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764019

Sigma-Aldrich

Dibenzocyclooctyne-PEG4-N-hydroxysuccinimidyl ester

≥90%

Synonym(s):

DBCO-PEG4-NHS ester, DBCO-PEG4-SE, DBCO-PEG4-succinimidyl ester

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About This Item

Empirical Formula (Hill Notation):
C34H39N3O10
Molecular Weight:
649.69
MDL number:
MFCD26793797
UNSPSC Code:
12352108
PubChem Substance ID:
329767092
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

Assay

≥90%

form

paste

reaction suitability

reaction type: click chemistry
reagent type: linker

functional group

NHS ester

storage temp.

−20°C

SMILES string

O=C(CCC(NCCOCCOCCOCCOCCC(ON1C(CCC1=O)=O)=O)=O)N2CC3=C(C=CC=C3)C#CC4=C2C=CC=C4

InChI

1S/C34H39N3O10/c38-30(11-12-31(39)36-25-28-7-2-1-5-26(28)9-10-27-6-3-4-8-29(27)36)35-16-18-44-20-22-46-24-23-45-21-19-43-17-15-34(42)47-37-32(40)13-14-33(37)41/h1-8H,11-25H2,(H,35,38)

InChI key

RRCXYKNJTKJNTD-UHFFFAOYSA-N

Related Categories

Application

Dibenzocyclooctyne-PEG4-N-hydroxysuccinimidyl ester may be used in the synthesis of a prostate-specific membrane antigen (PSMA)-targeted single photon emission computed tomography (SPECT) agent via copper-less click chemistry.[1]
Succinimidyl ester (NHS, amine reactive) functionalized cyclooctyne derivative for incorporation of the cyclooctyne moiety into amine containing compounds or biomolecules. Cyclooctynes are useful in strain-promoted copper-free click chemistry cycloaddition reactions. This dibenzocyclooctyne will react with azide functionalized compounds or biomolecules without the need for a Cu(I) catalyst to result in a stable triazole linkage.

Applications Include:
  • Protein-peptide conjugates
  • Antibody-enzyme or antibody-drug conjugates
  • Protein or peptide-oligonucleotide conjugates
  • Surface modification

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX4539
MKCX3189
MKCX2146
MKCX2100
MKCX2101

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Matthias Krumb et al.
Cells, 9(9) (2020-09-17)
Herein, we report the synthesis of carbohydrate and glycodendron structures for dendritic cell targeting, which were subsequently bound to hydroxyethyl starch (HES) nanocapsules prepared by the inverse miniemulsion technique. The uptake of the carbohydrate-functionalized HES nanocapsules into immature human dendritic
PSMA?targeted SPECT agents: Mode of binding effect on in vitro performance.
Nedrow?Byers JR, et al.
Prostate, 73(4), 355-362 (2013)
Yayu Wang et al.
International journal of nanomedicine, 15, 7967-7977 (2020-10-30)
Current drugs used for osteoporosis therapy show strong adverse effects. Stem cell-derived extracellular vesicles (EVs) provide another choice for osteoporosis therapy. Mouse mesenchymal stem cells (mMSCs)-derived EVs promote bone regeneration; however, their clinical application is limited due to non-specific tissue
Seong Ho Kim et al.
ACS nano, 11(9), 9352-9359 (2017-08-29)
Reversible regulation of enzyme activity by chemical and physical stimuli is often achieved by incorporating stimuli-responsive domains in the enzyme of interest. However, this method is suitable for a limited number of enzymes with well-defined structural and conformational changes. In
Hong Pan et al.
Biomaterials, 181, 199-209 (2018-08-08)
Enterovirus 71 (EV71), the major pathogen of hand-foot-and-mouth disease (HFDM), can cause severe neurological and respiratory manifestations in young children. Viral spread route and tissue tropism are key factors contributing to different pathogenicity of EV71, however it remains a challenge
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Questions

1–4 of 4 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. Hi I would like to know if the extinction coefficient value of this molecule available. Thanks

    1 answer

    1. There is no published value for the extinction coefficient of this molecule.

      Helpful?

  4. Hi. Is this product stable at 4 degrees for a few days? Thanks

    1 answer

    1. The storage temperature is deliberately conservative for long term storage and is set at -20°C for this item. Unfortunately, storage at alternate conditions such as 4°C have not been assessed for this product.

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