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A4308

Sigma-Aldrich

Autocamtide 2-related inhibitory peptide

≥97% (HPLC), lyophilized powder

Synonyme(s) :

[Ala9]-Autocamtide 2, AIP

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About This Item

Formule empirique (notation de Hill):
C64H116N22O19
Numéro CAS:
Poids moléculaire :
1497.74
Code UNSPSC :
12352202
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Source biologique

synthetic

Pureté

≥97% (HPLC)

Forme

lyophilized powder

Poids mol.

~_1.5 kDa

Composition

Peptide content, ≥70%

Solubilité

H2O: soluble

Température de stockage

−20°C

Chaîne 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

Clé InChI

COEHZSYVSXUBHI-CYZNULJVSA-N

Amino Acid Sequence

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

Application

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


Certificats d'analyse (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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