4-methyl-4’-butyric acid methyl ester-2,2’-bipyridyl | 220062-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-methyl-4’-butyric acid methyl ester-2,2’-bipyridyl
• 英文别名: 4-methyl-4'-butyric acid methyl ester-2,2'-bipyridyl；Methyl 4-[2-(4-methylpyridin-2-yl)pyridin-4-yl]butanoate
• CAS: 220062-49-7
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: KQTLWUOZYGXQRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-4’-butyric acid methyl ester-2,2’-bipyridyl 、 [Ru(dppz)(dmb"-{CO₂CH₃}₂)]Cl₂ 以 乙醇 、 水 为溶剂， 以73%的产率得到[Ru(dipyrido[3,2-a:2’,3’-c]phenazine)(dmb’’-{CO₂CH₃}₂)(4-methyl-4-butyric acid methyl ester-2,2-bipyridyl)]Cl₂
  参考文献：
  名称：

  Duplex-Selective Ruthenium-Based DNA Intercalators

  摘要：

  AbstractWe report the design and synthesis of small molecules that exhibit enhanced luminescence in the presence of duplex rather than single‐stranded DNA. The local environment presented by a well‐known [Ru(dipyrido[3,2‐a:2′,3′‐c]phenazine)L2]2+‐based DNA intercalator was modified by functionalizing the bipyridine ligands with esters and carboxylic acids. By systematically varying the number and charge of the pendant groups, it was determined that decreasing the electrostatic interaction between the intercalator and the anionic DNA backbone reduced single‐strand interactions and translated to better duplex specificity. In studying this class of complexes, a single RuII complex emerged that selectively luminesces in the presence of duplex DNA with little to no background from interacting with single‐stranded DNA. This complex shows promise as a new dye capable of selectively staining double‐ versus single‐stranded DNA in gel electrophoresis, which cannot be done with conventional SYBR dyes.

  DOI：

  10.1002/chem.201502095

文献信息

• Duplex-selective organometallic DNA intercalators
  申请人：NORTHWESTERN UNIVERSITY

  公开号：US09969759B2

  公开（公告）日：2018-05-15

  Disclosed herein are organometallic complexes and methods of using the same in detecting double stranded DNA or RNA, selectively over single stranded DNA or RNA.

  本文披露了有机金属配合物及其在检测双链DNA或RNA时的使用方法，能够选择性地区分单链DNA或RNA。
• Dipyridophenazine Complexes of Os(II) as Red-Emitting DNA Probes:  Synthesis, Characterization, and Photophysical Properties
  作者：R. Erik Holmlin、Johanna A. Yao、Jacqueline K. Barton

  DOI：10.1021/ic9808955

  日期：1999.1.1

  Polypyridyl complexes of Os(II) bearing one dipyridophenazine (dppz) derivative and two ancillary ligands derived from bipyridine (bpy) or phenanthroline (phen) exhibit emission maxima at similar to 740 nm and average excited-state lifetimes in the 10 ns range upon binding to DNA by preferential intercalation of the dppz ligand. A family of [Os(L-1)(L-2)(L-3)](2+) and [Os(L-1)(2)(L-2)](2+) complexes with simple modifications in the ancillary phen or bpy ligands (L-1 and L-3) as well as the intercalating dppz ligand (L-2) was prepared. By cyclic voltammetry, electron-donating substituents on the ancillary ligands lowered the Os(3+/2+) reduction potential but did not affect the reduction potential of the dppz ligand. A methyl substituent at the 7-, 8-, or 6-position of the dppz ligand shifted the phenazine reduction toward the negative but did not affect the Os(3+/2+) potential. Absorption titrations indicated intercalative binding to DNA with high affinity (K-B similar to 10(6) M-1) for the family of complexes, although at high ratios (50:1) of base pairs to metal, complexes with ancillary 4,7-dimethylphenanthroline or 4,4'-dimethylbipyridine ligands exhibit less hypochromism (26-27%) in the pi-pi* transition on the dppz ligand compared to complexes with 5,6-dimethylphenanthroline (30-37%) or the parent phen (31-35%). By steady-state and time-resolved emission spectroscopy, complexes bound to DNA by intercalation with substituents on the 4,7- or 4,4'-positions of the ancillary phen or bpy displayed lower quantum yields for emission (Phi(em)) compared to complexes with the parent phen, while complexes with methyl substituents on the dppz ligand had the greatest Phi(em). Studies with poly d(AT), poly d(GC), and mixed-sequence DNA revealed that the emission yields are also sequence-dependent. Comparative luminescence studies in CH2Cl2 demonstrated that these effects arise from a combination of (i) the inherent sensitivity of the excited state to ligand structure and (ii) perturbations in DNA binding geometry introduced by substituents on the ancillary and intercalating ligands. Our results clarify the relationships between ligand architecture and emission yield and lifetime in the presence and absence of DNA and illustrate the utility of dppz complexes of Os(II) as luminescent probes for DNA.