CAS 82494-09-5 Decyl-beta-D-maltopyranoside - Vaccine Lab / Alfa Chemistry

N-Decyl-beta-D-maltopyranoside for Enhanced Protein Permeability Studies in the Caco-2 model

The Caco-2 cell culture model enables sensitive detection of enhanced protein permeability in the presence of N-decyl-β-d-maltopyranoside Marušić M, et al. New Biotechnology, 2023, 30(5), 507-515.

N-Decyl-beta-D-maltopyranoside (MP C10) has been shown to enhance protein permeability in studies using the Caco-2 cell model. This case study explores its efficacy in facilitating the transepithelial transport of proteins, particularly erythropoietin, to model oral delivery of protein biopharmaceuticals.
Methods:
Four unrelated proteins were selected to test the permeability of Caco-2 monolayers. The proteins' ability to cross the epithelial model was evaluated despite their size, and their apparent permeability coefficients (Papp) were measured. Protein stability over a three-hour exposure to Caco-2 cells was also confirmed. Additionally, a cell-free setup was used to determine the upper limit of protein permeability.
Results:
All tested proteins exhibited very low Papp values of around 4 × 10^-10 cm/s, indicating minimal permeability. However, when MP C10 was introduced as an epithelium permeability enhancer, the Papp values increased dose-dependently up to approximately 1 × 10^-7 cm/s, approaching the permeability level observed in the cell-free setup. This significant enhancement suggests the involvement of the paracellular route in protein transport.
Conclusion:
The results indicate that the Caco-2 model is a suitable tool for in vitro assessment of enhanced protein permeability. The observed enhancement by MP C10, combined with the effect of specific route permeators, underscores the potential of this model for studying oral delivery of protein biopharmaceuticals.
MP C10 significantly enhances protein permeability in the Caco-2 model, making it a valuable agent for studying the oral delivery potential of protein-based drugs.

Catalog Number	ACM82494095-1
CAS	82494-09-5
Structure
Synonyms	1-O-Decyl-beta-D-maltoside
IUPAC Name	(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-Decoxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular Weight	482.6
Molecular Formula	C22H42O11
Canonical SMILES	CCCCCCCCCCOC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)O)O)O)O)O
InChI	InChI=1S/C22H42O11/c1-2-3-4-5-6-7-8-9-10-30-21-19(29)17(27)20(14(12-24)32-21)33-22-18(28)16(26)15(25)13(11-23)31-22/h13-29H,2-12H2,1H3/t13-,14-,15-,16+,17-,18-,19-,20-,21-,22-/m1/s1
InChI Key	WOQQAWHSKSSAGF-WXFJLFHKSA-N
Purity	95%+
Complexity	525
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	10
Exact Mass	482.27271215
Heavy Atom Count	33
Hydrogen Bond Acceptor Count	11
Hydrogen Bond Donor Count	7
Isomeric SMILES	CCCCCCCCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O
Monoisotopic Mass	482.27271215
Physical State	Powder
Rotatable Bond Count	14
Topological Polar Surface Area	179 Å²