ChemicalBook CAS DataBase List 663921-15-1

663921-15-1

Name	α-amine-ω-propionic acid tetraethylene glycol
CAS	663921-15-1
EINECS(EC#)	828-940-4
Molecular Formula	C11H23NO6
MDL Number	MFCD11041129
Molecular Weight	265.3
MOL File	663921-15-1.mol

Synonyms

NH2-PEG4-COOH Amino-PEG4-COOH AMINE-PEG4-COOH Amino-PEG4-acid Amino-dPEGx-acid amino-dPEG4-acid H2N-PEG4-CH2CH2COOH NH2-PEG4-CH2CH2COOH Amino-PEG4-propionic acid 3-Amino(peg4)propionic acid Α-AMINE-Ω-PROPIONIC ACID TETRAETHYLENE GLYCOL α-amine-ω-propionic acid tetraethylene glycol 1-AMino-3,6,9,12-tetraoxapentadecan-15-oic acid 1-Amino-3,6,9,12-tetraoxa-15-pentadecanoic Acid alpha-aMine-oMega-propionic acid tetraethylene glycol 3-[2-[2-[2-(2-Aminoethoxy)ethoxy]ethoxy]ethoxy]propionic acid α-Amine-ω-propionic acid tetraethylene glycol,Amino-PEG4-acid 3-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]propanoic acid 1-Amino-3,6,9,12-tetraoxapentadecan-15-oic acid hydrochloride Propanoic acid, 3-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]- 3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid

Chemical Properties

Boiling point	409.6±40.0 °C(Predicted)
density	1.134±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,2-8°C
solubility	soluble in water
form	powder
pka	4.28±0.10(Predicted)
color	White
Appearance	white powder
InChI	InChI=1S/C11H23NO6/c12-2-4-16-6-8-18-10-9-17-7-5-15-3-1-11(13)14/h1-10,12H2,(H,13,14)
InChIKey	DKUZHSDZSMQOGQ-UHFFFAOYSA-N
SMILES	C(O)(=O)CCOCCOCCOCCOCCN

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H315-H319-H335
Precautionary statements	P280-P301+P312-P261
HS Code	2942000090

Hazard Information

Description

Amino-PEG4-acid is a very popular PEG linker. The amino group (NH2) is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The terminal carboxylic acid can react with primary amine groups of activated NHS ester to form a stable amide bond, long PEG spacer increases reagent's solubility in aqueous media.

Uses

H2N-Dpeg(4)-COOH, can be used in optical imaging of integrin αvβ3 expression with near-infrared fluorescent RGD dimer with tetra(ethylene glycol) linkers. Integrin αvβ3 plays great roles in tumor angiogenesis, invasion, and metastasis.

benefits

Amino-dPEG4-acid has a primary amine and propionic acid terminating opposite ends of a 16-atoms long (18.0 ?) polyethylene glycol (PEG) spacer. The single molecular weight PEG spacer is discrete (D = 1). Moreover, it is highly hydrophilic, and it imparts hydrophilicity to conjugates that incorporate it. Amino-dPEG4-acid is useful in many different applications, including peptide synthesis, surface modification, dendrimer construction, and small molecule modification.

reaction suitability

reaction type: Pegylations

Synthesis

581065-95-4

663921-15-1

General procedure for the synthesis of 1-amino-3,6,9,12-tetraoxapentadecan-15-oic acid tert-butyl ester from 1-amino-3,6,9,12-tetraoxapentadecan-15-oic acid: (4) 50 g of the amino end-product obtained in step (3) was dissolved in 100 mL of 3 M hydrochloric acid solution, heated to 60 °C and stirred continuously for 8 hours. Upon completion of the reaction, the pH of the reaction solution was adjusted to neutral with alkali. Subsequently, the solvent was removed by rotary evaporator and the solid obtained was separated by filtration. The filtrate was dried with anhydrous sodium sulfate and concentrated again using a rotary evaporator to finally obtain 35 g of pure product.The NMR data are shown below:

IC 50

Cleavable Linker; PEGs

References

1. Improving tumor-targeting capability and pharmacokinetics of (99m)Tc-labeled cyclic RGD dimers with PEG(4) linkers. DOI:10.1021/mp800150r
2. Short PEG-linkers improve the performance of targeted, activatable monoclonal antibody-indocyanine green optical imaging probes. DOI:10.1021/bc400050k
3. Microwave-mediated synthesis of labeled nucleotides with utility in the synthesis of DNA probes. DOI:10.1021/bc100013b
4. Improving tumor uptake and pharmacokinetics of (64)Cu-labeled cyclic RGD peptide dimers with Gly(3) and PEG(4) linkers. DOI:10.1021/bc800455p

Spectrum Detail

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