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A4308

Sigma-Aldrich

Autocamtide 2-related inhibitory peptide

≥97% (HPLC), lyophilized powder

Sinônimo(s):

[Ala9]-Autocamtide 2, AIP

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About This Item

Fórmula empírica (Notação de Hill):
C64H116N22O19
Número CAS:
Peso molecular:
1497.74
Código UNSPSC:
12352202
ID de substância PubChem:
NACRES:
NA.77

fonte biológica

synthetic

Ensaio

≥97% (HPLC)

forma

lyophilized powder

peso molecular

~_1.5 kDa

composição

Peptide content, ≥70%

solubilidade

H2O: soluble

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](CC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)CC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CCCCN)C(C)C)C(O)=O

InChI

1S/C65H114N20O21/c1-32(2)28-46(63(105)106)85-54(96)36(7)78-62(104)45(31-52(93)94)84-56(98)38(33(3)4)30-47(86)34(5)76-59(101)43(19-22-50(89)90)81-55(97)37(18-21-49(69)88)29-48(87)40(16-12-26-74-64(70)71)79-60(102)42(17-13-27-75-65(72)73)83-61(103)44(20-23-51(91)92)80-53(95)35(6)77-58(100)41(15-9-11-25-67)82-57(99)39(68)14-8-10-24-66/h32-46H,8-31,66-68H2,1-7H3,(H2,69,88)(H,76,101)(H,77,100)(H,78,104)(H,79,102)(H,80,95)(H,81,97)(H,82,99)(H,83,103)(H,84,98)(H,85,96)(H,89,90)(H,91,92)(H,93,94)(H,105,106)(H4,70,71,74)(H4,72,73,75)/t34-,35-,36-,37+,38-,39-,40-,41-,42-,43-,44-,45-,46-/m0/s1

chave InChI

COEHZSYVSXUBHI-CYZNULJVSA-N

Amino Acid Sequence

Lys-Lys-Ala-Leu-Arg-Arg-Gln-Glu-Ala-Val-Asp-Ala-Leu

Aplicação

Autocamtide 2-related inhibitory peptide has been used:
  • To inhibit calmodulin kinase II (CaMKII) action in virulent Theileria infected macrophages
  • To study its influence on oxidative stress associated with neural cell death after hypoxia-ischemia, using neonatal hippocampal slice cultures
  • To quench the phosphorylation of recombinant synGA (GTPase-activating protein) induced by CaMKII

Ações bioquímicas/fisiológicas

Calmodulin kinase II facilitates the calcium-dependent L-type calcium channels. Autocamtide 2-related inhibitory peptide action does not influence cAMP (cyclic adenosine monophosphate)-dependent protein kinase II, calmodulin-dependent protein kinase IV and protein kinase C. Increased expression of calmodulin kinase II is observed in structural heart disease, indicated by myocardial infarction. Thus, inhibition of calmodulin kinase II activity might serve as a protective effect against structural heart disease, as it is found to prevent cardiac hypertrophy, dilation and dysfunction.
Potent inhibitor of calmodulin-depentent protein kinase II.

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

Eyeshields, Gloves, type N95 (US)


Certificados de análise (COA)

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Calmodulin kinase II inhibition protects against structural heart disease
Zhang R, et al.
Nature Medicine, 11(4), 409-409 (2005)
A Ishida et al.
Biochemical and biophysical research communications, 212(3), 806-812 (1995-07-26)
A novel synthetic peptide AIP (autocamtide-2-related inhibitory peptide), a nonphosphorylatable analog of autocamtide-2, was found to be a highly specific and potent inhibitor of calmodulin-dependent protein kinase II (CaM-kinase II). It was 50 and 500 times more potent than CaMK-(281-302Ala286)
Calmodulin Kinase II Is Involved in Voltage-dependent Facilitation of the L-type Cav1. 2 Calcium Channel IDENTIFICATION OF THE PHOSPHORYLATION SITES
Lee TS, et al.
The Journal of Biological Chemistry, 281(35), 25560-25567 (2006)
Proteins Peptides and Amino Acids SourceBook, 486-486 (2002)
Phosphorylation of synaptic GTPase-activating protein (synGAP) by Ca2+/calmodulin-dependent protein kinase II (CaMKII) and cyclin-dependent kinase 5 (CDK5) alters the ratio of its GAP activity toward Ras and Rap GTPases
Walkup WG, et al.
The Journal of Biological Chemistry, 290(8), 4908-4927 (2015)

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