Methyl Bacteriopheophorbide a | 569-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: Methyl Bacteriopheophorbide a
• 英文别名: 3¹-oxo-rhodobacteriochlorin 17³-methyl ester；bacteriopheophorbide a methyl ether；methyl bacteriopheophorbide-a；bacteriopheophorbide a；bacteriopheophorbide-a-methyl ester；Bacteriophaeophorbid-a-methylester
• CAS: 569-54-0
• 化学式: C₃₆H₄₀N₄O₆
• 分子量: 624.737
• InChiKey: IPYJFZCXFJSRIC-JWBYUVNJSA-N

物化性质

• 熔点：
  222-224 °C
• 沸点：
  900.1±65.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  46.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  144.1
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methyl Bacteriopheophorbide a 在 吡啶 、 氢氧化钾 、 乙醚 作用下， 生成 3-acetylbacteriochlorin 15-glyoxylic acid trimethyl ester
  参考文献：
  名称：

  Fischer; Lambrecht; Mittenzwei, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1938, vol. 253, p. 12,36

  摘要：

  DOI：
• 作为产物：
  描述：

  bacteriopheophytin a 在 4-二甲氨基吡啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三氟乙酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 Methyl Bacteriopheophorbide a
  参考文献：
  名称：

  Modulation of Reactive Oxygen Species Photogeneration of Bacteriopheophorbide a Derivatives by Exocyclic E-Ring Opening and Charge Modifications

  摘要：

  With the knowledge that the dominant photodynamic therapy (PDT) mechanism of la (WST09) switched from type 2 to type 1 for 1b (WST11) upon taurine-driven E-ring opening, we hypothesized that taurine-driven E-ring opening of bacteriochlorophyll derivatives and net-charge variations would modulate reactive oxygen species (ROS) photogeneration. Eight bacteriochlorophyll a derivatives were synthesized with varying charges that either contained the E ring (2a-5a) or were synthesized by taurine-driven E-ring opening (2b-513). Time-dependent density functional theory (TDDFT) modeling showed that all derivatives would be type 2 PDT-active, and ROS-activated fluorescent probes were used to investigate the photogeneration of a combination of type 1 and type 2 PDT ROS in organic- and aqueous-based solutions. These investigations validated our predictive modeling calculations and showed that taurine-driven E-ring opening and increasing negative charge generally enhanced ROS photogeneration in aqueous solutions. We propose that these structure activity relationships may provide simple strategies for designing bacteriochlorins that efficiently generate ROS upon photoirradiation.

  DOI：

  10.1021/jm401538h

文献信息

• [EN] METHODS FOR MAKING BACTERIOCHLORIN MACROCYCLES COMPRISING AN ANNULATED ISOCYCLIC RING AND RELATED COMPOUNDS<br/>[FR] PROCÉDÉS DE FABRICATION DE MACROCYCLES BACTÉRIOCHLORINES COMPRENANT UN NOYAU ISOCYCLIQUE ANNELÉ ET DES COMPOSÉS APPARENTÉS
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2018102252A1

  公开（公告）日：2018-06-07

  Described herein are bacteriochlorins comprising an annulated isocyclic ring. Also described are methods and intermediates for the synthesis of bacteriochlorins comprising an annulated isocyclic ring, and methods of using such bacteriochlorins for, among other things, diagnostic and therapeutic purposes such as, e.g., luminescent compounds in flow cytometry, and/or as active agents in photodynamic therapy (PDT).

  本文描述了包含环接合异环戊二烯环的细菌叶绿素。还描述了合成包含环接合异环戊二烯环的细菌叶绿素的方法和中间体，以及利用这种细菌叶绿素进行诊断和治疗等用途的方法，例如，在流式细胞术中用作发光化合物，和/或作为光动力疗法（PDT）中的活性剂。
• OXO-BACTERIOPYROPHEOPHORBIDE-A CARBOXYLIC ACID AND ESTERS THEREOF
  申请人：Pandey K. Ravindra

  公开号：US20060111565A1

  公开（公告）日：2006-05-25

  A compound having the structural formula: where R is H or lower alkyl of 1 through 12 carbon atoms. In general, the compounds of the invention are 13 2 -Oxo-bacteriopyropheophorbide-a carboxylic acid and C 1 -C 12 alkyl esters thereof. A method for the preparation of the carboxylic acid compounds of the invention includes the step of reacting bacteriopyropheophorbide-a alkyl ester with lithium hydroxide in tetrahydrofuran and water. A method of the invention for the preparation of the C 1 -C 12 alkyl ester compounds of the invention includes the steps of reacting bacteriopyropheophorbide-a alkyl, especially methyl, ester with lithium hydroxide in tetrahydrofuran and water to obtain 13 2 -Oxo-bacterio-pyropheophobide-a carboxylic acid followed by reacting the carboxylic acid with an acid chloride producing reagent to obtain the 13 2 -Oxo-bacterio pyropheophobide-a acid chloride (compound 5) and reacting the 13 2 -Oxo-bacterio pyropheophobide-a acid chloride with a C 1 -C 12 alcohol to obtain a 13 2 -Oxo-bacterio-pyropheophobide-a carboxylic acid C 1 -C 12 alkyl ester (compound 6). The compounds of the invention may be used as long wavelength absorbing photosensitizers for photodynamic therapy.

  一种具有结构式的化合物：其中 R 为1至12个碳原子的H或较低烷基。一般来说，该发明的化合物是132-氧代细菌吸光素-a羧酸及其C1-C12烷基酯。该发明的羧酸化合物的制备方法包括将细菌吸光素-a烷基酯与氢氧化锂在四氢呋喃和水中反应的步骤。该发明的C1-C12烷基酯化合物的制备方法包括将细菌吸光素-a烷基（特别是甲基）酯与氢氧化锂在四氢呋喃和水中反应，以获得132-氧代细菌吸光素-a羧酸，然后将羧酸与酸氯化剂反应，得到132-氧代细菌吸光素-a酸氯化物（化合物5），再将132-氧代细菌吸光素-a酸氯化物与C1-C12醇反应，以获得132-氧代细菌吸光素-a羧酸C1-C12烷基酯（化合物6）。该发明的化合物可用作长波长吸收光敏剂，用于光动力疗法。
• A novel bacteriochlorin–styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging
  作者：Pavel A. Panchenko、Mikhail A. Grin、Olga A. Fedorova、Marina A. Zakharko、Dmitriy A. Pritmov、Andrey F. Mironov、Antonina N. Arkhipova、Yuri V. Fedorov、Gediminas Jonusauskas、Raisa I. Yakubovskaya、Natalia B. Morozova、Anastasia A. Ignatova、Alexey V. Feofanov

  DOI：10.1039/c7cp04449f

  日期：——

  The Photosensitizing and fluorescence imaging ability of a bacteriochlorin–naphthalimide conjugate is studied.

  一种细菌叶绿素-萘酰亚胺共轭物的光敏化和荧光成像能力被研究。
• Synthesis and characterization of a new natural product analog, 13²-17³-bacteriochlorophyllone <i>a</i>
  作者：Áron Roxin、Thomas D. MacDonald、Gang Zheng

  DOI：10.1142/s1088424613501058

  日期：2014.3

  Here we show the facile synthesis of 13²-17³-bacteriochlorophyllone a (12), with a distinct seven-membered exocyclic F-ring formed by 13²-17³-cyclization of bacteriopheophorbide a(16). This is the latest reported bacteriochlorin with such an exocyclic F-ring since 1975 (13²-17³ cyclobacteriopheophorbide a-enol, 11), and is an analog of previously described natural exocyclic F-ring-containing porphyrins (1–4) and chlorins (5–10). The structure of 12 was confirmed using a combination of 1D ¹ H NMR, 2D COSY ¹ H NMR, Jmod ¹³ C NMR and HRMS analysis. The biological activity of 12 was explored, and we found that this compound does not possess strong antioxidant activity like its natural product counterparts, but is a capable photosensitizer for photodynamic therapy.

  在这里，我们展示了 132-173-bacteriochlorophyllone a (12) 的简便合成方法，它具有一个独特的七元外环 F-环，是由 132-173 环合细菌合烯醇 a(16)形成的。这是自 1975 年以来最新报道的具有这种外环 F 环的细菌氯素（132-173-环细菌硫杂horbide a-enol，11），与之前描述的天然含外环 F 环的卟啉（1-4）和氯素（5-10）类似。通过一维 1 H NMR、二维 COSY 1 H NMR、Jmod 13 C NMR 和 HRMS 分析，12 的结构得到了确认。我们对 12 的生物活性进行了研究，发现该化合物不像其天然产品那样具有很强的抗氧化活性，但却是一种可用于光动力疗法的光敏剂。
• Antineoplastic agents targeted via glut transporters
  申请人：Zheng Gang

  公开号：US20060171893A1

  公开（公告）日：2006-08-03

  The present invention relates to novel antineoplastic agents and cancer diagnostic agents that specifically target neo-plastic cells via the GLUT transportation system. More specifically, the invention relates to conjugates of 2-deoxyglucose, wherein a linker, which includes a covalent bond, is attached to 2-deoxyglucose at the 2 position, and the linker is attached to a therapeutic or diagnostic agent. The invention also relates to methods of treating tumor disease and methods of making the novel compounds of the present invention. The agents of the present invention are superior to previous agents as they are targeted via GLUT transporters.

  本发明涉及一种新型抗肿瘤剂和癌症诊断剂，该剂能够通过GLUT运输系统特异性地靶向新生肿瘤细胞。更具体地说，本发明涉及2-脱氧葡萄糖的共轭物，其中链接剂包括一个共价键，附着在2-脱氧葡萄糖的2位上，链接剂附着在治疗或诊断剂上。本发明还涉及治疗肿瘤疾病的方法和制备本发明新型化合物的方法。本发明的药剂具有优异的靶向GLUT转运蛋白的特性，比以前的药剂更为优越。