fluorescein 5-isothiocyanate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: fluorescein 5-isothiocyanate
• 英文别名: fluorescein-5-isothiocyanate；fluorescein isothiocyanate；fluorescein 5-thiocyanate；FITC；2-(3-Hydroxy-6-oxo-8a,9-dihydroxanthen-9-yl)-5-isothiocyanatobenzoic acid
• 化学式: C₂₁H₁₃NO₅S
• 分子量: 391.404
• InChiKey: KDYBEHLSATXMBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  fluorescein 5-isothiocyanate 在 ammonium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到fluorescein 5-thiourea
  参考文献：
  名称：

  Colorectal delivery and retention of PEG-Amprenavir-Bac7 nanoconjugates—proof of concept for HIV mucosal pre-exposure prophylaxis

  摘要：

  Local delivery of anti-HIV drugs to the colorectal mucosa, a major site of HIV replication, and their retention within mucosal tissue would allow for a reduction in dose administered, reduced dosing frequency and minimal systemic exposure. The current report describes a mucosal pre-exposure prophylaxis (mPrEP) strategy that utilizes nanocarrier conjugates (NC) consisting of poly(ethylene glycol) (PEG), amprenavir (APV), and a cell-penetrating peptide (CPP; namely Bac7, a fragment derived from bactenecin 7). APV-PEG NCs with linear PEGs (2, 5, 10, and 30 kDa) exhibited reduced (52–21 %) anti-HIV-1 protease (PR) activity as compared to free APV in an enzyme-based FRET assay. In MT-2 T cells, APV-PEG3.4 kDa-FITC (APF) anti-HIV-1 activity was significantly reduced (160-fold, IC50 = 8064 nM) due to poor cell uptake, whereas it was restored (IC50 = 78.29 nM) and similar to APV (IC50 = 50.29 nM) with the addition of Bac7 to the NC (i.e., APV-PEG3.4 kDa-Bac7, APB). Flow cytometry and confocal microscopy demonstrated Bac7-PEG3.4 kDa-FITC (BPF) uptake was two- and fourfold higher than APF in MT-2 T cells and Caco-2 intestinal epithelial cells, respectively. There was no detectable punctate fluorescence in either cell line suggesting that BPF directly enters the cytosol thus avoiding endosomal entrapment. After colorectal administration in mice, BPF mucosal concentrations were 21-fold higher than APF concentrations. BPF concentrations also remained constant for the 5 days of the study suggesting that (1) the NC’s structural characteristics (i.e., the size of the PEG carrier and the presence of a CPP) significantly influenced tissue persistence, and (2) the NCs were probably lodged in the lamina propria since the average rodent colon mucosal cell turnover time is 2–3 days. These encouraging results suggest that Bac7 functionalized NCs delivered locally to the colorectal mucosa may form drug delivery depots that are capable of sustaining colorectal drug concentrations. Although the exact mechanisms for tissue persistence are unclear and will require further study, these results provide proof-of-concept feasibility for mPrEP.

  DOI：

  10.1007/s13346-015-0269-4

文献信息

• Synthesis and evaluation of [14C]-Labelled and fluorescent-Tagged paclitaxel derivatives as new biological probes
  作者：Ch.Srinivasa Rao、Jao-Jia Chu、Rai-Shung Liu、Yiu-Kay Lai

  DOI：10.1016/s0968-0896(98)00158-8

  日期：1998.11

  results in this report demonstrate that (a) the new paclitaxel derivatives 4, 9, 11 could be prepared with good yields starting from paclitaxel; (b) the [14C]acetylation step was found to be better by using [14C]acetic anhydride rather than [14C]sodium acetate; (c) the radiochemical purity of 4 was 96% and its specific activity was 48 mCi/mmol; (d) the cytotoxicity of 4 was close to that of paclitaxel

  我们的本报告涉及迄今未报道的7-（[[羰基-14C]-乙酰基]紫杉醇4和两种新的生物活性7取代的荧光紫杉烷类化合物（FITC 9和若丹明11）的制备，以及对其作为生物探针的应用的评价。本报告中的结果表明：（a）从紫杉醇开始可以制备高收率的新紫杉醇衍生物4、9、11；（b）发现通过使用[14C]乙酸酐而不是[14C]乙酸钠，[14C]乙酰化步骤更好。（c）4的放射化学纯度为96％，比活为48 mCi / mmol；（d）4的细胞毒性接近紫杉醇，而9，11的活性远低于紫杉醇，但这些细胞毒性水平足以满足其生物学应用；（e）事实证明，使用9和11进行的流式细胞术定量分析药物与使用4进行的基于放射性的测定具有同等效率；（f）在两种情况下，通过9和11进行的细胞内荧光定位都是有效的，并且微管网络模式可见。（g）11时总体荧光成像效率更好，而9时荧光强度更高；（h）在9和11的荧光研究中均观察到了核仁染
• Fluorescently Labeled Amino Acids as Building Blocks for Bioactive Molecules
  作者：Michael Gütschow、Daniela Häußler

  DOI：10.1055/s-0035-1560361

  日期：——

  A series of twelve fluorescently labeled amino acids were designed by assembling different coumarin, fluorescein, or nitrobenzofurazan fluorophores with N-protected lysine or 2-aminopropionic acid. The synthesized amino acids were evaluated with regard to their spectroscopic properties. The easy introduction of the amino acids into peptides and peptidomimetics was exemplarily shown for one coumarin-labeled amino acid.
• Discovery of Two Classes of Potent Glycomimetic Inhibitors of <i>Pseudomonas aeruginosa</i> LecB with Distinct Binding Modes
  作者：Dirk Hauck、Ines Joachim、Benjamin Frommeyer、Annabelle Varrot、Bodo Philipp、Heiko M. Möller、Anne Imberty、Thomas E. Exner、Alexander Titz

  DOI：10.1021/cb400371r

  日期：2013.8.16

  The treatment of infections due to the opportunistic pathogen Pseudomonas aeruginosa is often difficult, as a consequence of bacterial biofilm formation. Such a protective environment shields the bacterium from host defense and antibiotic treatment and secures its survival. One crucial factor for maintenance of the biofilm architecture is the carbohydrate-binding lectin LecB. Here, we report the identification of potent mannose-based LecB inhibitors from a screening of four series of mannosides in a novel competitive binding assay for LecB. Cinnamide and sulfonamide derivatives are inhibitors of bacterial adhesion with up to a 20-fold increase in affinity to LecB compared to the natural ligand methyl mannoside. Because many lectins of the host require terminal saccharides (e.g., fucosides), such capped structures as reported here may offer a beneficial selectivity profile for the pathogenic lectin. Both classes of compounds show distinct binding modes at the protein, offering the advantage of a simultaneous development of two new lead structures as anti-pseudomonadal drugs with an anti-virulence mode of action.
• Dna enzyme and method for controlling activity thereof
  申请人：Asanuma Hiroyuki

  公开号：US20070203331A1

  公开（公告）日：2007-08-30

  A DNA enzyme having the RNA cleavage activity significantly improved as compared with those of known DNA enzymes and a method for controlling the activity, the method being capable of reversibly controlling the RNA cleavage activity of the DNA enzyme by light irradiation, are provided. The DNA enzyme includes a nucleotide residue, to which any one organic group selected from the group consisting of azobenzene, spiropyran, stilbene, and derivatives thereof is bonded, at a 3′-side end of a catalytically active loop of the DNA enzyme. The method for controlling the activity includes the step of applying light at specific wavelengths to the DNA enzyme including a nucleotide residue, to which any one organic group selected from the group consisting of azobenzene, spiropyran, stilbene, and derivatives thereof is bonded, and thereby, effecting reversible structural isomerization between a planar structure and a nonplanar structure of the organic group, so as to control the RNA cleavage activity of the DNA enzyme.
• Colorectal delivery and retention of PEG-Amprenavir-Bac7 nanoconjugates—proof of concept for HIV mucosal pre-exposure prophylaxis
  作者：Mahta Samizadeh、Xiaoping Zhang、Simi Gunaseelan、Antoinette G. Nelson、Matthew S. Palombo、Daniel R. Myers、Yashveer Singh、Usha Ganapathi、Zoltan Szekely、Patrick J. Sinko

  DOI：10.1007/s13346-015-0269-4

  日期：2016.2

  Local delivery of anti-HIV drugs to the colorectal mucosa, a major site of HIV replication, and their retention within mucosal tissue would allow for a reduction in dose administered, reduced dosing frequency and minimal systemic exposure. The current report describes a mucosal pre-exposure prophylaxis (mPrEP) strategy that utilizes nanocarrier conjugates (NC) consisting of poly(ethylene glycol) (PEG), amprenavir (APV), and a cell-penetrating peptide (CPP; namely Bac7, a fragment derived from bactenecin 7). APV-PEG NCs with linear PEGs (2, 5, 10, and 30 kDa) exhibited reduced (52–21 %) anti-HIV-1 protease (PR) activity as compared to free APV in an enzyme-based FRET assay. In MT-2 T cells, APV-PEG3.4 kDa-FITC (APF) anti-HIV-1 activity was significantly reduced (160-fold, IC50 = 8064 nM) due to poor cell uptake, whereas it was restored (IC50 = 78.29 nM) and similar to APV (IC50 = 50.29 nM) with the addition of Bac7 to the NC (i.e., APV-PEG3.4 kDa-Bac7, APB). Flow cytometry and confocal microscopy demonstrated Bac7-PEG3.4 kDa-FITC (BPF) uptake was two- and fourfold higher than APF in MT-2 T cells and Caco-2 intestinal epithelial cells, respectively. There was no detectable punctate fluorescence in either cell line suggesting that BPF directly enters the cytosol thus avoiding endosomal entrapment. After colorectal administration in mice, BPF mucosal concentrations were 21-fold higher than APF concentrations. BPF concentrations also remained constant for the 5 days of the study suggesting that (1) the NC’s structural characteristics (i.e., the size of the PEG carrier and the presence of a CPP) significantly influenced tissue persistence, and (2) the NCs were probably lodged in the lamina propria since the average rodent colon mucosal cell turnover time is 2–3 days. These encouraging results suggest that Bac7 functionalized NCs delivered locally to the colorectal mucosa may form drug delivery depots that are capable of sustaining colorectal drug concentrations. Although the exact mechanisms for tissue persistence are unclear and will require further study, these results provide proof-of-concept feasibility for mPrEP.