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D0260

Sigma-Aldrich

3′,5′-monofosfato cíclico de N6,2′-O-dibutiriladenosina

≥97% (HPLC), powder

Sinônimo(s):

AMP cíclico dibutirílico, Bucladesina, cAMP dibutirílico

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About This Item

Fórmula linear:
C18H23N5O8PNa
Número CAS:
16980-89-5
Peso molecular:
491.37
Número CE:
241-059-4
Número MDL:
MFCD00005843
Código UNSPSC:
41106305
ID de substância PubChem:
24893221
NACRES:
NA.77

Ensaio

≥97% (HPLC)

forma

powder

Impurezas

≤0.5% cyclic AMP and 2′-O-monobutyryl-cyclic AMP
≤3% N6-monobutyryl-cyclic AMP

cor

white

solubilidade

H2O: 100 mg/mL

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

[Na+].CCCC(=O)Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3OC(=O)CCC

InChI

1S/C18H24N5O8P.Na/c1-3-5-11(24)22-16-13-17(20-8-19-16)23(9-21-13)18-15(30-12(25)6-4-2)14-10(29-18)7-28-32(26,27)31-14;/h8-10,14-15,18H,3-7H2,1-2H3,(H,26,27)(H,19,20,22,24);/q;+1/p-1/t10-,14-,15-,18-;/m1./s1

chave InChI

KRBZRVBLIUDQNG-JBVYASIDSA-M

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Descrição geral

Dibutyrylcyclic adenosine monophosphate (cAMP) mimics the activity of endogenous cAMP.It is lipophilic, allows it to be more cell-permeable, and has higherresistance towards hydrolysis by cAMP phosphodiesterase. Dibutyryl cAMPinhibits phosphodiesterases and plays a vital role as a probe in signaltransduction pathways.

Aplicação

It has been used as a component of the differentiation medium to induce differentiationof dopaminergic neurons from floor plate progenitors. It has also been usedasa supplement in DMEM: F12 to culture neuronal cells from human pluripotent stemcells.
N6,2′-O-Dibutyryladenosine 3′,5′-cyclic monophosphate sodium salt has been used:
  • as a medium supplement for neural crest stem cells (NCSCs) differentiation
  • as a component of thawing medium for cryopreserved human iPSC (induced pluripotent stem cell)-derived neurons
  • in serum-free Dulbecco′s modified eagle′s medium (DMEM) to induce astrocyte differentiation

Ações bioquímicas/fisiológicas

Análogo de cAMP permeável à célula que ativa a proteína quinase (PKA) dependente de cAMP.

Características e benefícios

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.

Atenção

Loses 2′-O-butyryl group at pH 8.5

Outras notas

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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Differentiation of human induced pluripotent stem cell (hiPSC)-derived neurons in mouse hippocampal slice cultures
Hiragi T, et al.
Frontiers in Cellular Neuroscience, 11, 143-143 (2017)
Annagrazia Adornetto et al.
FEBS open bio, 3, 459-466 (2013-11-20)
In the central nervous system, alteration of glial cell differentiation can affect brain functions. Polychlorinated biphenyls (PCBs) are persistent environmental chemical contaminants that exert neurotoxic effects in glial and neuronal cells. We examined the effects of a commercial mixture of
Daniel Sobrido-Cameán et al.
Disease models & mechanisms, 12(2) (2019-02-03)
Classical neurotransmitters are mainly known for their roles as neuromodulators, but they also play important roles in the control of developmental and regenerative processes. Here, we used the lamprey model of spinal cord injury to study the effect of serotonin
Witold Korytowski et al.
FEBS letters, 588(1), 65-70 (2013-11-26)
StAR family proteins in vascular macrophages participate in reverse cholesterol transport (RCT). We hypothesize that under pathophysiological oxidative stress, StARs will transport not only cholesterol to macrophage mitochondria, but also pro-oxidant cholesterol hydroperoxides (7-OOHs), thereby impairing early-stage RCT. Upon stimulation
Uniaxial mechanical strain modulates the differentiation of neural crest stem cells into smooth muscle lineage on micropatterned surfaces
Li X, et al.
PLoS ONE, 6(10), e26029-e26029 (2011)
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Conteúdo relacionado

Discover Bioactive Small Molecules for Cyclic Nucleotides

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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