Inhibitory Effect of Sulfobutyl Ether β‐cyclodextrin on DY‐9760e‐Induced Cellular Damage: In vitro and in vivo Studies

Nagase, Yukihiko; Arima, Hisatomi; Wada, Koh; Sugawara, Takafumi; Satoh, Hiroshi; Hirayama, Fumitoshi; Uekama, Kaneto

doi:10.1002/jps.10517

Cited by 17 publications

(10 citation statements)

References 16 publications

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“…[17][18][19][20] Among these compounds, hydrophilic CyDs such as HP-b-CyD, SBE-b-CyD, and branched b-CyD have received special attention, because their toxicity is very low and aqueous solubility is very high, promising a parenteral use. [63][64][65][66][67][68] The glucuronyl-glucosyl-b-CyD (GUG-b-CyD) is a new entry of branched CyDs, which contains a carboxyl group in the branched maltosyl residue. 69) In fact, the hemolytic activity of GUG-b-CyD on rabbit erythrocytes is lower than that of b-CyD and G2-b-CyD (see Fig.…”

Section: Some Characteristics Of Cyd Derivatives As Drug Carriersmentioning

confidence: 99%

Design and Evaluation of Cyclodextrin-Based Drug Formulation

2004

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Section: Some Characteristics Of Cyd Derivatives As Drug Carriersmentioning

confidence: 99%

Design and Evaluation of Cyclodextrin-Based Drug Formulation

2004

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“…Although the dimensional fit between host cavity and guest molecule is important in the formation of the complex, hydrophobic desolvation, hydrogen bonding, and van der Waals interactions are among the most important driving forces for CD complexation [1,4]. Stable inclusion complexes of various drugs with SBE-␤-CDs that have 4 to 7 average degrees of substitution of SBE have been reported [5][6][7]. One way to evaluate the stability of the inclusion complex is to measure their association constants [4,7].…”

mentioning

confidence: 98%

“…Stable inclusion complexes of various drugs with SBE-␤-CDs that have 4 to 7 average degrees of substitution of SBE have been reported [5][6][7]. One way to evaluate the stability of the inclusion complex is to measure their association constants [4,7].…”

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Capillary electrophoretic separation and theoretical study of inclusion complexes of sulfobutyl ether β‐cyclodextrin with estrogens

Deng

Huang

2004

Int J of Quantum Chemistry

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ABSTRACT:Five estrogens (2-hydroxyestrone, 2-methoxyestradiol, estrone, estriol, and 17␣-estradiol) and two stereoisomers (17␣-and 17␤-estradiol) have been successfully separated using capillary electrophoresis with anionic sulfobutyl ether ␤-cyclodextrin (SBE-␤-CD). The SBE-␤-CD used in the separation was a mixture of positional and regional isomers containing from 1 to 10 sulfobutyl ether groups with an average degree of substitution of four per cyclodextrin; thus, a tetra-SBE substituted CD, SBE[4]-␤-CD, has been chosen as the model host molecule in the present study. Relative to the position of the cavity, three initial arrangements of the 4 SBE groups, 0-, 2-, and 4-up, have been considered. In addition two types of inclusion complexes, cis and trans orientations, are also considered for each estrogen. In the cis structure the SBE group of the cyclodextrin and the phenol group of the estrogen are on the same side, while in the trans structure the two groups are on opposite sides. The objective of the present study is to perform PM3 (Parametric Method 3) semiempirical molecular orbital calculations on these six inclusion complexes (12 different orientations) for each SBE[4]-␤-CD to correlate the migration order with their relative stability. Theoretical calculations have shown that only when SBE groups are perpendicular to the axis of CD (0-up arrangement), the cavity is open on both sides for incoming guest molecules. A correlation was observed between the total heats of formation for the cis and trans estrogen-CD inclusion complexes of the same estrogen and the electrophoretic migration time although the relationship is not linear, suggesting that both orientations may occur simultaneously. In other two SBE[4]-␤-CDs, the narrower side of the cavity is partially capped due to the formation of intra-hydrogen bonds among three of the four SBE groups. Thus, a guest molecule can enter the cavity from the wide end of the cavity only. As a result, the estrogen molecules protrude from the cavity in most cases.

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“…Compared to neutral HP-β-CD, the electronegative SBE7-β-CD formed more stable inclusion complex with 134, and resulted in the significant enhancement of water solubility and light stability for drug 134 [248] , and also decreased the DY-9760e-induced cytotoxicity toward HUVECs and vascular damage in rabbits [249] . …”

Section: Supermolecules As Cardiovascular Agentsmentioning

confidence: 99%

Review on supermolecules as chemical drugs

Zhou

Gan

Zhang

et al. 2009

Sci. China Ser. B-Chem.

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Supramolecular medicinal chemistry field has been a quite rapidly developing, increasingly active and newly rising interdiscipline which is the new expansion of supramolecular chemistry in pharmaceutical sciences, and is gradually becoming a relatively independent scientific area. Supramolecular drugs could be defined as medicinal supermolecules formed by two or more molecules through noncovalent bonds. So far a lot of supermolecules as chemical drugs have been widely used in clinics. Supermolecules as chemical drugs, i.e. supramolecular chemical drugs or supramolecular drugs, which might have the excellences of lower cost, shorter period, higher potential as clinical drugs for their successful research and development, may possess higher bioavailability, better biocompatibility and drug-targeting, fewer multidrug-resistances, lower toxicity, less adverse effect, and better curative effects as well as safety, and therefore exhibit wide potential application. These overwhelming advantages have drawn enormous special attention. This paper gives the definition of supramolecular drugs, proposes the concept of supramolecular chemical drugs, and systematically reviews the recent advances in the research and development of supermolecules, including organic and inorganic complex ones as chemical drugs in the area of antitumor, anti-inflammatory, analgesic, antimalarial, antibacterial, antifungal, antivirus, anti-epileptic, cardiovascular agents and magnetic resonance imaging agents and so on. The perspectives of the foreseeable future and potential application of supramolecules as chemical drugs are also presented.

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Inhibitory Effect of Sulfobutyl Ether β‐cyclodextrin on DY‐9760e‐Induced Cellular Damage: In vitro and in vivo Studies

Cited by 17 publications

References 16 publications

Design and Evaluation of Cyclodextrin-Based Drug Formulation

Design and Evaluation of Cyclodextrin-Based Drug Formulation

Capillary electrophoretic separation and theoretical study of inclusion complexes of sulfobutyl ether β‐cyclodextrin with estrogens

Review on supermolecules as chemical drugs

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