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D7408

2′,5′-Dideoxyadenosine

Name: 2′,5′-Dideoxyadenosine
Brand: SIGMA

≥95% (HPLC), solid

Synonym(s):

2ʹ,5ʹ-dd-Ado, NSC 95943

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₃N₅O₂

CAS Number:

6698-26-6

Molecular Weight:

235.24

MDL number:

MFCD00210904

UNSPSC Code:

41106305

PubChem Substance ID:

24894132

NACRES:

NA.77

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)

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.

Reconstitution

Store at −20 °C after reconstitution.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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

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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

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Cancer letters, 414, 268-277 (2018)

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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