17α,20β-Dihydroxy-4-pregnen-3-one
(Synonyms: 4-孕烷-17Α,20Β-二醇-3-酮,17α,20β-DHP，17α,20β-dihydroxy Progesterone) 目录号 : GC4132117α,20β-dihydroxy-4-pregnen-3-one被确认为是包括鲑科鱼类在内的多种鱼类的成熟诱导激素。
Cas No.:1662-06-2
Sample solution is provided at 25 µL, 10mM.
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17α,20β-Dihydroxy-4-pregnen-3-one was identified as the maturation-inducing hormone of several fish species, including salmonid fishes[1]. 17α,20β-Dihydroxy-4-pregnen-3-one has been widely used to promote ovulation and offspring reproduction in female fish[2].
In vitro, 17α,20β-Dihydroxy-4-pregnen-3-one treatment (30ng/ml) for 24 hours significantly inhibited testosterone (100ng/ml; 24h) stimulated 11-ketotestosterone production in testicular fragments of the common carp (Cyprinus carpio)[3]. Treatment of Japanese eel oocytes (600-700μm in diameter) with 100ng/ml of 17α,20β-Dihydroxy-4-pregnen-3-one for 24 hours significantly induced germinal vesicle breakdown[4].
In vivo, exposure to 17α,20β-dihydroxy-4-pregnen-3-one (10nM; 4h) within water induced ovulation without spawning in solitary female zebrafish and induced spawning in mixed-sex pairs of zebrafish[5]. Proliferation and differentiation of germ cells in zebrafish exposed to 100nM 17α,20β-dihydroxy-4-pregnen-3-one and 10nM estradiol for 2 weeks, with a large number of B-type spermatogonia and primary spermatocytes[6]. Intraperitoneal injection of 17α,20β-dihydroxy-4-pregnen-3-one at a dose of 900µg/kg every two days for 10 days significantly stimulated spermiation in protandrous black porgy[7].
References:
[1] Nagahama Y. 17α, 20β-Dihydroxy-4-pregnen-3-one, a maturation-inducing hormone in fish oocytes: mechanisms of synthesis and action[J]. Steroids, 1997, 62(1): 190-196.
[2] Jéhannet P, Palstra A P, Meijerhof M, et al. The induction of oocyte maturation and ovulation in the European eel (Anguilla anguilla): in vitro and in vivo comparison of progesterone with 17α, 20β-dihydroxy-4-pregnen-3-one[J]. Frontiers in Physiology, 2023, 14: 1207542.
[3] Barry T P, Aida K, Hanyu I. Effects of 17α, 20β‐dihydroxy‐4‐pregnen‐3‐one on the in vitro production of 11‐ketotestosterone by testicular fragments of the common carp, Cyprinus carpio[J]. Journal of Experimental Zoology, 1989, 251(1): 117-120.
[4] Kagawa H, Tanaka H, Ohta H, et al. In vitro effects of 17α-hydroxyprogesterone and 17α, 20β-dihydroxy-4-pregnen-3-one on final maturation of oocytes at various developmental stages in artificially matured Japanese eel Anguilla japonica[J]. Fisheries science, 1995, 61(6): 1012-1015.
[5] Knight O M, Van Der Kraak G. The role of eicosanoids in 17α, 20β-dihydroxy-4-pregnen-3-one-induced ovulation and spawning in Danio rerio[J]. General and Comparative Endocrinology, 2015, 213: 50-58.
[6] Chen S X, Bogerd J, Schoonen N E, et al. A progestin (17α, 20β-dihydroxy-4-pregnen-3-one) stimulates early stages of spermatogenesis in zebrafish[J]. General and Comparative Endocrinology, 2013, 185: 1-9.
[7] Yueh W S, Chang C F. 17α, 20β, 21-trihydroxy-4-pregnen-3-one and 17α, 20β-dihydroxy-4-pregnen-3-one stimulated spermiation in protandrous black porgy, Acanthopagrus schlegeli[J]. Fish Physiology and Biochemistry, 1997, 17(1): 187-193.
17α,20β-dihydroxy-4-pregnen-3-one被确认为是包括鲑科鱼类在内的多种鱼类的成熟诱导激素[1]。17α,20β-dihydroxy-4-pregnen-3-one已被广泛用于促进雌性鱼类的排卵和后代繁殖[2]。
在体外，30ng/ml浓度的17α,20β-dihydroxy-4-pregnen-3-one处理24小时，可显著抑制100ng/ml睾酮刺激的鲤鱼（Cyprinus carpio）睾丸碎片中11-酮基睾酮的生成[3]。使用100ng/ml的17α,20β-dihydroxy-4-pregnen-3-one处理直径600-700μm的日本鳗鲡卵母细胞24小时，能显著诱导生发泡破裂[4]。
在体内，将雌性斑马鱼暴露于10nM的17α,20β-dihydroxy-4-pregnen-3-one水溶液中4小时，可诱导排卵但不产卵，而在雌雄混养的斑马鱼中则能诱导产卵[5]。斑马鱼暴露于100nM的17α,20β-dihydroxy-4-pregnen-3-one和10nM雌二醇混合液中2周后，生殖细胞增殖和分化明显，出现大量B型精原细胞和初级精母细胞[6]。在雄性先熟的黄鳍棘鲷中，每隔两天腹腔注射900µg/kg剂量的17α,20β-dihydroxy-4-pregnen-3-one，连续10天处理能显著促进排精[7]。
| Cell experiment [1]: | |
Cell lines | Oocytes of Japanese eel |
Preparation Method | The ovarian pieces of oocytes of Japanese eel underwent dissection into smaller portions within cold culture medium before oocytes with their follicular layers got dispersed from these pieces through pipetting. The oocyte clusters were removed by forceps, and isolated oocytes were washed and transferred into the fresh incubation medium until the start of experiment. The diameter of 50 oocytes at the most advanced stage was measured under a binocular microscope. Three groups with different size oocytes (600-700μm, 700-800μm, 800-900μm in diameter) were prepared for the experiments. A total of about 30 oocytes were incubated in 24-well culture plates with 1ml of medium per well. Each group of oocytes was exposed to increasing concentrations (1, 10 and 100ng/ml) of 17a-hydroxyprogesterone and 17α,20β-Dihydroxy-4-pregnen-3-one. Controls were incubated in hormone free medium. There were three replicates made for each treatment and dosage. At the end of incubation, which was 24h at 20°C, the number of oocytes that had undergone germinal vesicle breakdown was counted. In addition, oocytes from each group were observed under a binocular microscope. Moreover, small clusters of the oocytes were also fixed in Bouin's solution, sectioned, and stained with hematoxylin and eosin to further assess the developmental stages of the oocytes. |
Reaction Conditions | 1, 10, and 100ng/ml; 24h |
Applications | 17α,20β-Dihydroxy-4-pregnen-3-one at high concentrations can induce germinal vesicle breakdown in oocytes from 600-700μm in diameter. |
| Animal experiment [2]: | |
Animal models | Adult (>90 dpf) male outbred zebrafish |
Preparation Method | To assess 17α,20β-Dihydroxy-4-pregnen-3-one-induced spermatogenesis in vivo, zebrafish were exposed in a 2-step treatment. Zebrafish were first incubated in 10nM estradiol (E2) for 3 weeks. The first treatment down-regulated testicular androgen production and blocked spermatogenesis. During the following 2 weeks, zebrafish were exposed to either 10nM E2 (control fish) or 10nM E2 + 100nM 17α,20β-Dihydroxy-4-pregnen-3-one (experimental fish). In the last 6h of the exposure period, zebrafish were transferred to a glass beaker filled with 5-bromo-2-deoxyuridine (BrdU, a marker for DNA synthesis/proliferation) at a final concentration of 3mg/ml in water environment. Zebrafish were killed by being placed in ice water, and total body weight was determined. Both testes of individual fish were removed, weighed, and the gonado-somatic index (GSI; i.e. the ratio between testis weight and body weight) was calculated. One testis was snap frozen in liquid nitrogen and stored at −80 °C. The other testis was first used for ex vivo steroid release bioassays, and then processed for morphological analysis or immunocytochemical detection of BrdU. |
Dosage form | 100nM for 2 weeks; exposure to water environment |
Applications | 17α,20β-Dihydroxy-4-pregnen-3-one treatment enhanced the testis weight, and all differentiating germ cell types, including type B spermatogonia and primary spermatocytes, were abundantly present and incorporated the DNA-synthesis marker BrdU. |
References: | |
| Cas No. | 1662-06-2 | SDF | |
| 别名 | 4-孕烷-17Α,20Β-二醇-3-酮,17α,20β-DHP，17α,20β-dihydroxy Progesterone | ||
| 化学名 | 17,20R-dihydroxy-pregn-4-en-3-one | ||
| Canonical SMILES | C[C@@H](O)[C@@]1(O)CC[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@]4(C)[C@@]3([H])CC[C@@]21C)=O | ||
| 分子式 | C21H32O3 | 分子量 | 332.5 |
| 溶解度 | 1mg/mL in ethanol, 1mg/mL in methanol, 1mg/mL in acetonitrile | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0075 mL | 15.0376 mL | 30.0752 mL |
| 5 mM | 0.6015 mL | 3.0075 mL | 6.015 mL |
| 10 mM | 0.3008 mL | 1.5038 mL | 3.0075 mL |
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动物平均体重 | g | |
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动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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2.
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