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R6520

Sigma-Aldrich

Rolipram

≥98% (HPLC), solid, cAMP-specific phosphodiesterase (PDE4) inhibitor

Sinônimo(s):

4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone, ZK 62711

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About This Item

Fórmula empírica (Notação de Hill):
C16H21NO3
Número CAS:
61413-54-5
Peso molecular:
275.34
Número CE:
262-771-1
Número MDL:
MFCD00270906
Código UNSPSC:
41106305
ID de substância PubChem:
24278196
NACRES:
NA.77

Nome do produto

Rolipram, solid, ≥98% (HPLC)

fonte biológica

synthetic (organic)

Ensaio

≥98% (HPLC)

Formulário

solid

cor

white to off-white

solubilidade

H2O: 0.2 mg/mL
ethanol: 7 mg/mL
DMSO: 7.3 mg/mL

cadeia de caracteres SMILES

COc1ccc(cc1OC2CCCC2)C3CNC(=O)C3

InChI

1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)

chave InChI

HJORMJIFDVBMOB-UHFFFAOYSA-N

Informações sobre genes

human ... LITAF(9516) , PDE3A(5139) , PDE4A(5141) , PDE4B(5142) , PDE4C(5143) , PDE4D(5144) , PDE5A(8654) , PDE7A(5150)
mouse ... Pde4a(18577)
rat ... Adora1(29290) , Pde1b(29691) , Pde2a(81743) , Pde3a(50678) , Pde4a(25638) , Pde4b(24626) , Pde4c(290646) , Pde5a(171115)

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Descrição geral

Rolipram enhances tissue protection, anatomical repair and functional recovery. It is used to treat asthma, arthritis, Huntington′s disease and multiple sclerosis. Rolipram inhibits injury-induced reductions in cyclic AMP, which is associated with acute central nervous system injury. It functions as an antidepressant, stimulates neurite outgrowth and axonal regeneration in the presence of myelin inhibitors.

Aplicação

Rolipram has been used:
  • to investigate its effects on testicular torsion–detorsion injury(36)
  • to block the effects of phosphodiesterase-4 (PDE4)(37)
  • as a component in chemically induced long-term potentiation (cLTP) induction media(38)

Ações bioquímicas/fisiológicas

Selective cAMP-specific phosphodiesterase (PDE4) inhibitor.

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

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
095M4738V
085M4740V
033M4738V
011M4606V
118K4610

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CNS Regeneration: Basic Science and Clinical Advances (2011)
Luís M Costa et al.
Behavioural brain research, 243, 66-73 (2013-01-09)
Numerous animal model studies in the past decade have demonstrated that pharmacological elevation of cyclic AMP (cAMP) alone, or in combination with other treatments, can promote axonal regeneration after spinal cord injury. Elevation of cAMP via the phosphodiesterase 4 (PDE4)
Raehannah J Jamshidi et al.
The Journal of pharmacology and experimental therapeutics, 359(2), 319-328 (2016-10-21)
A single administration of the κ opioid receptor (KOR) antagonist, norbinaltorphimine (norBNI), produces long-term reduction in KOR function in heterologous expression systems and brain that is mediated by activation of c-Jun N-terminal kinase (JNK). In this study, we examined the
Dong Yan et al.
The Journal of pharmacology and experimental therapeutics, 366(1), 220-236 (2018-04-15)
The contribution of gene expression changes to the adverse and therapeutic effects of β2-adrenoceptor agonists in asthma was investigated using human airway epithelial cells as a therapeutically relevant target. Operational model-fitting established that the long-acting β2-adrenoceptor agonists (LABA) indacaterol, salmeterol
Hao Huang et al.
Acta pharmacologica Sinica, 37(12), 1543-1554 (2016-09-27)
Phosphodiesterase 4 (PDE4) isozymes are involved in different functions, depending on their patterns of distribution in the brain. The PDE4 subtypes are distributed in different inflammatory cells, and appear to be important regulators of inflammatory processes. In this study we
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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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