D7408

2′,5′-Dideoxyadenosine

Name: 2&#8242;,5&#8242;-Dideoxyadenosine
Brand: SIGMA
Price: 1420 PLN

≥95% (HPLC), Adenylyl cyclase inhibitor, solid

Synonym(s):

2ʹ,5ʹ-dd-Ado, NSC 95943

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D7408-5MG

PLN 1,420.00

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₃N₅O₂

CAS Number:

6698-26-6

Molecular Weight:

235.24

UNSPSC Code:

41106305

PubChem Substance ID:

24894132

NACRES:

NA.77

MDL number:

MFCD00210904

Assay:

≥95% (HPLC)

Form:

solid

Quality level:

100

Key Documents

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Product Name

2′,5′-Dideoxyadenosine, ≥95% (HPLC), solid

Quality Level

100

assay

≥95% (HPLC)

form

solid

color

white

solubility

DMSO: soluble

storage temp.

−20°C

SMILES string

C[C@H]1O[C@H](C[C@@H]1O)n2cnc3c(N)ncnc23

InChI

1S/C10H13N5O2/c1-5-6(16)2-7(17-5)15-4-14-8-9(11)12-3-13-10(8)15/h3-7,16H,2H2,1H3,(H2,11,12,13)/t5-,6+,7-/m1/s1

InChI key

FFHPXOJTVQDVMO-DSYKOEDSSA-N

Gene Information

rat ... Adcy2(81636)

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Show Differences

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This Item	288104	D8190	D1068
Sigma-Aldrich D7408 2′,5′-Dideoxyadenosine	Sigma-Aldrich 288104 2′,5′-Dideoxyadenosine	Sigma-Aldrich D8190 3′,4′-Dichlorobenzamil hydrochloride	Sigma-Aldrich D1068 DCB
form solid	form solid	form solid	form solid
assay ≥95% (HPLC)	assay ≥98% (HPLC)	assay >98% (HPLC)	assay ≥98% (HPLC)
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. −20°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C
solubility DMSO: soluble	solubility DMSO: 10 mg/mL	solubility DMSO: soluble 30 mg/mL, H₂O: insoluble	solubility DMSO: ~6.8 mg/mL, H₂O: insoluble
color white	color white	color yellow	color yellow

Application

2′,5′-Dideoxyadenosine has been used to elucidate the mechanism of diligustilide (DLG). It has also been used to inhibit adenylate cyclase (AC).

Biochem/physiol Actions

Cell-permeable adenylyl cyclase inhibitor. IC₅₀ = 2.7 μM in detergent-dispersed rat brain preparations.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Adenylyl cyclases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

Store at −20 °C after reconstitution.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Prostaglandin E(2) protects human lung fibroblasts from cigarette smoke extract-induced apoptosis via EP(2) receptor activation.

Hisatoshi Sugiura et al.

Journal of cellular physiology, 210(1), 99-110 (2006-09-26)

Prostaglandin E(2) (PGE(2)) has been shown to have a strong cytoprotective effect, inhibiting apoptosis. In the present study, we evaluated whether PGE(2) has a protective effect on cigarette smoke extract (CSE)-induced apoptosis in human lung fibroblasts. Apoptosis was assessed by

Cyclic AMP signaling contributes to neural plasticity and hyperexcitability in AH sensory neurons following intestinal Trichinella spiralis-induced inflammation.

Zhixiong Chen et al.

International journal for parasitology, 37(7), 743-761 (2007-02-20)

Trichinella spiralis infection causes hyperexcitability in enteric after-hyperpolarising (AH) sensory neurons that is mimicked by neural, immune or inflammatory mediators known to stimulate adenylyl cyclase (AC)/cyclic 3',5'-adenosine monophosphate (cAMP) signaling. The hypothesis was tested that ongoing modulation and sustained amplification

Elevated cyclic AMP levels promote BRAFCA/Pten-/- mouse melanoma growth but pCREB is negatively correlated with human melanoma progression

Rodriguez CI, et al.

Cancer letters, 414, 268-277 (2018)

Cyclooxygenase-2 induction by bradykinin in aortic vascular smooth muscle cells.

Jorge A Rodriguez et al.

American journal of physiology. Heart and circulatory physiology, 290(1), H30-H36 (2005-09-07)

Vascular smooth muscle cell proliferation and migration play an important role in the pathophysiology of several vascular diseases, including atherosclerosis. Prostaglandins that have been implicated in this process are synthesized by two isoforms of cyclooxygenase (COX), with the expression of

Evidence for multiple distinctly localized adenylyl cyclase isoforms in mammalian spermatozoa.

Rhona W Baxendale et al.

Molecular reproduction and development, 66(2), 181-189 (2003-09-02)

In addition to a bicarbonate-regulated soluble adenylyl cyclase (sAC), mammalian spermatozoa, like somatic cells, appear to contain receptor/G protein-regulated AC activity that contributes to the modulation of specialized cell processes. This study provides evidence that agents, known to influence somatic

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