16-Dehydroprogesterone
(Synonyms: 16-去氢黄体酮) 目录号 : GC35058
16-Dehydroprogesterone is a chemical derived from a progesterone.
Cas No.:1096-38-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
16-Dehydroprogesterone is a chemical derived from a progesterone.
| Cas No. | 1096-38-4 | SDF | |
| 别名 | 16-去氢黄体酮 | ||
| Canonical SMILES | CC(C1=CC[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O)=O | ||
| 分子式 | C21H28O2 | 分子量 | 312.45 |
| 溶解度 | DMSO: 25 mg/mL (80.01 mM) | 储存条件 | 4°C, protect from light |
| 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 | 3.2005 mL | 16.0026 mL | 32.0051 mL |
| 5 mM | 0.6401 mL | 3.2005 mL | 6.401 mL |
| 10 mM | 0.3201 mL | 1.6003 mL | 3.2005 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。
Synthesis and evaluation of the antiproliferative activity of benzylidenes of 16-Dehydroprogesterone series
Steroids 2018 Oct;138:91-101.PMID:29997047DOI:10.1016/j.steroids.2018.06.013.
Novel benzylidenes (chalcones) of the 16-Dehydroprogesterone series have been characterized and their antitumor activity against two breast cancer cell lines was evaluated. Benzylidenes exhibit significant antiproliferative effect on cells and inhibit cell growth in hormone-dependent MCF-7 and hormone-independent MDA-MB-231 breast cancer cell lines. Compound 3d exhibits the highest activity against two breast cancer cell lines, with the IC50 value of about 2 µM. Compounds 3e,m,n display considerable selectivity for hormone-dependent breast cancer cells, with the IC50 value lower than 6 µM. Moreover, these steroidal benzylidenes regulate ERα signaling and reveal p53-independent mechanism of pro-apoptotic action in MCF-7 cells. The new class of antitumor compounds holds promise as the basis for the design of agents for cancer therapy.
Characteristics of 16-Dehydroprogesterone reductase in cell extracts of the intestinal anaerobe, Eubacterium sp. strain 144
J Steroid Biochem Mol Biol 1991 Feb;38(2):257-63.PMID:2004047DOI:10.1016/0960-0760(91)90134-q.
16-Dehydroprogesterone reductase (16-DHPR) activity was present in cell extracts of Eubacterium sp. strain 144 only when the organism was grown in the presence of steroids containing a delta 16-17 double bond and C-20-ketone. Cells grown with 16-dehydropregnenolone contained 16-DHPR activity but lacked delta 4-5-3-keto steroid reductase activity. Pyruvate or sodium dithionite served as electron donors for 16-DHPR and both reactions required methyl viologen as an electron carrier. Neither NADH nor NADPH, with or without flavin nucleotides, were used by 16-DHPR. Enzyme activity was detected in the cytoplasmic fraction (40%) and membrane fraction (20%) of crude cell extracts, but 40% of the activity was unaccounted for following ultracentrifugation. 16-DHPR activity was unaffected by pH in potassium phosphate buffer over the range 5.0 to 8.5, but was inhibited by Tris-HCl above pH 7.0. 16-DHPR activity was inhibited by sulfhydryl reagents, but inhibitors of electron transport reactions or metal chelators did not affect the enzyme.
Biotransformation of 16-Dehydroprogesterone by the intestinal anaerobic bacterium, Eubacterium sp. 144
J Steroid Biochem 1984 Jul;21(1):65-72.PMID:6748657DOI:10.1016/0022-4731(84)90061-x.
Eubacterium sp. 144 biotransformed 16-Dehydroprogesterone by initially hydrating approx 50% to 16 alpha-hydroxyprogesterone. The detection of this reaction was dependent, in part, on the solubility state of 16-Dehydroprogesterone and was less extensive when the concentration of methanol was insufficient to solubilize the steroid. Cultures containing a mixture of 16-Dehydroprogesterone and 16 alpha-hydroxyprogesterone formed isoprogesterone as a final steroid end product. However, the extent of the reductive reaction was influenced by culture age at the time of 16-Dehydroprogesterone addition and decreased in older cultures. Moreover, both mid- and late-log phase cells also formed progesterone as a reduced steroid end product. The enzyme(s) responsible for isoprogesterone formation (16-Dehydroprogesterone reductase) appeared to be inducible because activity was not evident until 3-6 h after the addition of 16-Dehydroprogesterone to early log-phase cultures. Growth inhibitory concentrations of chloramphenicol or rifampin prevented isoprogesterone formation, but not the production of progesterone. At lower concentrations, chloramphenicol delayed both growth and isoprogesterone formation by strain 144. Interestingly, rifampin partially inhibited the 16 alpha-hydroxyprogesterone dehydratase (hydration reaction) in cultures of strain 144, but did not affect the enzyme's activity in cell extracts.
Stimulation of 16-Dehydroprogesterone and progesterone reductases of Eubacterium sp. strain 144 by hemin and hydrogen or pyruvate
Appl Environ Microbiol 1985 May;49(5):1146-53.PMID:3859246DOI:10.1128/aem.49.5.1146-1153.1985.
Suspensions of Eubacterium sp. strain 144, prepared from cells grown with 16-Dehydroprogesterone, catalyzed the reduction of this steroid to 17-isoprogesterone at a very low rate. Modifications of the assay to optimize the pH (5.5) and increase the steroid solubility (10% [vol/vol] methanol) did not significantly enhance the reaction. However, growth of strain 144 in the presence of hemin was found to stimulate 16-Dehydroprogesterone reductase during the initial 30 min of incubation, giving a biphasic time course. These biphasic kinetics could be eliminated by providing the cells with an exogenous electron donor. Strain 144 used either H2 or pyruvate for this purpose, and 17-isoprogesterone formation was nearly complete after 20 to 30 min of incubation. However, under these conditions, strain 144 further converted 17-isoprogesterone to products which lacked UV absorbance (254 nm). When progesterone was used as a substrate, it was found that strain 144 could reduce the C4-C5 double bond of this steroid by a progesterone reductase to give mostly 5 beta-pregnadione and some 5 alpha-pregnadione. Furthermore, the 3-keto group of 5 beta-pregnadione steroid was also reduced to a hydroxy function. The maximum activities of both 16-Dehydroprogesterone and progesterone reductases in cell suspensions required the growth of strain 144 with hemin and 16-Dehydroprogesterone and the presence of H2 or pyruvate.
16 alpha-dehydration of corticoids by bacteria isolated from rat fecal flora
J Steroid Biochem 1982 Feb;16(2):231-7.PMID:7078162DOI:10.1016/0022-4731(82)90171-6.
Two strains (No. 144 and No. 146) of rat intestinal anaerobic bacteria, phenotypically similar to Eubacterium lentum, were isolated and found capable of 16 alpha-dehydrating corticoids. The initial step in the 16 alpha-dehydration of 16 alpha-hydroxyprogesterone was dehydration at the C-16 and C-17 position with the accumulation of 16-Dehydroprogesterone. This step required the side chain at C-17. In bacterial cultures the 16-Dehydroprogesterone was then slowly reduced to iso-progesterone. 16 alpha-Hydroxypregnanolone was also converted to iso-pregnanolone by these bacteria. 16 alpha-Dehydratase was easily demonstrated in cell fractions of strain No. 144 incubated either aerobically or anaerobically. The same extracts did not convert 16-Dehydroprogesterone to iso-progesterone under similar assay conditions. 16 alpha-Dehydration occurred at all substrate concentrations tested (20 to 200 micrograms/ml) provided the pH of the growth medium was between 6 abd 8 and the Eh below -130 mV. Strain No. 146 had both 16 alpha-dehydration and 21-dehydroxylation activities. The two enzymes functioned independently. A role for intestinal bacteria in the biotransformation of biliary 16 alpha-hydroxylated steroids and subsequent excretion in the urine is proposed.