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6-O-α-Maltosyl-β-cyclodextrin

Cat No.:V34054 Purity: ≥98%
6-O-α-Maltosyl-β-cyclodextrin is a novel and potent cellular cholesterol modifierthat can form soluble inclusion complex with cholesterol and is much less cytotoxic to human erythrocytes and Caco-2 cells.
6-O-α-Maltosyl-β-cyclodextrin
6-O-α-Maltosyl-β-cyclodextrin Chemical Structure CAS No.: 104723-60-6
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1g
5g
10g
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Product Description
6-O-α-Maltosyl-β-cyclodextrin is a novel and potent cellular cholesterol modifier that can form soluble inclusion complex with cholesterol and is much less cytotoxic to human erythrocytes and Caco-2 cells.
6-O-α-Maltosyl-β-cyclodextrin (CAS# 104723-60-6) is a derivative of beta-cyclodextrin, a cyclic oligosaccharide composed of seven glucose units linked by alpha-1,4-glycosidic bonds. It is a novel and potent cellular cholesterol modifier that can form soluble inclusion complexes with cholesterol. This property makes it useful in various applications related to cholesterol metabolism and cellular cholesterol modulation.
Biological Activity I Assay Protocols (From Reference)
Targets
6-O-α-Maltosyl-β-cyclodextrin targets cholesterol molecules within cellular membranes. By forming soluble inclusion complexes with cholesterol, it effectively extracts cholesterol from cell membranes. This action modulates cellular cholesterol levels, which can influence membrane fluidity, signaling pathways, and lipid metabolism. The compound does not target a specific protein receptor but acts through direct physicochemical interaction with cholesterol.
ln Vitro
Cellular cholesterol is eliminated by Mal-β-CD from inclusion complexes, and cholesterol/Mal-β-CD inclusion complexes (CLM) can be added to compensate for Mal-β-CD-induced cellular cholesterol deficit without causing cytotoxicity [1].
In vitro, 6-O-α-Maltosyl-β-cyclodextrin demonstrates potent cholesterol-modifying activity. It can form soluble inclusion complexes with cholesterol. The compound is much less cytotoxic to human erythrocytes and Caco-2 cells compared to other cholesterol modifiers. This favorable toxicity profile makes it suitable for cell culture applications where cholesterol modulation is required.
ln Vivo
In vivo, 6-O-α-Maltosyl-β-cyclodextrin has been used to modulate cholesterol levels in animal models. Its ability to extract cholesterol from tissues suggests potential applications in treating cholesterol-related disorders. However, detailed in vivo studies are limited. The compound's safety profile in animals appears favorable based on its low cytotoxicity in vitro.
Enzyme Assay
For in vitro binding assays, 6-O-α-Maltosyl-β-cyclodextrin can be evaluated for its ability to form inclusion complexes with cholesterol. The compound is incubated with cholesterol in aqueous solution, and complex formation is assessed by measuring cholesterol solubility or using techniques such as isothermal titration calorimetry or nuclear magnetic resonance spectroscopy. The binding affinity and stoichiometry can be determined from these experiments.
Cell Assay
For in vitro cell-based assays, 6-O-α-Maltosyl-β-cyclodextrin is typically tested on human erythrocytes or Caco-2 cells. Cells are treated with the compound at various concentrations (typically 0.1-10 mM) for 1-24 hours. Cholesterol extraction from cell membranes is measured using enzymatic cholesterol assays or by analyzing membrane cholesterol content. Cell viability is assessed using LDH release or MTT assays to evaluate cytotoxicity.
Animal Protocol
For in vivo animal experiments, 6-O-α-Maltosyl-β-cyclodextrin can be administered orally or intraperitoneally to rodents. Blood samples are collected to measure serum cholesterol levels. Tissue cholesterol content can be analyzed in liver, adipose tissue, and other organs. The compound's effect on cholesterol metabolism and its safety profile can be evaluated through histopathological examination of tissues.
ADME/Pharmacokinetics
Pharmacokinetic data for 6-O-α-Maltosyl-β-cyclodextrin are limited. As a large oligosaccharide with a molecular weight of 1459.27 g/mol and formula C₅₄H₉₀O₄₅, it is expected to have poor oral bioavailability due to its size and hydrophilicity. The compound is likely metabolized by gut microbiota or hydrolyzed by digestive enzymes. Standard pharmacokinetic studies would be required to determine its absorption, distribution, metabolism, and excretion profile.
Toxicity/Toxicokinetics
Toxicological data for 6-O-α-Maltosyl-β-cyclodextrin indicate that it is much less cytotoxic to human erythrocytes and Caco-2 cells compared to other cholesterol modifiers. This suggests a favorable safety profile for in vitro applications. However, comprehensive toxicological studies have not been extensively reported. The compound is classified as a research-grade reagent and is not for human therapeutic use.
References

[1]. 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. Carbohydr Res. 2012 Aug 1;357:68-74.

Additional Infomation
6-O-α-Maltosyl-β-cyclodextrin is a research-use only compound and has not been approved for clinical applications. It is also known as 6-O-alpha-D-maltosyl-beta-cyclodextrin. Its molecular weight is 1459.27, and its formula is C₅₄H₉₀O₄₅. The compound is used as an additive to improve the solubility of drugs such as quetiapine. It is available from various research chemical suppliers for cholesterol metabolism research.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C54H90O45
Molecular Weight
1459.2654
Exact Mass
1458.475
CAS #
104723-60-6
PubChem CID
78357834
Appearance
White to off-white solid powder
Density
1.9±0.1 g/cm3
Index of Refraction
1.719
LogP
-9.19
Hydrogen Bond Donor Count
27
Hydrogen Bond Acceptor Count
45
Rotatable Bond Count
13
Heavy Atom Count
99
Complexity
2480
Defined Atom Stereocenter Count
44
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
InChi Key
QFSFPJHBIGWPMD-PBVGKYIBSA-N
InChi Code
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
Chemical 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
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 100 mg/mL (~68.53 mM)
H2O : ≥ 60.5 mg/mL (~41.46 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (1.71 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (1.71 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (1.71 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 100 mg/mL (68.53 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 0.6853 mL 3.4264 mL 6.8527 mL
5 mM 0.1371 mL 0.6853 mL 1.3705 mL
10 mM 0.0685 mL 0.3426 mL 0.6853 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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