DBCO-Biotin

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Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

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

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

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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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂