1,3,4,6,8,15-hexahydroxy-13-methyl-7,16-dioxo-7,16-dihydrodibenzo[a,o]perylene-10-carboxylic acid | 60483-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苝醌类
• 英文名称: 1,3,4,6,8,15-hexahydroxy-13-methyl-7,16-dioxo-7,16-dihydrodibenzo[a,o]perylene-10-carboxylic acid
• 英文别名: 7,11,13,16,18,22-Hexahydroxy-24-methyl-9,20-dioxoheptacyclo[13.11.1.12,10.03,8.019,27.021,26.014,28]octacosa-1,3(8),4,6,10,12,14(28),15(27),16,18,21(26),22,24-tridecaene-5-carboxylic acid；7,11,13,16,18,22-hexahydroxy-24-methyl-9,20-dioxoheptacyclo[13.11.1.12,10.03,8.019,27.021,26.014,28]octacosa-1,3(8),4,6,10,12,14(28),15(27),16,18,21(26),22,24-tridecaene-5-carboxylic acid
• CAS: 60483-09-2
• 化学式: C₃₀H₁₆O₁₀
• 分子量: 536.451
• InChiKey: ZMCNJTJBKOIRKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  40
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  193
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,3,4,6,8,15-hexahydroxy-13-methyl-7,16-dioxo-7,16-dihydrodibenzo[a,o]perylene-10-carboxylic acid 在 过氧乙酸 、 磷酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 mono-[123I]iodohypericin monocarboxylic acid
  参考文献：
  名称：

  Synthesis and preliminary evaluation of mono-[123I]iodohypericin monocarboxylic acid as a necrosis avid imaging agent

  摘要：

  Hypericin monocarboxylic acid was synthesized in an overall yield of 25% in four steps and radiolabelled with iodine-123 in good yield (> 75%). The resulting mono-[I-123]iodohypericin monocarboxylic acid was evaluated in normal mice and in rats with ethanol induced liver necrosis. In this model, tracer concentration in necrotic liver tissue was 14 times higher than in the viable liver tissue as quantified by autoradiography at 24 h post injection. The results indicate the feasibility of visualization of necrotic tissue with the novel tracer. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.083
• 作为产物：
  描述：

  大黄素 、 1,3,8-Triacetylemodic acid 在 氢氧化钾 、 对苯二酚 作用下， 反应 120.0h， 生成 1,3,4,6,8,15-hexahydroxy-13-methyl-7,16-dioxo-7,16-dihydrodibenzo[a,o]perylene-10-carboxylic acid
  参考文献：
  名称：

  Synthesis and preliminary evaluation of mono-[123I]iodohypericin monocarboxylic acid as a necrosis avid imaging agent

  摘要：

  Hypericin monocarboxylic acid was synthesized in an overall yield of 25% in four steps and radiolabelled with iodine-123 in good yield (> 75%). The resulting mono-[I-123]iodohypericin monocarboxylic acid was evaluated in normal mice and in rats with ethanol induced liver necrosis. In this model, tracer concentration in necrotic liver tissue was 14 times higher than in the viable liver tissue as quantified by autoradiography at 24 h post injection. The results indicate the feasibility of visualization of necrotic tissue with the novel tracer. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.083

文献信息

• AN IMPROVED SYNTHESIS OF HYPERICIN AND RELATED COMPOUNDS
  作者：Ewa Gruszecka-Kowalik、Leon H. Zalkow

  DOI：10.1080/00304940009356746

  日期：2000.2

  quinone from the traditional medicinal plant St. John's wort (Hypericum genus) has been known for decades.l In recent years, the use of hypericin experienced a renaissance and much attention has been directed to it as a photodynamic agent possessing light-induced antiviral activity against several enveloped viruses, including human immunodeficiency virus (HIV), herpes simplex (HSV), Sindbis virus, murine

  金丝桃素 (3a)，来自传统药用植物圣约翰草（金丝桃属）的天然羟基化多环醌已为人所知数十年。一种光动力剂，对几种包膜病毒具有光诱导的抗病毒活性，包括人类免疫缺陷病毒 (HIV)、单纯疱疹病毒 (HSV)、辛德毕斯病毒、鼠巨细胞病毒 (MCMV)、马传染性贫血病毒 (EIAV)。金丝桃素已被证明可光灭活蛋白激酶 C (PKC)、“琥珀酸氧化酶”、“酪氨酸蛋白激酶 (TPK)3c，并被鉴定为磷脂酰肌醇-3-激酶（PtdIns-3-激酶）抑制剂。'd 光化学，光物理学、立体化学、互变异构化、广泛的研究人员对金丝桃素的光生物学活性和生物医学应用进行了深入研究^。^ 该化合物被证明可以抑制多种肿瘤细胞类型的生长。5 金丝桃素被用作光动力疗法 (PDT) 的新型光敏剂) 和用于诊断应用。h 1957 年，Brockmann 等人发表了第一个多步合成金丝桃素 (3a)，以 3,5-二甲氧基邻苯二甲酸酐和间甲酚开始。一年后，由大黄素蒽酮合成
• Synthesis and preliminary biological evaluation of a99mTc-labeled hypericin derivative as a necrosis avid imaging agent
  作者：Humphrey Fonge、Lixin Jin、Huaijun Wang、Guy Bormans、Yicheng Ni、Alfons Verbruggen

  DOI：10.1002/jlcr.1468

  日期：2008.1

  mono-[123I]iodohypericin monocarboxylic acid are iodine-123-labeled hypericin derivatives which have shown great promise in preclinical studies as necrosis avid imaging agents in animal models of infarction. In view of the more attractive properties of a 99mTc-labeled hypericin derivative, we have synthesized a conjugate of protohypericin monocarboxylic acid with S-benzoylmercaptoacetyldiglycyl-diaminopentane

  单-[123I] 碘金丝桃素和单-[123I] 碘金丝桃素单羧酸是碘-123 标记的金丝桃素衍生物，它们在临床前研究中显示出巨大的前景，作为梗塞动物模型中的坏死狂热显像剂。鉴于 99mTc 标记的金丝桃素衍生物更具吸引力，我们以 15% 的总产率合成了原金丝桃素单羧酸与 S-苯甲酰基巯基乙酰基二氨基戊烷的缀合物。通过在 pH 10 下交换标记以 95% 的标记产率用锝-99m 标记缀合物，然后光环化以产生 99mTc-巯基乙酰二甘氨酰-1,5-二氨基戊烯金丝桃酸甲酰胺 (99mTc-13)。带负电荷的 99mTc-13 复合物通过反相高压液相色谱纯化，测得 log P7.4 为 2.36。在正常的 NMRI 小鼠中，该复合物显示出缓慢的肝胆清除，而血浆清除迅速。通过离体放射自显影、伽马计数和组织化学技术在再灌注肝梗塞大鼠中评估示踪剂。与放射性碘化金丝桃素衍生物不同，新的示踪剂在放射自显影和
• Synthesis, in vitro cellular uptake and photo-induced antiproliferative effects of lipophilic hypericin acid derivatives
  作者：Ivo Crnolatac、Ann Huygens、Arthur van Aerschot、Roger Busson、Jef Rozenski、Peter A.M. de Witte

  DOI：10.1016/j.bmc.2005.09.003

  日期：2005.12

  a series of more lipophilic hypericins. For this purpose, a synthetic pathway to hypericin acid amides with hydrocarbon chains of different lengths stably attached by an amide bond at position C10 was explored. Hypericin acid proved inert in amide forming reactions, whereas the precursor protohypericin acid showed higher reactivity and resulted in the desired amide derivatives, which afterwards can

  金丝桃素是一种天然存在的羟基化菲戊二烯二酮，被用作用于光动力疗法的功能强大的光敏剂，以及用于荧光检测患者膀胱扁平赘生物病变的诊断工具。两种应用都基于该化合物的同质性。为了更深入地了解金丝桃素的某些理化特性会影响其同调尿特性，我们着手合成一系列更多的亲脂性金丝桃素。为此，探索了通过位置C10处的酰胺键稳定连接不同长度烃链的金丝桃素酰胺的合成途径。金丝桃素酸在形成酰胺的反应中被证明是惰性的，而原高丝素酸的前体显示出更高的反应活性并产生了所需的酰胺衍生物，然后可以很容易地转化成它们的菲oper二酮形式。用这种方法成功地合成了金丝桃素酸的己基，辛基，癸基和十二烷基酰胺。使用人类中度分化的非侵入性乳头状移行癌RT-112细胞系，评估了化合物的体外细胞吸收和光诱导的抗增殖作用。尽管更多的亲脂性酰胺被有限地吸收，但是己酰胺积累约5％。以及金丝桃素本身。从抗增殖数据可以进一步得出结论，不仅细胞摄取，而且光
• Synthesis and preliminary evaluation of mono-[123I]iodohypericin monocarboxylic acid as a necrosis avid imaging agent
  作者：Humphrey Fonge、Lixin Jin、Huaijun Wang、Yicheng Ni、Guy Bormans、Alfons Verbruggen

  DOI：10.1016/j.bmcl.2007.04.083

  日期：2007.7

  Hypericin monocarboxylic acid was synthesized in an overall yield of 25% in four steps and radiolabelled with iodine-123 in good yield (> 75%). The resulting mono-[I-123]iodohypericin monocarboxylic acid was evaluated in normal mice and in rats with ethanol induced liver necrosis. In this model, tracer concentration in necrotic liver tissue was 14 times higher than in the viable liver tissue as quantified by autoradiography at 24 h post injection. The results indicate the feasibility of visualization of necrotic tissue with the novel tracer. (C) 2007 Elsevier Ltd. All rights reserved.