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Merck
CN

B5386

Sigma-Aldrich

8-溴腺苷-3',5'-环单磷酸

≥97% (HPLC), powder, protein kinase A activator

别名:

8-Br-A-3:5-MP, 8-Br-cAMP, 8-溴-环磷酸腺苷

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About This Item

经验公式(希尔记法):
C10H11BrN5O6P
CAS号:
分子量:
408.10
Beilstein:
591930
EC 号:
MDL编号:
UNSPSC代码:
41106305
PubChem化学物质编号:
NACRES:
NA.77

product name

8-溴腺苷-3',5'-环单磷酸, ≥97% (HPLC)

质量水平

检测方案

≥97% (HPLC)

形式

powder

mp

254 °C (dec.) (lit.)

溶解性

aqueous base: soluble, clear

储存温度

−20°C

SMILES字符串

Nc1ncnc2n([C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O)c(Br)nc12

InChI

1S/C10H11BrN5O6P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,17H,1H2,(H,18,19)(H2,12,13,14)/t3-,5-,6-,9-/m1/s1

InChI key

DVKQVRZMKBDMDH-UUOKFMHZSA-N

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相关类别

应用

8-溴腺苷3′,5′-环一单磷酸用于:
  • 处理 H295R细胞,作为 CYP19诱导的阳性对照
  • 作为可渗透膜的cAMP类似物,研究其对短路电流(Isc)
  • 的影响研究其作为分化诱导剂,分化诱导Whalton′s胶质来源间充质干细胞(WJ-MSC)的潜力

生化/生理作用

8-溴腺苷-3′,5′-环单磷酸是一种细胞渗透性cAMP类似物,比cAMP具有更强的磷酸二酯酶水解抵抗性。8-溴腺苷-3′,5′-环单磷酸能激活蛋白激酶A、抑制生长、减少增殖、增加分化并诱导培养细胞的凋亡。
在平板培养肝细胞的过程中,添加8-溴腺苷3′,5′-环-单磷酸(8-溴-cAMP),有助于增加获得β-肾上腺素受体。

特点和优势

该化合物是环核苷酸研究推荐产品。点击此处 ,查看更多环核苷酸精选产品。想要了解有关生物活性小分子在其他研究领域应用的更多信息,请访问 sigma.com/discover-bsm

其他说明

8-溴腺苷-3′,5′-环单磷酸是一种膜渗透性cAMP类似物。
对光和水敏感

注意

对光和水分敏感。

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)


分析证书(COA)

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  1. How does the storage temperature relate to shipping conditions?

    The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment. See Shipping and Storage for more information.

  2. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  3. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  4. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  5. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  6. How can I solubilize 8-Bromoadenosine 3',5'-cyclic monophosphate (Product No. B5386)?

    This product is soluble in alkaline conditions. Sigma routinely tests solubility at 50 mg/ml in 1 N ammonium hydroxide.

  7. How can I store solutions of 8-Bromoadenosine 3',5'-cyclic monophosphate (Product No. B5386)?

    The solution should be stored at -20°C, protected from light and will be stable for up to 6 months.

  8. What is the difference between Product No. B5386 and Product No. B7880?

    Product No. B5386 is the free acid form of the material, while Product No. B7880 is the sodium salt. The sodium salt aids in the water solubility of the compund.  The biological function of the compounds, once dissolved, is identical.

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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Kim C H, et al.
Auris, Nasus, Larynx, 40(3), 266-272 (2013)
8-Bromo-cAMP and 8-CPT-cAMP Increase the Density of beta-Adrenoceptors in Hepatocytes by a Mechanism Not Mimicking the Effect of cAMP
Sandnes D, et al.
Pharmacology & Toxicology, 79(1), 15-22 (1996)
Differentiation of human umbilical cord Wharton?s jelly-derived mesenchymal stem cells into endometrial cells
Shi Q, et al.
Stem Cell Research & Therapy, 8(1), 246-246 (2017)
2, 3, 7, 8-Tetrachlorodibenzo-p-dioxin and diindolylmethanes differentially induce cytochrome P450 1A1, 1B1, and 19 in H295R human adrenocortical carcinoma cells
Sanderson J T, et al.
Toxicological Sciences, 61(1), 40-48 (2001)
Akihiro Goto et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(11), 4901-4912 (2013-03-15)
Enteric neural crest-derived cells (ENCCs) migrate from the anterior foregut in a rostrocaudal direction to colonize the entire gastrointestinal tract and to form the enteric nervous system. Genetic approaches have identified many signaling molecules regulating the migration of ENCCs; however

商品

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

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