15-(4-碘苯基)十五酸 | 80479-93-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 15-(4-碘苯基)十五酸
• 英文名称: 15-(p-iodophenyl)pentadecanoic acid
• 英文别名: 15-(4-iodophenyl)pentadecanoic acid；omega-(4-iodophenyl)pentadecanoic acid
• CAS: 80479-93-2
• 化学式: C₂₁H₃₃IO₂
• 分子量: 444.396
• InChiKey: YAONEUNUMVOKNQ-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95°C

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi

反应信息

• 作为反应物：
  描述：

  15-(4-碘苯基)十五酸 在 sodium hydroxide 、 sodium iodide 、 苯甲酸 作用下， 以 乙醇 为溶剂， 反应 0.83h， 以80%的产率得到15-(p-[(131)I]iodophenyl)pentadecanoic acid
  参考文献：
  名称：

  Kinetics and mechanism of the nucleophilic exchange reaction of iodide‐131 with 15‐(para‐iodo‐phenyl) pentadecanoic acid

  摘要：

  A procedure for labelling p-IPPA with I-131 by iodine isotope exchange in ethanol using benzoic acid was described. The method results in an overall radiochemical yield of more than 80 % within 50 min. at 170 degrees C. The specific activity of the final product was 10 mCi/mg. The reaction conditions were investigated using Cu(I) in acetic acid, pivalic acid, ammonium acetate and ammonium sulfate. The activation energy of the reaction was calculated to be E = 33.54 Kcal/mol. Quality control of the product was performed by means of high pressure liquid chromatography HPLC.

  DOI：

  10.1002/(sici)1099-1344(199712)39:12<987::aid-jlcr44>3.0.co;2-#
• 作为产物：
  描述：

  1,12-二溴十二烷 在 platinum(IV) oxide sodium hydroxide 、 正丁基锂 、 三正丁胺 、 氢气 、 potassium iodide 、 thallium(III) trifluoroacetate 作用下， 以 乙酸乙酯 为溶剂， 反应 20.25h， 生成 15-(4-碘苯基)十五酸
  参考文献：
  名称：

  Apparu, Marcel; Comet, Michel; Leo, Pierre M., Bulletin de la Societe Chimique de France, 1988, # 1, p. 118 - 124

  摘要：

  DOI：

文献信息

• [EN] NOVEL CHEMICAL AGENTS COMPRISING A CARDIOTONIC MOIETY AND AN IMAGING MOIETY AND METHODS OF THEIR USE<br/>[FR] NOUVEAUX AGENTS CHIMIQUES COMPRENANT UN GROUPE FONCTIONNEL CARDIOTONIQUE ET UN GROUPE FONCTIONNEL D'IMAGERIE, ET PROCEDES D'UTILISATION CORRESPONDANTS
  申请人：BRISTOL MYERS SQUIBB PHARMA CO

  公开号：WO2005042033A1

  公开（公告）日：2005-05-12

  The present invention is directed to novel chemical agents for compounds and their use for imaging myocardial perfusion. The invention also is directed to a kit for forming such novel agents. The chemical agents for the present invention comprising (a) a cardiotonic moiety and (b) an imaging moiety.

  本发明涉及用于化合物的新型化学试剂及其用于成像心肌灌注的应用。本发明还涉及用于形成这种新型试剂的试剂盒。本发明的化学试剂包括（a）一种强心苷部分和（b）一种成像部分。
• Method for monitoring blood flow and metabolic uptake in tissue with radiolabeled alkanoic acid
  申请人：——

  公开号：US20040253177A1

  公开（公告）日：2004-12-16

  The present invention relates to novel modified fatty acid analogs, where a positron or gamma-emitting label is placed at a position on a fatty acid backbone and an organic substituent is substituted at the 2,3; 3,4; 4,5; 5,6 and other sequence positions of a fatty acid backbone. These novel fatty acid analogs are designed to enter the tissues of interest by the same long chain fatty acid carrier mechanism as natural fatty acids, however, functional substituents in the 2,3; 3,4; 4,5; 5,6 and other sequence positions, block the catabolic pathway, thus trapping these analogs in a virtually unmodified form in the tissues of interest.

  本发明涉及新型的改性脂肪酸类似物，其中在脂肪酸骨架的某个位置放置一个正电子或伽马发射标签，并且在脂肪酸骨架的2,3; 3,4; 4,5; 5,6等序列位置上用有机取代基进行取代。这些新型的脂肪酸类似物旨在通过天然长链脂肪酸载体机制进入感兴趣的组织，然而，2,3; 3,4; 4,5; 5,6等序列位置的功能性取代基阻断了分解代谢途径，从而将这些类似物以几乎未修改的形式陷阱在感兴趣的组织中。
• Synthesis and evaluation of radioiodinated terminal para-iodophenyl-substituted .alpha.- and .beta.-methyl-branched fatty acids
  作者：M. M. Goodman、G. Kirsch、F. F. Knapp

  DOI：10.1021/jm00369a027

  日期：1984.3

  long-chain fatty acids. The syntheses and physical properties of 14-(p-iodophenyl)-2(RS)-methyltetradecanoic acid and 15-p-iodophenyl)-3(RS)-methylpentadecanoic acid are described. The radioiodinated agents are of interest as a result of the expected pronounced uptake and prolonged myocardial retention that may result from the inhibition of fatty acid metabolism. Tissue distribution studies in rats

  已经开发出用于制备末端对-偶氮苯基取代的α-和β-甲基支化的长链脂肪酸的方法。描述了14-（对碘苯基）-2（RS）-甲基十四烷酸和15-对碘苯基）-3（RS）-甲基十五烷酸的合成和物理性质。由于预期的明显摄取和延长的心肌滞留（可能由抑制脂肪酸代谢所致），使放射性碘化剂受到关注。在具有14-（对-[125I]碘代苯基）-2（RS）-甲基十四烷酸和15-（对-[125I]碘代苯基）-3（RS）-甲基十五烷酸的大鼠中的组织分布研究显示明显的心脏摄取和长时间保留伴随着体内低碘化和高血脂。放射性碘化甲基支链脂肪酸及其非支链类似物对心脏的摄取比较表明，甲基支链脂肪酸的心肌保留度高于非支链类似物。这些结果表明，由于甲基的存在，心肌滞留的机理是由空间或化学抑制这些脂肪酸的代谢所致。
• Novel design and synthesis of a radioiodinated glycolipid analog as an acceptor substrate for<i>N</i>-acetylglucosaminyltransferase V
  作者：Kenji Arimitsu、Hiroyuki Kimura、Tetsuya Kajimoto、Masahiro Ono、Yoshiro Ohmomo、Masayuki Yamashita、Manabu Node、Hideo Saji

  DOI：10.1002/jlcr.3063

  日期：2013.9

  Guided by the known molecular recognition interactions between N-acetylglucosaminyltransferase V (GnT-V) and certain synthetic substrates, we synthesized a radiolabeled double-stranded glycolipid composed of a long-chain alkyl unit and a radioiodinated phenylalkyl unit, [125I]-2-[N-(2-hydroxy-3-hexadecyloxy)propyl-15-(4-iodophenyl)pentadecanecarboxamido]ethyl 2-acetamido-2-deoxy-β-d-glucopyranosyl-(1→2)-α-d-mannopyranosyl-(1→6)-β-d-glucopyranoside ([125I]2), as a novel intravital glycolipid mimic substrate of GnT-V. The radioactive iodine (125I) was incorporated via iododestannylation of the phenyltributyltin derivative, 2-[N-(2-acetoxy-3-hexadecyloxy)propyl-15-(4-tributylstannylphenyl)pentadecanecarboxamido]ethyl 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-d-glucopyranosyl-(1→2)-3,4,6-O-acetyl-α-d-mannopyranosyl-(1→6)-2,3,4-tri-O-acetyl-β-d-glucopyranoside (26). Subsequent deacetylation at the final step afforded [125I]2.

  在已知的 N-乙酰葡糖胺基转移酶 V（GnT-V）与某些合成底物之间的分子识别相互作用的指导下，我们合成了一种放射性标记的双链糖脂，它由一个长链烷基单元和一个放射性碘化苯基烷基单元组成、[125I]-2-[N-(2-羟基-3-十六烷氧基)丙基-15-(4-碘苯基)十五烷甲酰胺基]乙基 2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖基-(1→2)-α-d-吡喃甘露糖基-(1→6)-β-d-吡喃葡萄糖苷（[125I]2），作为一种新型的 GnT-V 体内糖脂模拟底物。3,4,6-O-三乙酰基-2-乙酰胺基-2-脱氧-β-d-吡喃葡萄糖基-(1→2)-3,4,6-O-乙酰基-α-d-吡喃甘露糖基-(1→6)-2,3,4-O-三乙酰基-β-d-吡喃葡萄糖苷 (26)。随后在最后一步进行脱乙酰化，得到[125I]2。
• System and method for radiographic imaging of tissue
  申请人：——

  公开号：US20010001011A1

  公开（公告）日：2001-05-10

  System and method for radiographic imaging of tissue using a non-radioactive, radio-opaque imaging agent that accumulates intracellularly in tissue in proportion to its functional, or physiological, activity. In one embodiment, the imaging agent is a cell-membrane permeable, radio-opaque, high affinity ligand for the intracellular enzyme hexokinase. The imaging agent is administered to a patient, and after an accumulation interval, radiographic images are acquired. The imaging agent preferentially accumulates in malignant tissue and increases its radio-opacity because of its elevated glucose metabolic rate relative to benign and normal tissue. The tissue being examined is transilluminated by X-ray beams with preselected different mean energy spectra, and a separate radiographic image is acquired during transillumination by each beam. An image processing system performs a weighted combination of the acquired images to produce a single displayed image. The image processing procedure isolates the radiographic density contributed solely by differential accumulation of the imaging agent in malignant, benign, and normal tissue. The system and method thus provides a functional image displayed with the anatomical detail and spatial resolution of a radiographic image. The viewer may interactively control the relative proportion of radiographic density contributed by imaging agent, soft tissue, and bone to the displayed image, allowing the display of functional and anatomical information in complete registration, and facilitating localization of malignant tissue in relation to nearby anatomical structures. In other embodiments, the system and method may be used to detect enzymes, nucleic acids, coenzymes, fatty acids, and other cellular targets in diagnostic imaging applications.

  一种无放射性、放射性不透明成像剂的放射性成像组织的系统和方法，该成像剂在组织内的细胞内积累与其功能或生理活性成比例。在一种实施例中，成像剂是一种细胞膜渗透性、放射性不透明、高亲和力的内源性酶己糖激酶的配体。将成像剂注入患者体内，经过积累时间后获得放射性图像。由于恶性组织的葡萄糖代谢率相对良性和正常组织升高，成像剂更倾向于在恶性组织中积累并增加其放射性。通过预选不同平均能谱的X射线束对被检查的组织进行透照，并在每个束的透照期间获取单独的放射性图像。图像处理系统对所获得的图像进行加权组合，以产生单个显示的图像。图像处理过程仅隔离成像剂在恶性、良性和正常组织中的不同积累所贡献的放射密度。因此，该系统和方法提供了一个功能图像，显示了放射性图像的解剖细节和空间分辨率。观察者可以交互地控制成像剂、软组织和骨骼对显示的图像所贡献的放射密度的相对比例，从而实现功能和解剖信息的完全对齐显示，并促进恶性组织与附近解剖结构的定位。在其他实施例中，该系统和方法可用于检测酶、核酸、辅酶、脂肪酸和其他细胞靶标的诊断成像应用。