苯并[a]芘-7-醇 | 37994-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 苯并[a]芘-7-醇
• 英文名称: 7-Hydroxybenzo[a]pyrene
• 英文别名: 7-hydroxybenzopyrene；7-hydoxybenzo[a]pyrene；7-hydroxy-BP；7-Hydroxypyren；7-Hydroxybenzopyren；7-Hydroxy-benzo[def]chrysen；7-Hydroxy-benzo[a]pyren；benzo[a]pyrenol-(7)；7-Hydroxybenzo(a)pyrene；benzo[a]pyren-7-ol
• CAS: 37994-82-4
• 化学式: C₂₀H₁₂O
• 分子量: 268.315
• InChiKey: CNQAYISXCZTDQX-UHFFFAOYSA-N

物化性质

• 熔点：
  218.5°C
• 沸点：
  371.47°C (rough estimate)
• 密度：
  1.0921 (rough estimate)
• 溶解度：
  二氯甲烷（微溶）、DMSO（微溶）
• 碰撞截面：
  163.2 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]
• 保留指数：
  3252

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2906299090

SDS

制备方法与用途

类别：有毒物品

可燃性危险特性：

• 可燃
• 燃烧时产生刺激烟雾

储运特性：

• 通风、低温、干燥

灭火剂：

• 干粉
• 泡沫
• 沙土
• 二氧化碳
• 雾状水

反应信息

• 作为反应物：
  描述：

  苯并[a]芘-7-醇 在 硫酸 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到sodium benzopyrene-7-sulphate
  参考文献：
  名称：

  单羟基苯并[ a ] -py的硫酸酯共轭物的合成和稳定性与可能的苯并[ a ] py解毒机理的关系

  摘要：

  1-，3-，7-和9-单羟基苯并[ a ] with与二环己基碳二亚胺（DCC）和H 2 SO 4在二甲基甲酰胺中的反应生成相应的硫酸酯，其在2的pH范围内是稳定的在37°C下达到14。

  DOI：

  10.1039/c3980000598a
• 作为产物：
  描述：

  acetic acid benzo[def]chrysen-7-yl ester 生成 苯并[a]芘-7-醇
  参考文献：
  名称：

  高价碘试剂将多环芳香酚区域特异性氧化成醌类

  摘要：

  高价碘试剂邻碘苯甲酸 (IBX) 和双（三氟乙酰氧基）碘苯 (BTI) 被证明是将多环芳香酚 (PAP) 区域控制氧化成特定异构体（邻、对或远程）的通用试剂。) 的多环芳香醌 (PAQ)。IBX 对一系列PAP的氧化在温和条件下发生，以提供相应的邻位PAQ。相比之下，同一系列PAP与 BTI 的氧化表现出不同的区域特异性，在结构上可行的情况下提供对位PAQ 和邻位-PAQs 或其他情况下的远程 PAQ 异构体。根据高价碘试剂的固有区域选择性以及苯酚前体的结构要求，可以预测形成的特定 PAQ 异构体的结构。IBX 和 BTI 被推荐作为 PAPs 到 PAQs 的区域控制氧化的首选试剂。

  DOI：

  10.1016/j.tet.2009.12.022

文献信息

• UDP-Glycosyltransferase 3A Metabolism of Polycyclic Aromatic Hydrocarbons: Potential Importance in Aerodigestive Tract Tissues
  作者：Ana G. Vergara、Christy J.W. Watson、Gang Chen、Philip Lazarus

  DOI：10.1124/dmd.119.089284

  日期：2020.3

  Polycyclic aromatic hydrocarbons (PAHs) are potent carcinogens and are a primary risk factor for the development of lung and other aerodigestive tract cancers in smokers. The detoxification of PAHs by glucuronidation is well-characterized for the UDP-glycosyltransferase (UGT) 1A, 2A, and 2B subfamilies; however, the role of the UGT3A subfamily in PAH metabolism remains poorly understood. UGT3A enzymes are functionally distinct from other UGT subfamilies (which use UDP-glucuronic acid as a cosubstrate) due to their utilization of alternative cosubstrates (UDP- N -acetylglucosamine for UGT3A1, and UDP-glucose and UDP-xylose for UGT3A2). The goal of the present study was to characterize UGT3A glycosylation activity against PAHs and examine their expression in human aerodigestive tract tissues. In vitro metabolism assays using UGT3A2-overexpressing cell microsomes indicated that UGT3A2 exhibits glycosylation activity against all of the simple and complex PAHs tested. The V max/ K m ratios for UGT3A2 activity with UDP-xylose versus UDP-glucose as the cosubstrate ranged from 0.65 to 4.4 for all PAHs tested, demonstrating that PAH glycosylation may be occurring at rates up to 4.4-fold higher with UDP-xylose than with UDP-glucose. Limited glycosylation activity was observed against PAHs with UGT3A1-overexpressing cell microsomes. While UGT3A2 exhibited low levels of hepatic expression, it was shown by western blot analysis to be widely expressed in aerodigestive tract tissues. Conversely, UGT3A1 exhibited the highest expression in liver with lower expression in aerodigestive tract tissues. These data suggest that UGT3A2 plays an important role in the detoxification of PAHs in aerodigestive tract tissues, and that there may be cosubstrate-dependent differences in the detoxification of PAHs by UGT3A2. SIGNIFICANCE STATEMENT UGT3A2 is highly active against PAHs with either UDP-glucose or UDP-xylose as a cosubstrate. UGT3A1 exhibited low levels of activity against PAHs. UGT3A1 is highly expressed in liver while UGT3A2 is well expressed in extrahepatic tissues. UGT3A2 may be an important detoxifier of PAHs in humans.

  多环芳烃(PAHs)是强致癌物, 是吸烟者发生肺癌及口、咽等上呼吸道和上消化道癌症的首要风险因素。PAHs通过葡萄糖醛酸化反应解毒已在尿苷二磷酸葡糖基转移酶(UDP-glycosyltransferase, UGT)1A、2A和2B亚家族中得到充分阐释, 但UGT3A亚家族在PAH代谢中的作用至今仍未明了。UGT3A酶在功能上与其他亚家族截然不同, 它具有各自的供体底物：对UGT3A1而言是尿苷二磷酸N-乙酰葡糖胺, 而对于UGT3A2则是尿苷二磷酸葡萄糖与尿苷二磷酸木糖。本研究的目的是阐释UGT3A对PAHs的糖基化作用活性, 以及它在人上呼吸道和上消化道组织中的表达。通过UGT3A2过表达细胞微粒体进行的体外代谢实验表明UGT3A2对检测的所有单环和多环PAHs均有糖基化作用活性。以尿苷二磷酸木糖和尿苷二磷酸葡萄糖为供体底物的UGT3A2活性所表现出的V max/K m比率在0.65~4.4之间, 证明PAHs通过UGT3A2进行糖基化反应时, 与底物尿苷二磷酸葡萄糖相比, 底物尿苷二磷酸木糖可提速至4.4倍。UGT3A1过表达细胞微粒体表现出的对PAHs的糖基化作用活性较低。UGT3A2在肝脏中的表达水平偏低, 但通过Western blot分析可知上呼吸道和上消化道组织中的表达水平广泛。相反, UGT3A1则呈现出最高的肝表达量和较低的上呼吸道和上消化道组织表达量。这些数据表明, UGT3A2在上呼吸道和上消化道组织中对PAHs的解毒起着重要作用, 而且PAHs通过UGT3A2的解毒作用可能因供体底物的不同而存在差异。 ［论著意义］UGT3A2对PAHs的活性较强, 供体底物为尿苷二磷酸葡萄糖或尿苷二磷酸木糖。UGT3A1对PAHs只表现出低水平活性。UGT3A1高度表达于肝脏, 而UGT3A2则高度表达于肝外组织。UGT3A2可能是人体内对PAHs的重要解毒酶。
• Facile Multi-gram Preparation of <i>trans</i>-7,8-Dihydro-7,8-dihydroxybenzo[a]pyrene, a Precursor of Benzopyrene Diol Epoxide
  作者：Nobuhito Kurono、Yuji Iwashita、Haruhiko Sugimura

  DOI：10.1080/00304948.2022.2081026

  日期：2022.9.3

  Published in Organic Preparations and Procedures International: The New Journal for Organic Synthesis (Vol. 54, No. 5, 2022)

  发表于国际有机制剂和程序：有机合成新期刊（印刷前，2022 年）
• 8-ARM POLYETHYLENE GLYCOL DERIVATIVE, MANUFACTURING METHOD AND MODIFIED BIO-RELATED SUBSTANCE THEREBY
  申请人：Xiamen Sinopeg Biotech Co., Ltd.

  公开号：EP3315531A1

  公开（公告）日：2018-05-02

  Disclosed are an 8-arm polyethylene glycol (PEG) derivative (formula 1), manufacturing method and modified bio-related substance thereby, wherein a tetravalent group U and four trivalent groups Ec form a highly symmetric octavalent central structure CORE0 together, Lc connects the octavalent center to eight PEG arms having polydiversity or monodiversity and having n1-n8 as the degrees of polymerization thereof. The terminal of one PEG chain is connected to at least one functional group F (k ≥ 1), and said PEG chain and F can be directly connected (g = 0) or connected with a divalent linking group L0 connected with a terminal branched group G (g = 1) therebetween. The latter provides more reacting sites to combine more pharmaceutical molecules, thereby increasing the drug loading capacity. The near-center symmetric structure of the derivative allows more precise control over the molecular weight during large-scale production, thereby facilitating acquisition of a product having a narrower molecular weight distribution. A bio-related substance modified thereby has a more uniform and controllable performance.

  本发明公开了一种 8 臂聚乙二醇（PEG）衍生物（式 1）、其制造方法和改性生物相关物质，其中一个四价基团 U 和四个三价基团 Ec 共同形成一个高度对称的八价中心结构 CORE0，Lc 将八价中心连接到八个 PEG 臂上，这些 PEG 臂具有多元性或单元性，其聚合度为 n1-n8。一条 PEG 链的末端与至少一个官能团 F（k ≥ 1）相连，所述 PEG 链和 F 可以直接相连（g = 0），也可以通过二价连接基 L0 与中间的末端支化基 G（g = 1）相连。后者提供了更多的反应位点，可以结合更多的药物分子，从而提高药物负载能力。衍生物的近中心对称结构可以在大规模生产过程中更精确地控制分子量，从而有利于获得分子量分布更窄的产品。由此改性的生物相关物质具有更均匀、更可控的性能。
• Eight-arm polyethylene glycol derivative, production method therefor, and modified bio-related substance thereof
  申请人：XIAMEN SINOPEG BIOTECH CO., LTD.

  公开号：US10434182B2

  公开（公告）日：2019-10-08

  Disclosed are an eight-arm polyethylene glycol (PEG) derivative (formula I), production method therefor and modified bio-related substance thereby. Wherein, one tetravalent group U together with four trivalent groups Ec form a highly symmetrical octavalent group CORE0; Lc connects the octavalent group to eight PEG chains having polydispersity or monodispersity and having n1 to n8 as the degree of polymerization thereof; the terminal of one PEG chain is connected to at least one functional group F (k≥1); said PEG chain and F therebetween can be directly connected (g=0) or be indirectly connected via a linking group L0 to a terminal end-branching group G (g=1); the latter provides more reactive sites for binding more drug molecules and increases the drug loading. The eight-arm polyethylene glycol derivative has a centrosymmetric or approximately centrosymmetric structure, and leads to more precise control of the molecular weight in large-scale production and much narrower distribution of molecular weight for products. The modified bio-related substance thereby has a more uniform and controllable performance.

  本发明公开了一种八臂聚乙二醇（PEG）衍生物（式 I）、其生产方法及其改性生物相关物质。其中，一个四价基团 U 与四个三价基团 Ec 形成一个高度对称的八价基团 CORE0；Lc 将八价基团连接到八条具有多分散性或单分散性且聚合度为 n1 至 n8 的 PEG 链上；一条 PEG 链的末端与至少一个官能团 F 连接（k≥1）；所述 PEG 链和 F 之间可以直接连接（g=0），也可以通过连接基团 L0 与末端支化基团 G 间接连接（g=1）；后者提供了更多的反应位点，可以结合更多的药物分子，增加药物负载量。八臂聚乙二醇衍生物具有中心对称或近似中心对称结构，因此在大规模生产中可以更精确地控制分子量，产品的分子量分布也更窄。因此，改性生物相关物质的性能更均匀、更可控。
• Multifunctionalized polyethylene glycol derivative and preparation method therefor
  申请人：XIAMEN SINOPEG BIOTECH CO., LTD.

  公开号：US11324827B2

  公开（公告）日：2022-05-10

  Disclosed are a multifunctionalized polyethylene glycol derivative and a preparation method therefor. The derivative has an H-shaped structure as represented by formula (1) and comprises one linear core LPEG and four PEG branch chains, where n1, n2, n3, and n4 respectively are the degrees of polymerization of the branch chains, U1 and U2 are trivalent branching groups connecting the core LPEG to two of the PEG branch chains, F1 and F2 contain a functional group or a protected form R01 thereof and may or may not contain a branched group G, correspondingly, the number of R01 is one or more, F1 and F2 are either identical or different, any one linking group in the molecule or any linking group formed with an adjacent heteroatom group can either remain stable or be degraded, and any one PEG segment in the molecule is discretely polydispersed or monodispersed. The multifunctional polyethylene glycol is flexible and diverse in terms of branch structures and the lengths of branching arms, has various parameters and performance indicators that are adjustable and easy to control, and has a broad applicability.

  本发明公开了一种多功能聚乙二醇衍生物及其制备方法。该衍生物具有由式（1）表示的 H 型结构，包括一个线性核心 LPEG 和四个 PEG 支链，其中 n1、n2、n3 和 n4 分别为支链的聚合度，U1 和 U2 为连接核心 LPEG 和两个 PEG 支链的三价支化基团、F1 和 F2 含有一个官能团或其保护形式 R01，可以含有或不含有支链基团 G，相应地，R01 的数目为一个或多个，F1 和 F2 要么相同要么不同，分子中的任何一个连接基团或与相邻杂原子基团形成的任何连接基团要么保持稳定，要么降解，分子中的任何一个 PEG 段离散多分散或单分散。多功能聚乙二醇的支链结构和支臂长度灵活多样，各种参数和性能指标可调且易于控制，具有广泛的适用性。