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A4308

Sigma-Aldrich

Autocamtide 2-related inhibitory peptide

≥97% (HPLC), lyophilized powder

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Synonym(s):
[Ala9]-Autocamtide 2, AIP
Empirical Formula (Hill Notation):
C64H116N22O19
CAS Number:
Molecular Weight:
1497.74
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic

Quality Level

assay

≥97% (HPLC)

form

lyophilized powder

mol wt

~_1.5 kDa

composition

Peptide content, ≥70%

solubility

H2O: soluble

storage temp.

−20°C

SMILES string

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

InChI key

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

Biochem/physiol Actions

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

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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)
Calmodulin kinase II inhibition protects against structural heart disease
Zhang R, et al.
Nature Medicine, 11(4), 409-409 (2005)
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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