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DBCO-Biotin - CAS 1418217-95-4

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An intermidate used for antibody-drug conjugates.

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Molecular Formula

C28H30N4O3S

Molecular Weight

502.63

DBCO-Biotin

- Specification
  - Storage
    
    Please store the product under the recommended conditions in the Certificate of Analysis.
    
    Shipping
    
    Room temperature in continental US; may vary elsewhere.
    
    IUPAC Name
    
    5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[3-(2-azatricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl)-3-oxopropyl]pentanamide
    
    Synonyms
    
    Azadibenzocyclooctyne-Biotin conjugate; N-[3-(11,12-Didehydrodibenzo[b,f]azocin-5(6H)-yl)-3-oxopropyl]-5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanamide
- Properties
  - Boiling Point
    
    905.9±65.0 °C at 760 mmHg
    
    Density
    
    1.4±0.1 g/cm3
    
    InChI Key
    
    ODZDNKWGVJPVBP-DPPGTGKWSA-N
    
    InChI
    
    InChI=1S/C28H30N4O3S/c33-25(12-6-5-11-24-27-22(18-36-24)30-28(35)31-27)29-16-15-26(34)32-17-21-9-2-1-7-19(21)13-14-20-8-3-4-10-23(20)32/h1-4,7-10,22,24,27H,5-6,11-12,15-18H2,(H,29,33)(H2,30,31,35)/t22-,24-,27-/m0/s1
    
    Canonical SMILES
    
    C1C2C(C(S1)CCCCC(=O)NCCC(=O)N3CC4=CC=CC=C4C#CC5=CC=CC=C53)NC(=O)N2
- Reference Reading
  - 1. Liposome Click Membrane Permeability Assay for Identifying Permeable Peptides
    
    Tanvi J Desai, Bahanu Habulihaz, Joe R Cannon, Arun Chandramohan, Hung Yi Kristal Kaan, Ahmad Sadruddin, Tsz Ying Yuen, Charles Johannes, Dawn Thean, Chris J Brown, David P Lane, Anthony W Partridge, Raymond Evers, Tomi K Sawyer, Jerome Hochman Pharm Res. 2021 May;38(5):843-850. doi: 10.1007/s11095-021-03005-z.Epub 2021 Mar 15.
    
    Purpose:To develop a novel, target agnostic liposome click membrane permeability assay (LCMPA) using liposome encapsulating copper free click reagent dibenzo cyclooctyne biotin (DBCO-Biotin) to conjugate azido modified peptides that may effectively translocate from extravesicular space into the liposome lumen.Method:DBCO-Biotin liposomes were prepared with egg phosphatidylcholine and cholesterol by lipid film rehydration, freeze/thaw followed by extrusion. Size of DBCO-Biotin liposomes were characterized with dynamic light scattering. Results:The permeable peptides representing energy independent mechanism of permeability showed higher biotinylation in LCMPA. Individual peptide permeability results from LCMPA correlated well with shifts in potency in cellular versus biochemical assays (i.e., cellular/ biochemical ratio) demonstrating quantitative correlation to intracellular barrier in intact cells.Conclusion:The study provides a novel membrane permeability assay that has potential to evaluate energy independent transport of diverse peptides.

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳

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