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Merck
모든 사진(4)

문서

C4555

Sigma-Aldrich

Methyl-β-cyclodextrin

powder, BioReagent, suitable for cell culture

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About This Item

CAS Number:
UNSPSC 코드:
12352201
NACRES:
NA.77

생물학적 소스

synthetic (organic)

무균

non-sterile

제품 라인

BioReagent

형태

powder

분자량

~1320 g/mol

라벨링 범위

1.5-2.1 methyl per mol glucose

기술

cell culture | mammalian: suitable

mp

180-182 °C (lit.)

solubility

H2O: 50 mg/mL

저장 온도

room temp

InChI

1S/C56H98O35/c1-64-15-22-36-29(57)43(71-8)50(78-22)86-37-23(16-65-2)80-52(45(73-10)30(37)58)88-39-25(18-67-4)82-54(47(75-12)32(39)60)90-41-27(20-69-6)84-56(49(77-14)34(41)62)91-42-28(21-70-7)83-55(48(76-13)35(42)63)89-40-26(19-68-5)81-53(46(74-11)33(40)61)87-38-24(17-66-3)79-51(85-36)44(72-9)31(38)59/h22-63H,15-21H2,1-14H3

InChI key

QGKBSGBYSPTPKJ-UHFFFAOYSA-N

유사한 제품을 찾으십니까? 방문 제품 비교 안내

일반 설명

Methyl-β-cyclodextrin is a heptasaccharide, soluble in water, and has more affinity to cholesterol due to the presence of hydrophobic core. Cyclodextrins are cyclic oligosaccharides consisting of 6, 7, or 8 glucopyranose units, usually referred to as α-, β-, or γ-cyclodextrins, respectively. These compounds have rigid doughnut-shaped structures making them natural complexing agents. The unique structures of these compounds owe their stability to intramolecular hydrogen bonding between the C2- and C3-hydroxyl groups of neighboring glucopyranose units. The molecule takes on the shape of a torus with the C2- and C3-hydroxyls located around the larger opening and the more reactive C6-hydroxyl aligned around the smaller opening. The arrangement of C6-hydroxyls opposite the hydrogen bonded C2- and C3-hydroxyls forces the oxygen bonds into close proximity within the cavity, leading to an electron rich, hydrophobic interior. The size of this hydrophobic cavity is a function of the number of glucopyranose units forming the cyclodextrin.

The solubility of natural cyclodextrins is very poor. In the late 1960′s, it was discovered that chemical substitutions at the 2, 3, and 6 hydroxyl sites would greatly increase solubility. Most chemically modified cyclodextrins are able to achieve a 50% (w/v) concentration in water.

애플리케이션

Methyl-β-cyclodextrin has been used:
  • to study the effect of cholesterol depletion, from sperm membrane on sperm′s ability to undergo acrosome reaction.
  • to determine the effect of caveolin overexpression and its loss on pro-survival and pro-growth signaling
  • in conventional in vitro fertilization

생화학적/생리학적 작용

Methyl-β-cyclodextrin (MβCD) is commonly applicable as an inhibitor and modifies cholesterol domains on the cellular surface. It causes depletion of cholesterol on the membrane. It is also known to prevent the action of cholera toxin, nitric oxide (NO) synthase and glucose transporter through internalization. This is observed in specific to lipid rafts and caveolae endocytosis. MβCD induces eflux as well as influx of cholesterol. It can affect cell viability as the genes regulating cholesterol levels are upregulated, due to decreased cholesterol level by the action of MβCD. It can be used to increase the solubility of non-polar substances such as fatty acids, lipids, vitamins and cholesterol for use in cell culture applications. Cavity size is the major determinant as to which cyclodextrin is used in complexation. The cavity diameter of β-cyclodextrins or β-glucopyranose unit compounds is well-suited for use with molecules the size of hormones, vitamins and many compounds frequently used in tissue and cell culture applications. For this reason, β-cyclodextrin is most commonly used as a complexing agent.

재구성

Solutions may be obtained by stirring 30 min at room temperature. Alternatively, sonication with cooling may be employed. Solutions may be stored for several months at 4°C. Solid should be stored tightly sealed at room temperature.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

368.6 °F

Flash Point (°C)

187 °C

개인 보호 장비

Eyeshields, Gloves, type N95 (US)


시험 성적서(COA)

제품의 로트/배치 번호를 입력하여 시험 성적서(COA)을 검색하십시오. 로트 및 배치 번호는 제품 라벨에 있는 ‘로트’ 또는 ‘배치’라는 용어 뒤에서 찾을 수 있습니다.

이 제품을 이미 가지고 계십니까?

문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문

Redox Cell Biology and Genetics, Part 2
Methods in Enzymology, 60(3), 187-193 (2002)
Microdroplet in vitro fertilization can reduce the number of spermatozoa necessary for fertilizing oocytes
Hasegawa A, et al.
Journal of Reproduction and Development, 60(3), 187-193 (2014)
Heng-Cong Luo et al.
International journal of nanomedicine, 12, 1085-1096 (2017-02-23)
Several biological barriers must be overcome to achieve efficient nonviral gene delivery. These barriers include target cell uptake, lysosomal degradation, and dissociation from the carrier. In this study, we compared the differences in the uptake mechanism of cationic, star-shaped polymer/MMP-9siRNA
Ecancermedicalscience, 60(3), 187-193 (2008)
Cholesterol addition protects membrane intactness during cryopreservation of stallion sperm
Oliveira CH de, et al.
Animal Reproduction Science, 118(2-4), 194-200 (2010)

문서

How palmitic acid, other fatty acids and other cell culture components affect the performance of serum-free, protein-free cell culture systems used for biomanufacturing heterologous proteins including monoclonal antibodies.

Cyclodextrin solubilizes fat-soluble vitamins and hormones, enhancing their solubility in water for cell culture applications.

How the unsaturated fatty acid, oleic acid and other cell culture components affect the performance of serum-free, protein-free cell culture systems used for biomanufacturing heterologous proteins including monoclonal antibodies.

Techniques for solubilizing metabolically important compounds in aqueous solutions are reviewed.

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