Controlled Drug Release from Cyclodextrin-Gated Mesoporous Silica

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Controlled Drug Release From Cyclodextrin-Gated Mesoporous Silica Nanoparticles Based on Switchable Host-Guest Interactions Shouhui Yi, Jiaoni Zheng, Pin Lv, Dongjing Zhang, Xiaoyuan Zheng, Ying Zhang, and Rongqiang Liao Bioconjugate Chem., Just Accepted Manuscript • DOI: 10.1021/acs.bioconjchem.8b00416 • Publication Date (Web): 03 Aug 2018 Downloaded from http://pubs.acs.org on August 4, 2018

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Bioconjugate Chemistry

Controlled Drug Release From Cyclodextrin-Gated Mesoporous Silica Nanoparticles Based on Switchable Host-Guest Interactions Shouhui Yi [a], Jiaoni Zheng [b], Pin Lv [c], Dongjing Zhang[d], Xiaoyuan Zheng [b], Ying Zhang [b], Rongqiang Liao *[b] [a] Oncology Center, The Second Affiliated Hospital of Chongqing Medical University, Chongqing, 400010, P.R. China. [b] Department of pharmacy, Chongqing Emergency Medical Center, Chongqing University Central Hospital, Chongqing, 400014, P.R. China. [c] Industrial Crop Research Institute, Yunnan Academy of Agricultural Sciences, Kunming, 650205, P.R. China [d] Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, 650500, P.R. China

These authors contributed equally to this article. * Corresponding author: E-mail: [email protected]

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Abstract: With the development of materials science and pharmaceutics, the application of mesoporous silica nanoparticles with gated switch in the field of drug delivery has attracted much attention in the past decades. Cyclodextrins (CD) as promising gated materials have become a new area of interest in recent years due to their properties of self-assembly and function of host-guest interaction. CD is one kind of extensively studied host molecules and the host-guest interactions with different guest molecules can respond to different signal, thus can be applied as intelligent gated switch for smart drug carriers. Switchable gatekeepers based on CD hosts with different guest molecules (such as benzimidazole, azobenzene, and ferrocene) respond to different stimuli modes (such as pH, light and redox) that change the host-guest interactions and trigger drug release. The different structural features, mechanisms of action, and potent applications of these switchable gatekeepers are discussed. In addition, some personal perspectives and challenge on this field are presented.

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1. Introduction Tumors are common diseases, generally speaking, they are among the leading causes of death worldwide, and their incidence and mortality are increasing as the population ages(1). However, traditional chemotherapy has great toxic and side effects. Thus, smart drug carriers are developed as alternatives because of their potentiality to selectively target tumor tissues while sparing normal tissues(2). As the development of modern nanomedicine, the application of mesoporous silica nanoparticles(MSNs) in the field of drug delivery has attracted much attention in the past decades (3). MSNs are of great interest and value because they show the characteristics of uniform pore and particle size distribution, unique porous structure in the nanometre range, and versatile functionalization(4-6). The particular morphology allows them to accommodate significant amounts of small molecules, especially chemotherapy drugs. Unique porous structure of MSNs can make them deliver different drugs because the diameter of the mesopores can be tuned to retain different chemotherapy drugs from two to five nanometers(7). In general, chemotherapy drugs present higher cytotoxicity to normal tissues. It is compulsory to design a strategy to avoid drugs premature release before reaching the cancer tissues(8). It is possible to control drug release via placing different macromolecules on the entrance of these pores of MSNs. These macromolecules mainly act as gatekeepers hampering the drug escape by steric hindrance effect(9). The main mechanism of action is that the attachments of these capping agents can be carried out in a reversible way to control drug release once the MSNs are at the cancer tissues. Host-guest inclusion can make two or more chemical moieties reversibly combined together in a facile way. Typically host-guest interactions include electrostatic interactions, hydrogen bonding interactions, π-π stacking interactions, hydrophobic interactions. The premise is, certainly, molecular shape or size matching(10, 11). Because of the weak binding force, host-guest interactions can be reversibly changed under the influence of external conditions(12). This kind of interactions are attracting more and more attention arising from the weak binding force in drug delivery systems. Reversible ACS Paragon Plus Environment


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gating switches can be designed to control drug release by host-guest interaction. For example, different environments conditions between tumor and normal tissues can be used to trigger to pen gating switch and then the drugs will be release.. Generally, host molecules

with

hydrophobic

cavities,

including

cyclodextrins,

calixarenes,

cucurbiturils and pillararenes, can encapsulate hydrophobic guest molecules into their cavities. Most importantly, host-guest interactions can respond to external stimulus signals, such as magnetic field, light, electricity, pH, redox, temperature and so on. Therefore, these host molecules can be used as gate switch for the smart drug carriers based on mesoporous silica drug carrier (13, 14). Cyclodextrins possess peculiar macrocyclic structure containing six, seven, or eight glucopyranose units, called α-, β- and γ-CD, respectively, which can interact with many hydrophobic guest molecules with suitable sizes, such as adamantine (AD), benzimidazole (BzI), azobenzene (Azo) and ferrocene (Fc) and so on(15, 16). CDs are considered as good choices for the gatekeeper based on MSNs, because of their facile chemical modification, good biocompatibility, and nontoxicity toward biological systems. The bulky CDs that encircles guest molecules can bind to the recognition site on the guest molecules via host-guest interactions(17). In such a situation, host-guest complex serves as the gatekeeper of the pore entrances. Moreover, the binding effect between the CDs and guest molecules is reversible. In other words, binding constant of host-guest complex can be reduced under external stimulus signals which cause automatical departure of guest molecules from the cavity of CDs. As a result, it leads to the unlocking of pore entrances. In the previous reviews, drug delivery systems based on MSNs have been summarized. These MSNs can load large amounts of drugs and once into the blood circulation preferentially accumulate in tumor tissue through the enhanced permeation and retention (EPR) effect. More importantly, these MSNs have shown good biocompatibility and no cytotoxicity. However, these drug delivery systems based on MSNs are intrinsically without stimuli responsive ability, so it controlled release can only

be

realized

by

introducing

other

segments,

including

inorganic

nanomaterials(18-22), polymers(23-27) and biomacromolecules(28-31). There are ACS Paragon Plus Environment

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many reviews regarding gatekeepers based on CDs without stimuli responsive ability, or those with controlled release behavior but based on other sensitive polymer skeletons(32-34). However, the construction and application of gatekeepers based on cyclodextrin and sensitive guest molecules have not been specific summarized. In this review, we will mainly focus on drug delivery systems based on CDs used as the stimuli responsive gatekeepers. As stated above, CDs can encapsulate various hydrophobic guest molecules in their cavity with high size- and shape- selectivity. If the hydrophilicity, size and shape of the guest molecules are changed by external stimulus signals, host-guest interaction will be weakened. This is the basic principle that gatekeepers based on the host-guest interactions can be controled. Different gatekeepers based on CDs with different guest molecules (such as BzI, Azo and Fc) can respond to different stimulus signals which include pH, light and redox. These changes caused by different extenal signals may be achived by different mechanisms. In order to explain the process mentioned above clearly, different features, mechanisms of action, and potent applications of these gatekeepers based on CDs will be discussed in the following parts. In addition, mechanisms of inclusion complexes based on host-guest interaction of CDs with different guest molecules and chemical structures of the MSNs-gatekeepers were shown in Fig 1 and table 1 respectively.

Fig. 1 Inclusion complexes based on host-guest interaction of CD and different guest molecules.



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Table 1. Chemical Structures of the MSNs-gatekeepers Category

Chemical Structures

Ref.

MSNs-BzI

(35, 36)

MSNs-Azo

(37, 38)

MSNs-Fc

(39-41)

2. Gatekeepers based on CD-BzI interaction Under near-neutral pH condition, benzimidazole (BzI) is hydrophobic and it can form a stable inclusion complex with β-CD via host-guest interactions (the binding constant is about 1.6×103 M-1) (13). This inclusion complex can block the diffusion channels of MSNs. However, when BzI is protonated, under acidic conditions ( pH < 7), the binding constant between β-CD and BzI decreases dramatically. As a result, BzI is disassociated from the cavity of β-CD. The main reason is that BzI is more easily dissolved in water when it is protonated. In other words, it becomes more hydrophilic, which can weaken interactions of CD with BzI. Huan Meng et al. reported a novel MSNs delivery system based on the function of β-CD nanovalves that can respond to the acid environments (Fig. 2a)(35, 42). First, they immobilized benzimidazole onto MSNs surface. β-CD was then attached to the benzimidazole units using the high affinity between benzimidazole and hydrophobic


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cavity of β-CD. Acid environments can control the movement of β-CD, which can lead to the open or closure of the mesopores. β-CD acted as a macromolecules gate to block and release the loaded drugs because of its unique three dimensional structure. Subsequently, they demonstrated that the CD-BzI complex could be dissociated in acidifying endosomal compartments (pH 72nm > 100nm)(64). Therefore, the control of particle size is also very important factor when multifunctional MSNs were designed. Until now MCM-41, MCM-48 and SBA-15 type MSNs are most researched. Because MCM-41 size and morphology are easily controlled, it is widely used in drug carriers(71).


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6. Conclusion Here, we have reviewed and discussed the advances of different CD-gated MSNs. In the field of drug delivery, CD-gated MSNs were widely used due to their unique properties. Among material science, pharmaceutical science, and biomedical science develops, different nanovalves based on cyclodextrin are being explored for drug delivery of controlled release. However, CD-gated MSNs have yet to reach their full potentiality in biomedical applications. There is still much noteworthy work to be done, including developing advanced stimuli-responsive nanovalves that have higher selectivity, higher sensitivity, and higher spatiotemporal control. These nanovalves can be constructed by polymers, inorganic nanomaterials, nucleic acids, proteins, peptides and polysaccharides. Multi-functional MSNs constructed by CDs is worth a further study. Moreover, targeting molecules, imaging molecules and protective molecules can be assembled simultaneously by host-guest interactions on the surface of the MSNs. MSNs can also carry two or more chemotherapeutic drugs, which can maximize therapeutic efficacy and overcome drug resistance. Furthermore, an innovative approach to treat cancers can be developed when chemotherapy is combined with gene therapy or immunotherapy. In summary, we still have a long way to go for designing efficient, low-toxic and controllable CD-gated MSNs. Only with continuous development and innovation can the great potential of utilizing the CD-gated MSNs in treatment of cancer be realized.

Keywords: Cyclodextrins • Host-guest interactions • Mesoporous Silica • Nanoparticles •Nanovalves

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