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Key Documents

Safety Information

SML0612

Sigma-Aldrich

Perifosine

≥98% (HPLC)

Synonym(s):

4-[[Hydroxy(octadecyloxy)phosphinyl]oxy]-1,1-dimethyl-piperidinium inner salt, KRX-0401, Octadecyl-(1,1-dimethyl-4-piperidylio) phosphate

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About This Item

Empirical Formula (Hill Notation):
C25H52NO4P
CAS Number:
157716-52-4
Molecular Weight:
461.66
UNSPSC Code:
12352200
NACRES:
NA.77
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Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 10 mg/mL, clear

shipped in

wet ice

storage temp.

−20°C

SMILES string

[P](=O)([O-])(OC1CC[N+](CC1)(C)C)OCCCCCCCCCCCCCCCCCC

InChI

1S/C25H52NO4P/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24-29-31(27,28)30-25-20-22-26(2,3)23-21-25/h25H,4-24H2,1-3H3

InChI key

SZFPYBIJACMNJV-UHFFFAOYSA-N

Compare Similar Items

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Show Differences

1 of 4

This Item
SML1662S4257SML1142
Perifosine ≥98% (HPLC)

SML0612

Perifosine

Buparvaquone ≥98% (HPLC)

SML1662

Buparvaquone

Sphingosylphosphorylcholine ≥98%, powder

S4257

Sphingosylphosphorylcholine

VU0071063 ≥98% (HPLC)

SML1142

VU0071063

form

powder

form

powder

form

powder

form

powder

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

solubility

H2O: 10 mg/mL, clear

solubility

DMSO: soluble, chloroform: soluble

solubility

chloroform/methanol (2:1): complete 10 mg/ml, clear to slightly hazy, colorless to light yellow

solubility

DMSO: 10 mg/mL, clear

shipped in

wet ice

shipped in

-

shipped in

-

shipped in

-

Application

Perifosine has been used as an alkyl phospholipid AKT inhibitor.[1]

Biochem/physiol Actions

Perifosine (KRX-0401) is a selective bioavailable alkylphospholipid inhibitor of protein kinase B/Akt (PKB/Akt) with anti-proliferative activity.
Perifosine (KRX-0401) is a selective bioavailable alkylphospholipid inhibitor of protein kinase B/Akt (PKB/Akt) with anti-proliferative activity. Perifosine acts on cell membranes, selectively targeting proliferating cells, inducing growth arrest and apoptosis.
Perifosine (octadecyl-(1,1-dimethyl-4-piperidylio)) is an antitumor compound. It acts at lipid rafts and stops lysosomal accumulation and mTORC1 (mammalian target of rapamycin complex 1) signaling.[1] This drug exhibits significant antiproliferative activity in vitro and in vivo in various human cancer model systems.[2]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000344624
    0000344624
    0000175923
    0000175923
    0000140957

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    Perifosine, a novel alkylphospholipid, inhibits protein kinase B activation.
    Kondapaka SB, et al.
    Molecular Cancer Therapeutics, 2(11), 1093-1103 (2003)
    TUFT1 interacts with RABGAP1 and regulates mTORC1 signaling.
    Kawasaki N, et al.
    Cell discovery, 4(1), 1-1 (2018)
    Natsumi Kawasaki et al.
    Cell discovery, 4, 1-1 (2018-02-10)
    The mammalian target of rapamycin (mTOR) pathway is commonly activated in human cancers. The activity of mTOR complex 1 (mTORC1) signaling is supported by the intracellular positioning of cellular compartments and vesicle trafficking, regulated by Rab GTPases. Here we showed
    Junghyun Yoon et al.
    Nucleic acids research, 52(9), 5088-5106 (2024-02-27)
    Exploring the connection between ubiquitin-like modifiers (ULMs) and the DNA damage response (DDR), we employed several advanced DNA damage and repair assay techniques and identified a crucial role for LC3B. Notably, its RNA recognition motif (RRM) plays a pivotal role
    José M Bravo-San Pedro et al.
    Cell metabolism, 30(4), 754-767 (2019-08-20)
    Autophagy facilitates the adaptation to nutritional stress. Here, we show that short-term starvation of cultured cells or mice caused the autophagy-dependent cellular release of acyl-CoA-binding protein (ACBP, also known as diazepam-binding inhibitor, DBI) and consequent ACBP-mediated feedback inhibition of autophagy.
    View All Related Papers

    Protocols

    PKB/Akt

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