t-boc-N-amido-PEG4-NHS ester - CAS 859230-20-9

t-boc-N-amido-PEG4-NHS ester - CAS 859230-20-9 Catalog number: BADC-00693

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t-Boc-N-amido-PEG4-NHS ester is a PEG derivative containing an NHS ester and a Boc-protected amino group. The Boc group can be deprotected under mild acidic conditions to form the free amine. The NHS ester can be used to label the primary amines (-NH2) of proteins, amine-modified oligonucleotides, and other amine-containing molecules. PEG Linkers may be useful in the development of antibody drug conjugates.

Category
ADCs Linker
Product Name
t-boc-N-amido-PEG4-NHS ester
CAS
859230-20-9
Catalog Number
BADC-00693
Molecular Formula
C20H34N2O10
Molecular Weight
462.49
t-boc-N-amido-PEG4-NHS ester

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Description
t-Boc-N-amido-PEG4-NHS ester is a PEG derivative containing an NHS ester and a Boc-protected amino group. The Boc group can be deprotected under mild acidic conditions to form the free amine. The NHS ester can be used to label the primary amines (-NH2) of proteins, amine-modified oligonucleotides, and other amine-containing molecules. PEG Linkers may be useful in the development of antibody drug conjugates.
Synonyms
5,8,11,14-Tetraoxa-2-azaheptadecanedioic acid, 1-(1,1-dimethylethyl) 17-(2,5-dioxo-1-pyrrolidinyl) ester; BocNH-PEG4-CH2CH2COONH; Boc-NH-PEG4-NHS ester; 2,5-Dioxopyrrolidin-1-yl 2,2-dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azaicosan-20-oate; 2-Methyl-2-propanyl {15-[(2,5-dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}carbamate; Carbamic acid, N-[15-[(2,5-dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl]-, 1,1-dimethylethyl ester
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Canonical SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCOCCC(=O)ON1C(=O)CCC1=O
InChI
InChI=1S/C20H34N2O10/c1-20(2,3)31-19(26)21-7-9-28-11-13-30-15-14-29-12-10-27-8-6-18(25)32-22-16(23)4-5-17(22)24/h4-15H2,1-3H3,(H,21,26)
InChIKey
HHPGGUMKDXTEDQ-UHFFFAOYSA-N
Density
1.2±0.1 g/cm3
Solubility
Soluble in DCM, DMF, DMSO
Appearance
Pale Yellow or Colorless Oily Liquid
Purity
>95%
Shipping
Room temperature
Storage
Store at 2-8°C
1.A PEG-Fmoc conjugate as a nanocarrier for paclitaxel
Zhang P, Huang Y, Liu H, Marquez RT, Lu J, Zhao W, Zhang X, Gao X, Li J, Venkataramanan R, Xu L, Li S.
We report here that a simple, well-defined, and easy-to-scale up nanocarrier, PEG5000-lysyl-(α-Fmoc-ε-t-Boc-lysine)2 conjugate (PEG-Fmoc), provides high loading capacity, excellent formulation stability and low systemic toxicity for paclitaxel (PTX), a first-line chemotherapeutic agent for various types of cancers. 9-Fluorenylmethoxycarbonyl (Fmoc) was incorporated into the nanocarrier as a functional building block to interact with drug molecules. PEG-Fmoc was synthesized via a three-step synthetic route, and it readily interacted with PTX to form mixed nanomicelles of small particle size (25-30 nm). The PTX loading capacity was about 36%, which stands well among the reported micellar systems. PTX entrapment in this micellar system is achieved largely via an Fmoc/PTX π-π stacking interaction, which was demonstrated by fluorescence quenching studies and (13)C NMR. PTX formulated in PEG-Fmoc micelles demonstrated sustained release kinetics, and in vivo distribution study via near infrared fluorescence imaging demonstrated an effective delivery of Cy5.5-labled PTX to tumor sites. The maximal tolerated dose for PTX/PEG-Fmoc (MTD > 120 mg PTX/kg) is higher than those for most reported PTX formulations, and in vivo therapeutic study exhibited a significantly improved antitumor activity than Taxol, a clinically used formulation of PTX. Our system may hold promise as a simple, safe, and effective delivery system for PTX with a potential for rapid translation into clinical study.
2.Tailored PEG for rh-G-CSF analogue site-specific conjugation
Salmaso S, Bersani S, Scomparin A, Mastrotto F, Scherpfer R, Tonon G, Caliceti P.
A new end-tailored monomethoxypoly(ethylene glycol) (PEG) for site-directed protein conjugation was synthesized according to a three-step procedure: (1) linear 20 kDa PEG-NH(2) was conjugated to 12-(Boc-amino)dodecanoic acid; (2) PEG-NHCO(CH(2))(11)-Boc was deprotected by TFA treatment; (3) PEG-NHCO(CH(2))(11)-NH(2) was conjugated to 6-maleimidohexanoic acid to yield PEG-NHCO-(CH(2))(11)-NHCO(CH(2))(5)-Mal (PEG-C(18)-Mal). The chemical intermediates as well as the final product were purified by solvent precipitation/extraction and characterized by (1)H NMR spectroscopy and colorimetric analysis. The synthesis procedure yielded over 90% activated product [PEG-NHCO-(CH(2))(11)-NHCO(CH(2))(5)-Mal/PEG-NH(2) molar ratio, %]. Both PEG-C(18)-Mal and the commercial maleimido activated 20 kDa linear PEG (PEG-Mal) were used for conjugation to (17)Cys of recombinant human granulocyte colony stimulating factor (rh-G-CSF). Under denaturing conditions, at pH 7.0, both activated PEGs yielded over 90% protein conjugation. Under native conditions, about 55% and 7% PEGylated protein were obtained with PEG-C(18)-Mal and PEG-Mal, respectively. Circular dichroism analysis showed that the PEGylation does not induce detectable alteration of the protein secondary structure. On the other hand, the PEGylation conditions were found to affect significantly the protein stability. The derivatives obtained either with the two polymers by unfolding/refolding process or with PEG-Mal under native conditions displayed rapid aggregation with half-life ranging from 30 to 90 min. The derivative obtained with PEG-NHCO-(CH(2))(11)-NHCO(CH(2))(5)-Mal in the absence of guanidinium chloride displayed remarkably higher stability with aggregation half-life of about 60 h.
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