mesopurpurin-18 methyl ester | 51671-96-6

• 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: mesopurpurin-18 methyl ester
• 英文别名: (17S)-7,12-diethyl-18t-(2-methoxycarbonyl-ethyl)-3,8,13,17r-tetramethyl-17,18-dihydro-21H,23H-porphine-2,20-dicarboxylic acid anhydride；3-((19S)-8,13-diethyl-4,9,14,18t-tetramethyl-1,3-dioxo-18,19-dihydro-1H,3H,21H,23H-pyrano[3,4,5-ta]porphin-19r-yl)-propionic acid methyl ester；Mesopurpurin-18-methylester；(17S)-15-carboxy-(17rH,18tH)-17,18-dihydro-rhodoporphyrin 13,15-anhydride 17-methyl ester
• CAS: 51671-96-6
• 化学式: C₃₄H₃₆N₄O₅
• 分子量: 580.684
• InChiKey: DXLCZCFIGHHLPW-FRDTYIDUSA-N

物化性质

• 沸点：
  967.9±65.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.99
• 重原子数：
  43.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  127.03
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  mesopurpurin-18 methyl ester 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 51.0h， 生成
  参考文献：
  名称：

  Synthesis of β-Galactose-Conjugated Chlorins Derived by Enyne Metathesis as Galectin-Specific Photosensitizers for Photodynamic Therapy

  摘要：

  A first report on the synthesis and biological evaluation of the beta -galactose-conjugated purpurinimides (a class of chlorins containing a six-membered fused imide ring system) as Gal-1 (galectin-1) recognized photosensitizers, prepared from purpurin-N-propargylimide via enyne metathesis, is discussed. On the basis of examination of the available crystal structure of the galectin-1 N-acetyllactose amine complex, it was considered that the chlorin-based photosensitizers could be introduced into a carbohydrate skeleton to expand the repertoire of the galectin-1-specific ligands. Preliminary molecular modeling analysis utilizing the modeled photosensitizers and the available crystal structures of galectin-carbohydrate complexes indicated that addition of the photosensitizer to the carbohydrate moiety at an appropriate position does not interfere with the galectin-carbohydrate recognition. Under similar drug and light doses, compared to the free purpurinimide analogue, the purpurinimides conjugated either with galactose or with lactose (Gal(beta1-4)-Glc) produced a considerable increase in photosensitizing efficacy in vitro. This indicates the possibility for development of a new class of specific photosensitizers for photodynamic therapy (PDT) based on recognition of a cellular receptor.

  DOI：

  10.1021/jo0105080
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 2.0h， 生成 mesopurpurin-18 methyl ester
  参考文献：
  名称：

  Synthesis, Photophysical, Electrochemical, Tumor-Imaging, and Phototherapeutic Properties of Purpurinimide-N-substituted Cyanine Dyes Joined with Variable Lengths of Linkers

  摘要：

  Purpurinimide methyl esters, bearing variable lengths of N-substitutions, were conjugated individually to a cyanine dye with a carboxylic acid functionality. The results obtained from in vitro and in vivo studies showed a significant impact of the linkers joining the phototherapeutic and fluorescence imaging moieties. The photosensitizer-fluorophore conjugate with a PEG linker showed the highest uptake in the liver, whereas the conjugate linked with two carbon units showed excellent tumor-imaging and PDT efficacy at 24 h postinjection. Whole body imaging and biodistribution studies at variable time points portrayed enhanced fluorescent uptake of the conjugates in the tumor compared to that in the skin. Interestingly, the conjugate with the shortest linker and the one joining with two carbon units showed faster clearance from normal organs, e.g., the liver, kidney, spleen, and lung, compared to that in tumors. Both imaging and PDT efficacy of the conjugates were performed in BALB/c mice bearing Colon26 tumors. Compared to the others, the short linker conjugate showed poor tumor fluorescent properties and as a corollary does not exhibit the dual functionality of the photosensitizer-fluorophore conjugate. For this reason, it was not evaluated for in vivo PDT efficacy. However, in Colon26 tumor cells (in vitro), the short linker was highly effective. Among the conjugates with variable linkers, the rate of energy transfer from the purpurinimide moiety to the cyanine moiety increased with deceasing linker length, as examined by femtosecond laser flash photolysis measurements. No electron transfer from the purpurinimide moiety to the singlet excited state of the cyanine moiety or from the singlet excited state of the cyanine moiety to the purpurinimide moiety occurred as indicated by a comparison of transient absorption spectra with spectra of the one-electron oxidized and one-electron reduced species of the conjugate obtained by spectroelectrochemical measurements.

  DOI：

  10.1021/bc200345p

文献信息

• Syntheses and unusual spectroscopic properties of novel ketobacteriopurpurins
  作者：Andrei N. Kozyrev、Ravindra K. Pandey、Craig J. Medforth、Gang Zheng、Thomas J. Dougherty、Kevin M. Smith

  DOI：10.1016/0040-4039(95)02308-9

  日期：1996.2

  Nuclear Overhauser enhancement experiments show that migratory aptitudes of alkyl groups in various vis-dihydroxybacteriopurpurins are different for individual stereoisomers. Long wavelength absorption maxima of ketobacteriopurpurins obtained from pinacol-pinacolone rearrangements of the corresponding diols are influenced by the position of the keto group in the macrocycle; differences in these maxima

  核Overhauser增强实验表明，对于单个立体异构体，各种vis -dihydroxybacteriopurpurins中的烷基迁移能力不同。从相应二醇的频哪醇-频哪酮重排中获得的酮细菌紫嘌呤的长波长吸收最大值受酮基在大环中的位置的影响。通过引入吸电子取代基可以减小这些最大值之间的差异。
• Synthesis of Novel Benzobacteriopurpurins by Diels-Alder Cycloaddition
  作者：Gang Zheng、Andrei N. Kozyrev、Thomas J. Dougherty、Kevin M. Smith、Ravindra K. Pandey

  DOI：10.1246/cl.1996.1119

  日期：1996.12

  A new class of stable bacteriochlorins, namely benzobacteriopurpurin bearing two exo-cyclic rings was synthesized by way of Diels-Alder cycloaddition of 8-vinyl-mesopurpurin-18 methyl ester with tetracyanoethylene (TCNE) and dimethyl acetylenedicarboxylate (DMAD). These novel bacteriochlorins have long wavelength absorptions in the range of 760 to 795 nm.

  通过8-乙烯基-18-甲基间卟啉与四氰乙烯（TCNE）和二甲基乙炔二羧酸酯（DMAD）的Diels-Alder环加成反应，合成了新型稳定的细菌素，即带有两个外环的苯细菌素卟啉。这些新型细菌素的长波吸收范围在760至795纳米之间。
• Kenner; McCombie; Smith, Journal of the Chemical Society. Perkin transactions I, 1973, vol. 21, p. 2517 - 2523
  作者：Kenner、McCombie、Smith

  DOI：——

  日期：——
• Galectin recognized photosensitizers for photodynamic therapy
  申请人：HEALTH RESEARCH, INC.

  公开号：EP1256586B1

  公开（公告）日：2008-07-09
• Fischer et al., Justus Liebigs Annalen der Chemie, 1936, vol. 524, p. 222,224, 231
  作者：Fischer et al.

  DOI：——

  日期：——