GlnTrpAlaValGlyHisLeuMetNH2 | 55749-99-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: GlnTrpAlaValGlyHisLeuMetNH2
• 英文别名: (2S)-2-amino-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide
• CAS: 55749-99-0
• 化学式: C₄₃H₆₅N₁₃O₉S
• 分子量: 940.137
• InChiKey: VZGJNCHEUPMLPM-DGKZTOLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  66
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  386
• 氢给体数：
  12
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-琥珀酰亚胺 3-碘苯甲酸酯 、 GlnTrpAlaValGlyHisLeuMetNH2 在 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 1.67h， 以62.3%的产率得到
  参考文献：
  名称：

  Preliminary Evaluation of Astatine-211-Labeled Bombesin Derivatives for Targeted Alpha Therapy

  摘要：

  There are various diagnostic and therapeutic agents for prostate cancer using bombesin (BBN) derivatives, but astatine-211 (At-211)-labeled BBN derivatives have yet to be studied. This study presented a preliminary evaluation of At-211- labeled BBN derivative. Several nonradioactive iodine-introduced BBN derivatives (IB-BBNs) with different linkers were synthesized and their binding affinities measured. Because IB-3 exhibited a comparable affinity to native BBN, [At-211]AB-3 was synthesized and the radiochemical yields of [At-211] AB-3 was 28.2 +/- 2.4%, with a radiochemical purity of >90%. The stability studies and cell internalization/externalization experiments were performed. [At-211]AB-3 was taken up by cells and internalized; however, radioactivity effluxed from cells over time. In addition, the biodistribution of [At-211]AB-3, with and without excess amounts of BBN, were evaluated in PC-3 tumor-bearing mice. Despite poor stability in murine plasma, [At-211]AB-3 accumulated in tumor tissue (4.05 +/- 0.73%ID/g) in PC-3 tumor-bearing mice, which was inhibited by excess native BBN (2.56 +/- 0.24%ID/g). Accumulated radioactivity in various organs is probably due to free At-211. Peptide degradation in murine plasma and radioactivity efflux from cells are areas of improvement. The development of At-211-labeled BBN derivatives requires modifying the BBN sequence and preventing deastatination.

  DOI：

  10.1248/cpb.c20-00077
• 作为产物：
  描述：

  DL-缬氨酸 在 N-乙基吗啉 、 盐酸 、 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 sodium hydroxide 、 溶剂黄146 为溶剂， 反应 50.0h， 生成 GlnTrpAlaValGlyHisLeuMetNH2
  参考文献：
  名称：

  Synthesis of C-terminal fragments of bombesin and their analogues

  摘要：

  DOI：

  10.1007/bf00597661

文献信息

• Trifunctional^99mTc based radiopharmaceuticals: metal-mediated conjugation of a peptide with a nucleus targeting intercalator
  作者：Karel Zelenka、Lubor Borsig、Roger Alberto

  DOI：10.1039/c0ob00504e

  日期：——

  The development of molecular imaging agents with multiple functions has become a major trend in radiopharmaceutical chemistry. We present herein the syntheses of trifunctional compounds, combining an acridine orange (AO) based intercalator with a GRP receptor specific bombesin like peptide (BBN). Metal-mediated conjugation of these two functions via the [2 + 1] approach to the third function, the [M(CO)3]+ (M = 99mTc, Re) moiety, yielded the final trifunctional molecules. The strongly fluorescent acridine orange, a nuclear targeting agent, has been derivatised with 4-imidazolecarboxylate as a bidentate ligand and bombesin with an isonitrile group as a monodentate ligand. For cell and nuclear uptake studies, [Re(L1-BBN)(L2-Ical)(CO)3] type complexes were synthesized and characterized. For radiopharmaceutical purposes, the 99mTc analogues have been prepared in a stepwise synthesis. Fluorescence microscopy studies on PC-3 cells, bearing the BBN receptor, showed high and rapid uptake into the cytoplasm. For the bifunctional molecule, lacking the BBN peptide, no internalization was observed.

  多功能分子成像剂的发展已成为放射性药物化学的主要趋势。本文介绍了三功能化合物的合成，这些化合物结合了以吖啶橙（AO）为基础的插入剂和GRP受体特异性类似bombesin的肽（BBN）。通过[2 + 1]方法，将这两种功能与第三种功能[M(CO)3]+（M = 99mTc，Re）部分进行金属介导的连接，得到了最终的三功能分子。作为核靶向剂，吖啶橙具有强烈的荧光，衍生化为双齿配体4-咪唑羧酸酯，bombesin则带有异氰基作为单齿配体。为了研究细胞和核摄取，我们合成了并表征了[Re(L1-BBN)(L2-Ical)(CO)3]型配合物。为了放射性药物的目的，我们采用逐步合成法合成了99mTc类似物。对携带BBN受体的PC-3细胞进行荧光显微镜研究，结果显示细胞质中的摄取率高且迅速。对于缺乏BBN肽的双功能分子，未观察到内化现象。
• GASTRIN RELEASING PEPTIDE COMPOUNDS
  申请人：Cappelletti Enrico

  公开号：US20110052491A1

  公开（公告）日：2011-03-03

  New and improved compounds for use in diagnostic imaging or therapy having the formula M—N—O—P—G, wherein M is an optical label or a metal chelator (in the form complexed with a metal radionuclide or not), N—O—P is the linker, and G is the GRP receptor targeting peptide. Methods for imaging a patient and/or providing radiotherapy or phototherapy to a patient using the compounds of the invention are also provided. Methods and kits for preparing a diagnostic imaging agent from the compound is further provided. Methods and kits for preparing a radiotherapeutic agent are further provided.

  本发明涉及用于诊断成像或治疗的新型化合物，其化学式为M—N—O—P—G，其中M是光学标记或金属螯合剂（以与金属放射性核素形成络合物或非络合形式存在），N—O—P是连接剂，G是GRP受体靶向肽。本发明还提供了使用该化合物进行患者成像和/或提供放射治疗或光疗的方法。本发明还提供了制备诊断成像剂的方法和试剂盒。本发明还提供了制备放射治疗剂的方法和试剂盒。
• KURANOVA, I. L.;CHURKINA, S. I.;LYUDMIROVA, V. L.;FILONOVA, E. B.;IBATULL+, XIMIYA PRIROD. SOED.,(1989) N, S. 554-564
  作者：KURANOVA, I. L.、CHURKINA, S. I.、LYUDMIROVA, V. L.、FILONOVA, E. B.、IBATULL+

  DOI：——

  日期：——
• IMPROVED LINKERS FOR PHARMACEUTICAL COMPOUNDS
  申请人：Bracco Imaging, S.P.A.

  公开号：EP1583564A2

  公开（公告）日：2005-10-12
• EP1583564A4
  申请人：——

  公开号：EP1583564A4

  公开（公告）日：2007-06-13