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H125

Sigma-Aldrich

(2-Hydroxypropyl)-γ-cyclodextrin

solid

Synonym(s):

HGC

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About This Item

CAS Number:
128446-34-4
UNSPSC Code:
12352201
NACRES:
NA.77

form

solid

concentration

1.000 mg/mL±0.005

technique(s)

cell culture | mammalian: suitable

color

white

solubility

H2O: 450 mg/mL

shipped in

ambient

storage temp.

room temp

SMILES string

O1[C@@H]2O[C@H]([C@H](O[C@@H]3O[C@H]([C@H](O[C@@H]4O[C@H]([C@H](O[C@@H]5O[C@H]([C@H](O[C@@H]6O[C@H]([C@H](O[C@@H]7O[C@H]([C@H](O[C@@H]8O[C@H]([C@H]1[C@H]([C@@H]8O)O)COCC(O)C)[C@H]([C@@H]7O)O)CO)[C@H]([C@@H]6O)O)COCC(O)C)[C@H]([C@@H]5O)O)CO)[C@H]([C@@H]4O)

InChI

1S/C51H88O38/c1-14(56)8-73-11-21-42-29(64)36(71)50(81-21)85-40-19(6-54)79-48(34(69)27(40)62)89-44-23(13-75-10-16(3)58)82-51(37(72)30(44)65)86-41-20(7-55)78-47(33(68)26(41)61)88-43-22(12-74-9-15(2)57)80-49(35(70)28(43)63)84-39-18(5-53)76-45(31(66)24(39)59)83-38-17(4-52)77-46(87-42)32(67)25(38)60/h14-72H,4-13H2,1-3H3/t14?,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-/m0/s1

InChI key

ODLHGICHYURWBS-RYJYQAAZSA-N

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Application

(2-Hydroxypropyl)-γ-cyclodextrin has been used to study its inhibitory effect on complement products and the inflammation induced by cholesterol crystals (CCs) from plasma samples.

Biochem/physiol Actions

(2-Hydroxypropyl)-γ-cyclodextrin (HPγCD) is a water-soluble alkylated cyclodextrin derivative. It has pharmaceutical potential as it may aid in enhancing the solubility of drugs for oral dosage preparations or formulations. It solubilizes macromolecules, such as cholesterol. It is like β cyclodextrin but solubilizes larger molecules. It favors lysosomes distribution across the cytoplasm and can modulate lysosomal dynamics and participates in lysosomal homeostasis. In the Niemann pick disease model, HPγCD reduces cholesterol accumulation.

Other Notes

Non-toxic solubilizer. γ-Cyclodextrin (8-glucose units) has a slightly larger cavity and can accommodate larger substrates than β-cyclodextrin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF5440
BCCD7945
BCCC1988
BCCB0627
BCBW1704

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Role of cyclodextrins in improving oral drug delivery
Loftsson T, et al.
The American Journal of Drug and Alcohol Abuse, 261-275 (2004)
Ashutosh Singhal et al.
Scientific reports, 10(1), 8663-8663 (2020-05-28)
Niemann-Pick type C (NPC) disease is a fatal neurodegenerative disorder caused by mutations in NPC1 and NPC2 genes that result in an accumulation of cholesterol in lysosomes. The majority of children with NPC die in adolescence. Currently, no FDA-approved therapies
Catherine R Barker et al.
International journal of cancer, 118(11), 2685-2693 (2005-12-31)
The modulation of DNA topology by topoisomerase II plays a crucial role during chromosome condensation and segregation in mitosis and has thus become a highly attractive target for chemotherapeutic drugs. However, these drugs are highly toxic, and so new approaches
Daria Cosaceanu et al.
Cancer letters, 222(2), 173-181 (2005-05-03)
Targeted disruption of the insulin-like growth factor 1 receptor (IGF-1R) restricts proliferation of tumor cells and enhances their in vitro radiosensitivity. However, there is little information regarding the effect of IGF-1R expression and function on the lung cancer response to
Complexation Thermodynamics of Cyclodextrins.
Mikhail V. Rekharsky et al.
Chemical reviews, 98(5), 1875-1918 (2002-02-19)
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Articles

Cyclodextrins

Many metabolically important compounds, such as lipid-soluble vitamins and hormones, have very low solubilities in aqueous solutions. Various techniques have been used to solubilize these compounds in tissue culture, cell culture, or other water-based applications.

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