(pyroglutamic acid)QKLGNQWAVGHLM-NH2 | 66839-66-5

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: (pyroglutamic acid)QKLGNQWAVGHLM-NH2
• 英文别名: Lys[3]-bombesin
• CAS: 66839-66-5
• 化学式: C₇₁H₁₁₀N₂₂O₁₈S
• 分子量: 1591.86
• InChiKey: DXMFSGIDMUPBCC-FPFNSDSHSA-N

物化性质

• 沸点：
  2075.0±65.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  112
• 可旋转键数：
  51
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  676
• 氢给体数：
  21
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  二苯并环辛烯-琥珀酰亚胺酯 、 (pyroglutamic acid)QKLGNQWAVGHLM-NH2 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以25%的产率得到Aza-DBCO-BN
  参考文献：
  名称：

  应变促进的无铜“点击”化学反应，用于Bombesin的18F放射性标记

  摘要：

  单击以获取PET：通常用于肿瘤核成像的GRP受体特异性肽Bombin可以通过使用无铜的叠氮化物-炔炔“点击”反应以温和快速的方式用18 F标记。一系列叠氮化物可用于提供具有不同疏水性的肽。所得的18 F放射性药物示踪剂（参见方案）在体外在人前列腺癌细胞中保持其对靶向受体的高亲和力。

  DOI：

  10.1002/anie.201105547

文献信息

• Strained alkynes derived from 2,2′-dihydroxy-1,1′-biaryls; synthesis and copper-free cycloaddition with azides
  作者：Alessandro Del Grosso、Lavrentis-Dimitrios Galanopoulos、Cookson K. C. Chiu、Guy J. Clarkson、Peter B. O′ Connor、Martin Wills

  DOI：10.1039/c7ob00991g

  日期：——

  A series of strained alkynes were prepared from 2,2′-dihydroxy-biaryls. Several were characterised by X-ray crystallography, revealing strained C(sp)–C(sp)–C(sp3) bond angles in the range of 163–167°. Their cycloadditions with azides proceed without a catalyst. Functionalised versions of these reagents have potential applications to materials synthesis and bioconjugations.

  由2,2'-二羟基-联芳基制备了一系列应变炔烃。X射线晶体学表征了其中几个，揭示了应变C（sp）–C（sp）–C（sp 3）键角在163–167°范围内。它们与叠氮化物的环加成反应在没有催化剂的情况下进行。这些试剂的功能化版本在材料合成和生物结合方面具有潜在的应用。
• Fully automated peptide radiolabeling from [¹⁸F]fluoride
  作者：Ryan A. Davis、Chris Drake、Robin C. Ippisch、Melissa Moore、Julie L. Sutcliffe

  DOI：10.1039/c8ra10541c

  日期：——

  process is described. First, the prosthetic group, 6-[18F]fluoronicotinyl-2,3,5,6-tetrafluorophenyl ester ([18F]FPy-TFP) was synthesized and subsequently attached to the peptide. The [18F]FPy-peptides were synthesized in 13–26% decay corrected yields from fluorine-18 with high molar activity 1–5 Ci μmol−1 and radiochemical purity of >99% in an overall synthesis time of 97 ± 3 minutes.

  受体靶向肽的生物学特性使其成为流行的诊断成像和治疗药物。通常，用于正电子发射断层扫描 (PET) 成像的氟 18 放射性标记受体靶向肽的合成是一个耗时、复杂、多步骤的合成过程，该过程根据肽的不同而变化很大。与放射性标记途径相关的复杂性和缺乏强大的自动化协议可能会阻碍其向临床的转化。描述了使用 ELIXYS FLEX/CHEM® 放射合成仪分两步从氟 18 中全自动批量生产放射性标记三种肽（YGGFL、cRGDyK 和 Pyr-QKLGNQWAVGHLM）。首先，合成辅基6-[ 18 F]氟烟酰基-2,3,5,6-四氟苯酯([ 18 F]FPy-TFP)，随后将其附着到肽上。 [ 18 F]FPy-肽由氟 18 合成，衰减校正产率为 13-26%，摩尔活性高为 1-5 Ci μmol -1 ，放射化学纯度为 >99%，总合成时间为 97 ± 3 分钟。
• Preliminary Evaluation of Astatine-211-Labeled Bombesin Derivatives for Targeted Alpha Therapy
  作者：Miho Aoki、Songji Zhao、Kazuhiro Takahashi、Kohshin Washiyama、Naoyuki Ukon、Chengbo Tan、Saki Shimoyama、Ken-ichi Nishijima、Kazuma Ogawa

  DOI：10.1248/cpb.c20-00077

  日期：2020.6.1

  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.
• Strain-Promoted Copper-Free “Click” Chemistry for 18F Radiolabeling of Bombesin
  作者：Lachlan S. Campbell-Verduyn、Leila Mirfeizi、Anne K. Schoonen、Rudi A. Dierckx、Philip H. Elsinga、Ben L. Feringa

  DOI：10.1002/anie.201105547

  日期：2011.11.18

  Click for PET: The GRP‐receptor‐specific peptide bombesin, which is often used for nuclear imaging of tumors, can be labeled with 18F in a mild and rapid manner by using a copper‐free azide–alkyne “click” reaction. A range of azides can be used to provide peptides with different hydrophobicities. The resulting 18F radiopharmaceutical tracers (see scheme) maintain their high affinity for the targeted

  单击以获取PET：通常用于肿瘤核成像的GRP受体特异性肽Bombin可以通过使用无铜的叠氮化物-炔炔“点击”反应以温和快速的方式用18 F标记。一系列叠氮化物可用于提供具有不同疏水性的肽。所得的18 F放射性药物示踪剂（参见方案）在体外在人前列腺癌细胞中保持其对靶向受体的高亲和力。