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  3. 6A-Azido-6A-deoxy-β-cyclodextrin

6A-Azido-6A-deoxy-β-cyclodextrin  (Synonyms: β-CDN3; 6A-deoxy-6A-azido-β-cyclodextrin)

Cat. No.: HY-101532 Purity: 98.0%
Handling Instructions Technical Support

6A-Azido-6A-deoxy-β-cyclodextrin (β-CDN3) is a site-specifically modified β-cyclodextrin with a single azido group replacing the hydroxyl group at the C6 position. 6A-Azido-6A-deoxy-β-cyclodextrin forms a host-guest inclusion complex with Dexamethasone (HY-14648), localizing the drug within its hydrophobic cavity, which restricts the rotational mobility of the drug and places Dexamethasone in a less polar environment. 6A-Azido-6A-deoxy-β-cyclodextrin acts as a coupling agent to graft β-cyclodextrin onto thermosensitive nanogels via strain-promoted alkyne-azide cycloaddition (SPAAC). 6A-Azido-6A-deoxy-β-cyclodextrin also serves as a click chemistry reagent. It contains an azide group and undergoes copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules bearing an alkyne group. It also undergoes strain-driven alkyne-azide cycloaddition (SPAAC) with molecules containing DBCO or BCN groups.

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6A-Azido-6A-deoxy-β-cyclodextrin

6A-Azido-6A-deoxy-β-cyclodextrin Chemical Structure

CAS No. : 98169-85-8

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Solid + Solvent (Highly Recommended)
10 mM * 1 mL in DMSO
ready for reconstitution
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Based on 1 publication(s) in Google Scholar

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Description

6A-Azido-6A-deoxy-β-cyclodextrin (β-CDN3) is a site-specifically modified β-cyclodextrin with a single azido group replacing the hydroxyl group at the C6 position. 6A-Azido-6A-deoxy-β-cyclodextrin forms a host-guest inclusion complex with Dexamethasone (HY-14648), localizing the drug within its hydrophobic cavity, which restricts the rotational mobility of the drug and places Dexamethasone in a less polar environment. 6A-Azido-6A-deoxy-β-cyclodextrin acts as a coupling agent to graft β-cyclodextrin onto thermosensitive nanogels via strain-promoted alkyne-azide cycloaddition (SPAAC). 6A-Azido-6A-deoxy-β-cyclodextrin also serves as a click chemistry reagent. It contains an azide group and undergoes copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules bearing an alkyne group. It also undergoes strain-driven alkyne-azide cycloaddition (SPAAC) with molecules containing DBCO or BCN groups[1][2].

In Vitro

6A-Azido-6A-deoxy-β-cyclodextrin is isolated as a stable intermediate following nucleophilic substitution of 6A-monotosyl-β-cyclodextrin with sodium azide at 80 °C in DMF[1].
6A-Azido-6A-deoxy-β-cyclodextrin (0.54-1.6 µmol; overnight, room temperature) conjugates to dPG-BCN via SPAAC at room temperature to form dPG-βCD conjugates with 1% and 3% βCD functionalization, which exhibit reduced water solubility with higher βCD content[2].
6A-Azido-6A-deoxy-β-cyclodextrin (34 µmol; 1 h, 45 °C) successfully grafts to the surface of thermoresponsive nanogels via SPAAC post-functionalization, forming stable spherical particles with minor reduction in thermoresponsive cloud point temperature and confirmed βCD presence via ANS fluorescence[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

1160.00

Formula

C42H69N3O34

CAS No.
Appearance

Solid

Color

White to off-white

SMILES

[N-]=[N+]=NC[C@@H](O[C@@](O[C@]([C@@H]1O)([H])[C@H](O[C@@](O[C@]([C@@H]2O)([H])[C@H](O[C@@](O[C@]([C@@H]([C@H]3O)O)([H])[C@H]4CO)([H])[C@@H]2O)CO)([H])[C@@H]1O)CO)([H])[C@H](O)[C@H]5O)[C@@]5([H])O[C@@]([C@@H]([C@@H](O)[C@]6([H])O[C@@]([C@@H]([C@@H](O)[C@]7([H])O[C@@]([C@@H]([C@@H](O)[C@]8([H])O[C@@]3([H])O4)O)([H])O[C@@H]8CO)O)([H])O[C@@H]7CO)O)([H])O[C@@H]6CO

Shipping

Room temperature in continental US; may vary elsewhere.

Storage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
In Vitro: 

DMSO : 125 mg/mL (107.76 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 0.8621 mL 4.3103 mL 8.6207 mL
5 mM 0.1724 mL 0.8621 mL 1.7241 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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Purity & Documentation
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 0.8621 mL 4.3103 mL 8.6207 mL 21.5517 mL
5 mM 0.1724 mL 0.8621 mL 1.7241 mL 4.3103 mL
10 mM 0.0862 mL 0.4310 mL 0.8621 mL 2.1552 mL
15 mM 0.0575 mL 0.2874 mL 0.5747 mL 1.4368 mL
20 mM 0.0431 mL 0.2155 mL 0.4310 mL 1.0776 mL
25 mM 0.0345 mL 0.1724 mL 0.3448 mL 0.8621 mL
30 mM 0.0287 mL 0.1437 mL 0.2874 mL 0.7184 mL
40 mM 0.0216 mL 0.1078 mL 0.2155 mL 0.5388 mL
50 mM 0.0172 mL 0.0862 mL 0.1724 mL 0.4310 mL
60 mM 0.0144 mL 0.0718 mL 0.1437 mL 0.3592 mL
80 mM 0.0108 mL 0.0539 mL 0.1078 mL 0.2694 mL
100 mM 0.0086 mL 0.0431 mL 0.0862 mL 0.2155 mL
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Product Name:
6A-Azido-6A-deoxy-β-cyclodextrin
Cat. No.:
HY-101532
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