4,5-dihydroxybenzo[a]pyrene | 57304-00-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 4,5-dihydroxybenzo[a]pyrene
• 英文别名: benzo(a)pyrene-4,5-diol；benzo[a]pyrene 4,5-diol；benzo[a]pyrene-4,5-diol
• CAS: 57304-00-4
• 化学式: C₂₀H₁₂O₂
• 分子量: 284.314
• InChiKey: AFDHSXYOTGMEAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯并[a]芘 在 magnesium chloride HepG₂ cells 、 三羟甲基氨基甲烷盐酸盐 、 二甲基亚砜 作用下， 以 水 为溶剂， 反应 72.0h， 生成 苯并(a)芘-7,8-二酮 、 苯并(a)芘-7,8-二醇 、 苯并YR相关化合物9 、 4,5-dihydroxybenzo[a]pyrene
  参考文献：
  名称：

  Modulation of Cytochrome P4501-mediated Bioactivation of Benzo[a]pyrene by Volatile Allyl Sulfides in Human Hepatoma Cells

  摘要：

  烯丙基硫醚，如二烯丙基硫醚（DAS）、二烯丙基二硫化物（DADS）和二烯丙基三硫化物（DATS），是薤白蔬菜的典型风味成分，在动物模型中已被证明可抑制苯并[a]芘（B[a]P）诱导的致癌作用。作为这种抑制作用的可能机制，我们使用人肝癌细胞模型（HepG2）研究了这些挥发性物质对细胞色素 P450 (CYP)1（CYP1A1、1A2 和 1B1）介导的 B[a]P 生物活化的影响。在 100-1,000 μM 浓度下，DADS 和 DATS 对 B[a]P 诱导的乙氧基瑞香素 O-脱乙基酶（EROD）活性（一种 CYP1 的标记酶）的抑制率分别为 30%-90% 和 70%-95%。细胞存活率是抑制 B[a]P 生物活化能力的指标，100-1,000 μM DADS 和 10-100 μM DATS 处理可提高细胞存活率。免疫印迹结果表明，B[a]P 诱导的 CYP1A2 蛋白受到 100-1,000 μM 的 DADS 和 10-100 μM 的 DATS 的抑制，但在任何微粒体中都检测不到 CYP1A1 和 1B1。对 B[a]P 代谢物的分析表明，与对照组相比，在 DADS 和 DATS 处理过的微粒体中形成的 7,8-二醇水平明显降低。烯丙基硫醚处理也降低了形成的 9,10-二醇和 4,5-二醇的水平。这些结果表明，烯丙基硫醚对 B[a]P 诱导的癌变的保护机制可能与调节 CYP1 介导的 B[a]P 生物活化有关。

  DOI：

  10.1271/bbb.65.2205

文献信息

• SILICA ENCAPSULATED BIOMATERIALS
  申请人：Wackett Lawrence P.

  公开号：US20140051144A1

  公开（公告）日：2014-02-20

  The present invention relates to compositions for encapsulation of biomaterials in a silica-matrix. The present invention includes a composition for formation of a silica-matrix encapsulated biomaterial. The composition includes a reactive silicon compound and a biomaterial with a catalytic activity. When encapsulated in the silica-matrix, the biomaterial at least partially retains its catalytic activity. The present invention also relates to methods of making silica-matrix encapsulated biomaterials, and to methods of using silica-matrix encapsulated biomaterials, including methods of treating water or gas using the silica-matrix encapsulated biomaterials.
• US9790484B2
  申请人：——

  公开号：US9790484B2

  公开（公告）日：2017-10-17
• [EN] SILICA ENCAPSULATED BIOMATERIALS<br/>[FR] BIOMATÉRIAUX ENCAPSULÉS DANS DE LA SILICE
  申请人：WACKETT LAWRENCE P

  公开号：WO2012116013A2

  公开（公告）日：2012-08-30

  The present invention relates to compositions for encapsulation of biomaterials in a silica-matrix. The present invention includes a composition for formation of a silica-matrix encapsulated biomaterial. The composition includes a reactive silicon compound and a biomaterial with a catalytic activity. When encapsulated in the silica-matrix, the biomaterial at least partially retains its catalytic activity. The present invention also relates to methods of making silica-matrix encapsulated biomaterials, and to methods of using silica-matrix encapsulated biomaterials, including methods of treating water or gas using the silica-matrix encapsulated biomaterials.
• Modulation of Cytochrome P4501-mediated Bioactivation of Benzo[a]pyrene by Volatile Allyl Sulfides in Human Hepatoma Cells
  作者：Hyang Sook CHUN、Hyun Jung KIM、Eun Hye CHOI

  DOI：10.1271/bbb.65.2205

  日期：2001.1

  Allyl sulfides such as diallyl sulfide (DAS), diallyl disulfide (DADS), and diallyl trisulfide (DATS), typical flavor components of Allium vegetables, have been shown to inhibit benzo[a]pyrene (B[a]P)-induced carcinogenesis in animal models. As a possible mechanism of this inhibition, the effect of these volatile substances on cytochrome P450 (CYP)1 (CYP1A1, 1A2 and 1B1)-mediated bioactivation of B[a]P was investigated using a human hepatoma cell model (HepG2). DADS and DATS inhibited the B[a]P-induced ethoxyresorufin O-deethylase (EROD) activity, a marker enzyme for CYP1, by 30-90% and 70-95% at 100-1,000 μM concentration, respectively. The cell viability, an indicator of the capacity to inhibit B[a]P bioactivation, was increased by treatments of 100-1,000 μM DADS and 10-100 μM DATS. Immunoblot results indicated that the B[a]P inducible CYP1A2 protein was suppressed by 100-1,000 μM of DADS and 10-100 μM of DATS, but CYP1A1 and 1B1 were not detectable in any microsomes. Analysis of B[a]P metabolites revealed that the level of 7,8-diol formed was significantly reduced in the DADS and DATS treated microsomes as compared to the control. The level of 9,10-diol and 4,5-diol formed was also lowered by the allyl sulfide treatments. These results suggest that the protective mechanism of allyl sulfides on B[a]P-induced carcinogenesis is possibly related with the modulation of CYP1-mediated bioactivation of B[a]P.

  烯丙基硫醚，如二烯丙基硫醚（DAS）、二烯丙基二硫化物（DADS）和二烯丙基三硫化物（DATS），是薤白蔬菜的典型风味成分，在动物模型中已被证明可抑制苯并[a]芘（B[a]P）诱导的致癌作用。作为这种抑制作用的可能机制，我们使用人肝癌细胞模型（HepG2）研究了这些挥发性物质对细胞色素 P450 (CYP)1（CYP1A1、1A2 和 1B1）介导的 B[a]P 生物活化的影响。在 100-1,000 μM 浓度下，DADS 和 DATS 对 B[a]P 诱导的乙氧基瑞香素 O-脱乙基酶（EROD）活性（一种 CYP1 的标记酶）的抑制率分别为 30%-90% 和 70%-95%。细胞存活率是抑制 B[a]P 生物活化能力的指标，100-1,000 μM DADS 和 10-100 μM DATS 处理可提高细胞存活率。免疫印迹结果表明，B[a]P 诱导的 CYP1A2 蛋白受到 100-1,000 μM 的 DADS 和 10-100 μM 的 DATS 的抑制，但在任何微粒体中都检测不到 CYP1A1 和 1B1。对 B[a]P 代谢物的分析表明，与对照组相比，在 DADS 和 DATS 处理过的微粒体中形成的 7,8-二醇水平明显降低。烯丙基硫醚处理也降低了形成的 9,10-二醇和 4,5-二醇的水平。这些结果表明，烯丙基硫醚对 B[a]P 诱导的癌变的保护机制可能与调节 CYP1 介导的 B[a]P 生物活化有关。