Alertigorgia sp. has yielded the previously known suberosenone (1), a cytotoxic tricyclic sesquiterpene of the Quadrone class, and alertenone (2), a dimer of suberosenone. The structure of 2 was determined by spectral analysis; the 1D TOCSY experiment was particularly useful in the structure elucidation. Comparison of the in vitro cytotoxicity of alertenone and suberosenone revealed that the dimeric alertenone was devoid of cytotoxicity below 35 microg/mL. In a hollow-fiber assay model of in vivo activity, suberosenone exhibited some growth inhibition of two of six tumor cell lines tested.