Name: 6-O-a-Maltosyl-b-cyclodextrin
SKU: CD104723606
Rating: 5 (1 reviews)

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6-O-a-Maltosyl-b-cyclodextrin

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Catalog Number	CD104723606
CAS	104723-60-6
Structure	https://resource.alfachemic.com/structure/104723-60-6.gif
Synonyms	Maltosyl-Β-Cd
IUPAC Name	(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-10-[[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-5,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
Molecular Weight	1459.27g/mol
Molecular Formula	C54H90O45
InChI	InChI=1S/C54H90O45/c55-1-10-19(63)20(64)29(73)47(83-10)92-38-11(2-56)84-46(30(74)21(38)65)82-9-18-45-28(72)37(81)54(91-18)98-44-17(8-62)89-52(35(79)26(44)70)96-42-15(6-60)87-50(33(77)24(42)68)94-40-13(4-58)85-48(31(75)22(40)66)93-39-12(3-57)86-49(32(76)23(39)67)95-41-14(5-59)88-51(34(78)25(41)69)97-43-16(7-61)90-53(99-45)36(80)27(43)71/h10-81H,1-9H2/t10-,11-,12-,13-,14-,15-,16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46+,47-,48?,49-,50-,51-,52-,53-,54-/m1/s1
InChI Key	QFSFPJHBIGWPMD-PBVGKYIBSA-N
Purity	95+%
Appearance	White to off-white powder
Storage	Stored at 2°C - 8°C
Isomeric SMILES	C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](O[C@@H]([C@@H]([C@H]2O)O)OC[C@@H]3[C@@H]4[C@@H]([C@H]([C@H](O3)O[C@@H]5[C@H](O[C@@H]([C@@H]([C@H]5O)O)O[C@@H]6[C@H](O[C@@H]([C@@H]([C@H]6O)O)O[C@@H]7[C@H](OC([C@@H]([C@H]7O)O)O[C@@H]8[C@H](O[C@@H]([C@@H]([C@H]8O)O)O[C@@H]9[C@H](O[C@@H]([C@@H]([C@H]9O)O)O[C@@H]1[C@H](O[C@H](O4)[C@@H]([C@H]1O)O)CO)CO)CO)CO)CO)CO)O)O)CO)O)O)O)O
Packaging	1g

Case Study

6-O-α-Maltosyl-β-cyclodextrin for Lysosomal Cholesterol Efflux in Npc1-Deficient CHO Cells

Role of 6-O-α-maltosyl-β-cyclodextrin in lysosomal cholesterol deprivation in Npc1-deficient Chinese hamster ovary cells Okada Y, et al. Carbohydrate Research, 2018, 455, 54-61.

6-O-α-Maltosyl-β-cyclodextrin (Mal-βCD) was investigated for its role in facilitating lysosomal cholesterol efflux in Npc1-deficient Chinese hamster ovary (CHO) cells. Using LC/MS and LC/MS/MS, researchers quantitatively assessed the intracellular trafficking of Mal-βCD and its effects on cholesterol dynamics. Mal-βCD was efficiently endocytosed by Npc1-mutant CHO-JP17 cells and localized within lysosomes, where it underwent partial metabolic conversion to 6-O-α-glucosyl-β-cyclodextrin (Glc-βCD). These cyclodextrins-Mal-βCD and its Glc-βCD metabolite-subsequently facilitated the mobilization and extracellular release of unesterified cholesterol. In contrast, Mal-βCD did not directly penetrate isolated lysosomes from homogenized cells, indicating that its lysosomal accumulation was endocytosis-dependent. The study provided direct evidence, via mass spectrometric quantification, of the coupled efflux of cyclodextrins and cholesterol into the extracellular medium.

6-O-α-Maltosyl-β-cyclodextrin for Modulating Cellular Cholesterol and ABC Transporter Expression in P-815 Cells

Effect of 6-O-α-maltosyl-β cyclodextrin and its cholesterol inclusion complex on cellular cholesterol levels and ABCA1 and ABCG1 expression in mouse mastocytoma P-815 cells Okada Y, et al. Carbohydrate Research, 2012, 357, 68-74

6-O-α-maltosyl-β-cyclodextrin (Mal-βCD) was employed to investigate its role in modulating intracellular cholesterol levels and the expression of ATP-binding cassette (ABC) transporters in mouse mastocytoma P-815 cells. Mal-βCD, known for its ability to form soluble inclusion complexes with cholesterol, was used both in its free form and as a pre-formed cholesterol complex (CLM) to study cholesterol depletion and replenishment. Cellular cholesterol content was quantitatively assessed using liquid chromatography-mass spectrometry (LC/MS) and visualized through filipin III fluorescence microscopy. Mal-βCD effectively extracted cholesterol from P-815 cells, while cholesterol replenishment was achieved using CLM without inducing cytotoxicity.
Uptake studies demonstrated that CLM was internalized more efficiently than free Mal-βCD or free cholesterol, and the uptake was inhibited at low temperature and in the presence of metabolic inhibitors (sodium azide and cytochalasin D), indicating an energy-dependent process. Western blotting and RT-PCR confirmed that Mal-βCD-mediated cholesterol depletion downregulated ABCA1 and ABCG1 expression, whereas cholesterol reloading via CLM restored their expression. Notably, P-glycoprotein (P-gp) expression and activity remained unaffected, as confirmed by rhodamine 123 efflux assays.

6-O-α-Maltosyl-β-cyclodextrin for the Regulation of Lipid Metabolism in Npc1-Deficient CHO Cells

Effects of 6-O-α-maltosyl-β cyclodextrin on lipid metabolism in Npc1-deficient Chinese hamster ovary cells Okada Y, et al. Molecular Genetics and Metabolism, 2022, 137(3), 239-248.

6-O-α-maltosyl-β-cyclodextrin (Mal-βCD) was evaluated for its ability to modulate lipid metabolism in Chinese hamster ovary (CHO) cells deficient in Niemann-Pick Type C1 (Npc1), a model of Niemann-Pick disease Type C. Npc1-deficient CHO cells exhibited abnormal accumulation of unesterified cholesterol (UEC) and decreased levels of esterified cholesterol (EC) and long-chain fatty acids (LCFAs). Treatment with Mal-βCD significantly corrected these imbalances, indicating its efficacy in promoting intracellular lipid trafficking and esterification.
To elucidate the mechanistic basis, lysosomes isolated from Npc1-deficient cells were exposed to Mal-βCD, reproducing the in-cell effects. Furthermore, stable isotope tracer experiments using D4-labeled palmitic acid (D4-PA) revealed that Mal-βCD enhanced the biosynthesis of D4-LCFAs and D4-ECs. In a dual-labeling setup, simultaneous addition of D6-labeled UEC and D4-PA led to the synthesis of D6/D4-ECs, including conjugates of D6-UEC with D4-palmitic, stearic, or myristic acid, dependent on Mal-βCD treatment.