- Application of host-guest chemistry in nanotube-based device fabrication: Photochemically controlled immobilization of azobenzene nanotubes on patterned α-CD monolayer/Au substrates via molecular recognition
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Azobenzene-functionalized nanotubes recognized and attached onto well-defined complementary regions of thiolated α-CD SAM/Au substrates via host-guest molecular recognition. The binding between the azobenzene nanotubes and the α-CD SAM/Au substrates was c
- Banerjee, Ipsita A.,Yu, Lingtao,Matsui, Hiroshi
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- Synthesis and biological evaluation of novel pentacyclic triterpene α-cyclodextrin conjugates as HCV entry inhibitors
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Hepatitis C virus (HCV) entry is a key target for the treatment of chronic HCV infection. In our continuing efforts to identify novel potential anti-HCV entry inhibitors, a series of water-soluble triazole-bridged α-cyclodextrin-pentacyclic triterpene conjugates were easily synthesized with moderate to good yields. These novel compounds were fully identified and characterized by 1D and 2D NMR spectroscopy and ESI-HRMS. The anti-HCV entry activities were determined based on HCVpp/VSVGpp entry assays. The best results were found for compounds 15 and 18, which displayed the most promising anti-HCV entry activities with average IC50values of 1.18?μM and 0.25?μM, respectively. In addition, the in?vitro cytotoxicity activity of the two compounds against MDCK cells showed no toxicity at 100?μM. Five different binding assays were set up to identify the action mechanism. The results showed that the compounds exert their inhibitory activity at the post-binding step and subsequently prevent virus entry.
- Xiao, Sulong,Wang, Qi,Si, Longlong,Zhou, Xiaoshu,Zhang, Yongmin,Zhang, Lihe,Zhou, Demin
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- CONVENIENT PREPARATION AND EFFECTIVE SEPARATION OF THE C-2 AND C-3 TOSYLATES OF α-CYCLODEXTRIN
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Secondary tosylates of α-cyclodextrin were conveniently prepared by the reaction of the cyclodextrin with tosyl chloride in alkaline water where pH of the mixture should be allowed to decrease as the proceeding of reaction, and were effectivelly separated by reversed-phase column chromatography.
- Fujita, Kahee,Nagamura, Satoru,Imoto, Taiji
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- Unraveling unidirectional threading of α-cyclodextrin in a [2]rotaxane through spin labeling approach
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We present here the results of a CW-ESR investigation of a double spin labeled α-cyclodextrin-based [2]rotaxane that is characterized by the presence of nitroxide labels both at the wheel and at the dumbbell. This was accomplished by synthesizing a spin l
- Casati, Costanza,Franchi, Paola,Pievo, Roberta,Mezzina, Elisabetta,Lucarini, Marco
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- MONOTOSYLATED α-AND β-CYCLODEXTRINS PREPARED IN AN ALKALINE AQUEOUS SOLUTION
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In order to establish the tosylated positions of α- and β-cyclodextrins, 13C-nmr spectra for the monotosyl-derivatives prepared in an alkaline aqueous solution were examined and determined to be in the 6-position of one glucose unit for β-cyclodextrin and
- Takahashi, Keiko,Hattori, Kenjiro,Toda, Fujio
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- Synthesis and biological evaluation of multivalent carbohydrate ligands obtained by click assembly of pseudo-rotaxanes
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Multivalent carbohydrate ligands have been prepared by assembling α-cyclodextrin-based pseudo-rotaxanes through "click chemistry". The inclusion complex formed by a lactosyl-α-CD conjugate and a decane axle carrying a lactosyl stopper at one extremity and
- Chwalek, Martin,Auzely, Rachel,Fort, Sebastien
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- ANTI-MSR1 ANTIBODIES AND METHODS OF USE THEREOF
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Provided herein are antibodies and antigen-binding fragments that bind MSR1 and methods of use thereof. According to certain embodiments, the antibodies bind human MSR1 with high affinity. In certain embodiments, the antibodies bind MSR1 without blocking, or blocking less than 90%, of modified LDL binding to MSR1. In some embodiments, the antibodies bind cell surface expressed-MSR1 and are internalized. The antibodies of the invention may be fully human antibodies. The invention includes anti-MSR1 antibodies, or antigen-binding fragments thereof, conjugated to drugs or therapeutic compounds.
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Paragraph 0545
(2019/11/28)
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- CYCLODEXTRIN PROTEIN DRUG CONJUGATES
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Provided herein are compounds, compositions, conjugates and methods for the treatment of diseases, and/or conditions such as, but not limited to, proliferative diseases. In certain embodiments, compounds, compositions, and conjugates are provided, which include cyclodextrin-based linker-payloads and protein conjugates thereof, and/or in combination with other agents. By administering these compounds, compositions, and conjugates as described herein to specific target cells, side-effects due to non-specific binding phenomena, for example, to non-target cells are reduced.
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Paragraph 0364
(2018/12/04)
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- A manganese porphyrin-α-cyclodextrin conjugate as an artificial enzyme for the catalytic epoxidation of polybutadiene
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We describe a manganese porphyrin-α-cyclodextrin conjugate as a catalyst for the epoxidation of cis-polybutadiene with trans-epoxide preference, which is a reverse stereoselectivity as compared to normal porphyrin catalysts. A clamp-like mechanism is prop
- Zhang, Qi-Wei,Elemans, Johannes A. A. W.,White, Paul B.,Nolte, Roeland J. M.
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supporting information
p. 5586 - 5589
(2018/06/04)
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- Enhanced single-isomer separation and pseudoenantiomer resolution of new primary rim heterobifunctionalized α-cyclodextrin derivatives
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The synthesis of batch-to-batch reproducible cyclodextrin (CD) derivatives often requires functionalization at specific positions of the CD skeleton. However, the regioselective preparation of this type of CD derivatives remains a challenge in synthetic c
- Tichá, Iveta,Benkovics, Gábor,Malanga, Milo,Jind?ich, Jind?ich
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supporting information
p. 2829 - 2837
(2018/11/27)
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- SELF-ASSEMBLED TARGETED INCLUSION COMPLEXES FOR DRUG DELIVERY
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Inclusion complexes are provided containing a targeted carrier non-covalently associated with an active agent. The targeted carrier includes an inclusion host that binds the active agent or a binding partner attached to the active agent. The targeted carrier includes a targeting moiety attached to the inclusion host or to a polymer or linker attached thereto. Pharmaceutical formulations of the inclusion complexes are provided. Methods of making the inclusion complexes and formulations thereof are provided. Methods of using the inclusion complexes and formulations are provided. In some embodiments the inclusion complex includes a progesterone or estrogen targeting moiety that targets the inclusion complex to cancer cells. The targeting can cause internalization of the active agent in the target cells. In some embodiments the active agent is an anthracycline such as doxorubicin and the target cells are cancer cells.
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Page/Page column 29
(2016/09/22)
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- Conductive Elastomers with Autonomic Self-Healing Properties
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Healable, electrically conductive materials are highly desirable and valuable for the development of various modern electronics. But the preparation of a material combining good mechanical elasticity, functional properties, and intrinsic self-healing ability remains a great challenge. Here, we design composites by connecting a polymer network and single-walled carbon nanotubes (SWCNTs) through host-guest interactions. The resulting materials show bulk electrical conductivity, proximity sensitivity, humidity sensitivity and are able to self-heal without external stimulus under ambient conditions rapidly. Furthermore, they also possess elasticity comparable to commercial rubbers.
- Guo, Kun,Zhang, Da-Li,Zhang, Xiao-Mei,Zhang, Jian,Ding, Li-Sheng,Li, Bang-Jing,Zhang, Sheng
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supporting information
p. 12127 - 12133
(2015/10/12)
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- A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges
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An efficient synthetic route toward the preparation of a complete series of monosubstituted tetraalkylammonium cyclodextrin (CD) derivatives is presented. Monotosylation of native CDs (α-, β-, γ-) at position 6 gave the starting material. Reaction of monotosylate (mono-Ts-CD) with 45% aqueous trimethylamine gave CDs substituted with one cationic functional group in a single step. Derivatives equipped with a substituent containing two cationic sites separated by an ethylene or a propylene linker were prepared by reacting mono-Ts-CD with neat N,N,N'-trimethylethane-1,2-diamine or N,N,N'- trimethylpropane-1,3-diamine and subsequent methylation by CH3I in good yields. Finally, analogues bearing a moiety with three tetraalkylammonium sites were synthesized by reacting mono-Ts-CD with bis(3-aminopropyl)amine and subsequent methylation. The majority of the presented reactions are very straightforward with a simple work-up, which avoids the need of chromatographic separation. Thus, these reactions are suitable for the multigram-scale production of monosubstituted cationic CDs. 2014 Popr et al;.
- Popr, Martin,Hybelbauerova, Simona,Jindrich, Jindrich
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supporting information
p. 1390 - 1396
(2014/07/22)
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- The Synthesis of a Multiblock Osteotropic Polyrotaxane by Copper(I)-Catalyzed Huisgen 1,3-Dipolar Cycloaddition
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The design and synthesis of a novel bone-targeting polyrotaxane delivery system that utilizes alendronate (ALN) as targeting moiety is presented in this manuscript. For the introduction of ALN, it is first conjugated to α-cyclodextrin (α-CD) and subsequen
- Hein, Christopher D.,Liu, Xin-Ming,Chen, Fu,Cullen, Diane M.,Wang, Dong
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scheme or table
p. 1544 - 1556
(2011/10/05)
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- 6A-O-[(4-biphenylyl)acetyl]-alpha-, -beta-, and -gamma-cyclodextrins and 6A-deoxy-6A-[[(4-biphenylyl)acetyl]amino]-alpha-, -beta-, and -gamma-cyclodextrins: potential prodrugs for colon-specific delivery.
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Cyclodextrins (CyDs) are known to be fermented to small saccharides by colonic microflora, whereas they are only slightly hydrolyzable and thus are not easily absorbed in the stomach and small intestine. This property of CyDs is particularly useful for colon-specific delivery of drugs. In this study, an antiinflammatory 4-biphenylylacetic acid (BPAA) was selectively conjugated onto one of the primary hydroxyl groups of alpha-, beta-, and gamma-CyDs through an ester or amide linkage, 6A-O-[(4-biphenylyl)acetyl[-alpha-, -beta-, and -gamma-CyDs (1-3) and 6A-deoxy-6A-[[(4-biphenylyl)acetyl]amino]-alpha-, -beta-, and -gamma-CyDs (4-6). In rat cecal and colonic contents (10%, w/v), 1 and 3 released more than 95% of BPAA within 1-2 h, and 2 released about 50% of the drug within 12 h. The amide prodrugs, 4-6, did not release BPAA in the cecal contents, but gave BPAA/maltose or BPAA/triose conjugates linked through an amide bond. On the other hand, these prodrugs were found to be stable in the contents of rat stomachs and small intestines, in intestinal or liver homogenates, and in rat blood. The serum levels of BPAA increased about 3 h after oral administration of 1 and 3 to rats, accompanying a marked increase in the serum levels, whereas 2 and 4-6 resulted in little increase of the serum levels. These facts suggest that BPAA is released after the ring opening of CyDs followed by the ester hydrolysis, and the BPAA activation takes place site-specifically in the cecum and colon. Therefore, the present CyD prodrug approach provides a versatile means of constructing a novel colon-specific drug delivery system.
- Uekama,Minami,Hirayama
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p. 2755 - 2761
(2007/10/03)
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- Synthesis and Properties of 6A-Amino-6A-deoxy-α- and -β-cyclodextrin
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The monotosylates obtained by treatment of α- and β-cyclodextrin with p-methylbenzenesulfonyl chloride reacted with ammonia to give the title compounds. These amines are of unusually low basicity, with pKa values of 8.70 and 8.72, respectively. In water at 25 deg, the hydrochloride salt of the amine derived from β-cyclodextrin is approximately 40 times more soluble than β-cyclodextrin and, through complexation, the salt increases the solubility of Nabumetone over 800 times.
- Brown, Susan E.,Coates, John H.,Coghlan, Daniel R.,Easton, Christopher J.,Eyk, Stephen J. van,et al.
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p. 953 - 958
(2007/10/02)
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- Fluorescent sensors of molecular recognition. Modified cyclodextrins capable of exhibiting guest-responsive twisted intramolecular charge transfer fluorescence
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α-, β-, and γ-cyclodextrin derivatives bearing a p-(dimethylamino)benzoyl (DMAB) moiety (DMAB-αCyD, DMAB-βCyD, and DMAB-γCyD, respectively) have been synthesized as fluorescent sensors of molecular recognition. These compounds show dual fluorescence emission arising from normal planar (NP) and twisted intramolecular charge transfer (TICT) exited states, and among them strong TICT emission was observed for DMAB-βCyD. The induced circular dichroism spectra of the derivatives suggest that only DMAB-βCyD among other derivatives binds the DMAB moiety into its own cavity, forming an intramolecular inclusion complex. This conformation was confirmed by the analysis of its 1H-NMR data and was related to its strong TICT emission. The intensity of the TICT emission of DMAB-βCyD decreased markedly with increasing the concentration of cyclic alchols, monoterpenes, or steroids. This observation was explained by the guest-induced location change of the DMAB moiety from inside to outside of the cavity. Since the TICT emission intensity depended on the size, shape, and polarity of the guest molecules, DMAB-βCyD was useful as a fluorescent chemosensor of molecular recognition.
- Hamasaki, Keita,Ikeda, Hiroshi,Nakamura, Asao,Ueno, Akihiko,Toda, Fujio,Suzuki, Iwao,Osa, Tetsuo
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p. 5035 - 5040
(2007/10/02)
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