Synthetic Methods of Disulfide Bonds Applied in Drug Delivery Systems

被引:15
作者
Wang, Kaiming [1 ]
Liu, Na [1 ]
Zhang, Pei [1 ]
Guo, Yuanyuan [1 ]
Zhang, Yongchun [1 ,2 ]
Zhao, Zhongxi [1 ,3 ]
Luan, Yuxia [1 ]
Li, Shanzhong [3 ]
Cai, Jianhua [3 ]
Cao, Jimin [3 ]
机构
[1] Shandong Univ, Sch Pharmaceut Sci, 44 West Wenhua Rd, Jinan 250012, Shandong, Peoples R China
[2] Qilu Univ Technol, Sch Chem & Pharmaceut Engn, Daxue Rd,Western Univ Sci Pk, Jinan 250353, Shandong, Peoples R China
[3] Jiangsu Shengshi Kangde Biotech Corp, Lianyungang 222006, Jiangsu, Peoples R China
关键词
Disulfane synthesis; disulfide bonds; drug delivery systems; carrier; prodrug; MESOPOROUS SILICA NANOPARTICLES; S-S BOND; POLY(ETHYLENE GLYCOL); IN-VITRO; PREACTIVATED THIOMERS; PEG; PACLITAXEL; POLYMERS; MICELLES; THERAPY;
D O I
10.2174/1385272820666151207194002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Disulfide bond plays an important role in various fields, for example, biochemical processes, industrial and pharmaceutical chemistry, bioconjugates, peptidomimetics and self-assembled monolayers (SAMs) etc. In the past decades, drug delivery systems (DDS) have been widely investigated, and disulfide-based oxidation-reduction responsive DDS is the most promising one. Disulfide bonds have no physiological toxicity and remain stable in human body, and can be broken into a reduced form of glutathione (GSH) via the thiol-disulfide exchange reaction. Moreover, the GSH level in tumor tissues has been known to be at least 4-fold higher than that in normal tissues. Therefore, this specific redox potential in cells stimulates people to design oxidation-reduction responsive DDS for specifically releasing drugs in tumor cells and develop the new methods for the preparation of organic disulfanes. The present review has attempted to comprehensively summarize recent advances on the synthetic methods of disulfide bond in drug delivery systems.
引用
收藏
页码:1477 / 1489
页数:13
相关论文
共 70 条
  • [51] Shell-Sheddable Micelles Based on Dextran-SS-Poly(ε-caprolactone) Diblock Copolymer for Efficient Intracellular Release of Doxorubicin
    Sun, Huanli
    Guo, Bingnan
    Li, Xiaoqing
    Cheng, Ru
    Meng, Fenghua
    Liu, Haiyan
    Zhong, Zhiyuan
    [J]. BIOMACROMOLECULES, 2010, 11 (04) : 848 - 854
  • [52] Biodegradable micelles with sheddable poly(ethylene glycol) shells for triggered intracellular release of doxorubicin
    Sun, Huanli
    Guo, Bingnan
    Cheng, Ru
    Meng, Fenghua
    Liu, Haiyan
    Zhong, Zhiyuan
    [J]. BIOMATERIALS, 2009, 30 (31) : 6358 - 6366
  • [53] Thambi T, 2011, BIOCONJUGATE CHEM, V22, P1924, DOI [10.1021/bc2000969, 10.1021/bc2000963]
  • [54] Polymer Functionalized Graphene Oxide: A Versatile Nanoplatform for Drug/Gene Delivery
    Theodosopoulos, George V.
    Bilalis, Panayiotis
    Sakellariou, Georgios
    [J]. CURRENT ORGANIC CHEMISTRY, 2015, 19 (18) : 1828 - 1837
  • [55] Vibrations of the S-S bond in elemental sulfur and organic polysulfides: a structural guide
    Trofimov, Boris A.
    Sinegovskaya, Lidiya M.
    Gusarova, Nina K.
    [J]. JOURNAL OF SULFUR CHEMISTRY, 2009, 30 (05) : 518 - 554
  • [56] Reductively activated disulfide prodrugs of paclitaxel
    Vrudhula, VM
    MacMaster, JF
    Li, ZG
    Kerr, DE
    Senter, PD
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (24) : 3591 - 3594
  • [57] Redox-responsive mesoporous silica as carriers for controlled drug delivery: A comparative study based on silica and PEG gatekeepers
    Wang, Ying
    Han, Ning
    Zhao, Qinfu
    Bai, Ling
    Li, Jia
    Jiang, Tongying
    Wang, Siling
    [J]. EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2015, 72 : 12 - 20
  • [58] Synthesis and testing of mechanism-based protein-profiling probes for retaining endo-glycosidases
    Williams, SJ
    Hekmat, O
    Withers, SG
    [J]. CHEMBIOCHEM, 2006, 7 (01) : 116 - 124
  • [59] Quantification of thiols and disulfides
    Winther, Jakob R.
    Thorpe, Colin
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 2014, 1840 (02): : 838 - 846
  • [60] Applications properties and synthesis of ω-functionalized n-alkanethiols and disulfides -: the building blocks of self-assembled monolayers
    Witt, D
    Klajn, R
    Barski, P
    Grzybowski, BA
    [J]. CURRENT ORGANIC CHEMISTRY, 2004, 8 (18) : 1763 - 1797