(2,5-二氧代吡咯烷-1-基)二苯基磷酸酯 | 75513-55-2

• 物质功能分类: 化学试剂 - 有机试剂 - 膦酸酯/膦酸盐
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2,5-二氧代吡咯烷-1-基)二苯基磷酸酯
• 中文别名: 二苯基N-琥珀酰亚胺磷酸酯
• 英文名称: N-succinimidyl diphenylphosphate
• 英文别名: SDPP；N-hydroxysuccinimido diphenyl phosphate；(2,5-Dioxopyrrolidin-1-yl) diphenyl phosphate
• CAS: 75513-55-2
• 化学式: C₁₆H₁₄NO₆P
• 分子量: 347.264
• InChiKey: BXMVKQIIJSXIBU-UHFFFAOYSA-N

物化性质

• 熔点：
  83-86 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

SDS

Version 1.2
Regulation (EC) No 1907/2006

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1 - Product and Company Information

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Product Name DIPHENYL SUCCINIMIDYL PHOSPHATE, 97%

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2 - Hazards Identification

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3 - Composition/Information on Ingredients

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Product Name CAS # EC no Annex I
Index Number
DIPHENYL SUCCINIMIDYL PHOSPHATE 75513-55-2 None None
Formula C16H14NO6P
Molecular Weight 347,2700 AMU

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4 - First Aid Measures

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AFTER INHALATION
If inhaled, remove to fresh air. If not breathing give
artificial respiration. If breathing is difficult, give oxygen.
AFTER SKIN CONTACT
In case of contact, immediately wash skin with soap and copious
amounts of water.
AFTER EYE CONTACT
In case of contact, immediately flush eyes with copious amounts
of water for at least 15 minutes.
AFTER INGESTION
If swallowed, wash out mouth with water provided person is
conscious. Call a physician.

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5 - Fire Fighting Measures

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EXTINGUISHING MEDIA
Suitable: Water spray. Carbon dioxide, dry chemical powder, or
appropriate foam.
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SPECIAL RISKS
Specific Hazard(s): Emits toxic fumes under fire conditions.
SPECIAL PROTECTIVE EQUIPMENT FOR FIREFIGHTERS
Wear self-contained breathing apparatus and protective clothing
to prevent contact with skin and eyes.

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6 - Accidental Release Measures

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PROCEDURE(S) OF PERSONAL PRECAUTION(S)
Wear respirator, chemical safety goggles, rubber boots, and
heavy rubber gloves.
METHODS FOR CLEANING UP
Sweep up, place in a bag and hold for waste disposal. Avoid
raising dust. Ventilate area and wash spill site after material
pickup is complete.

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7 - Handling and Storage

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HANDLING
Directions for Safe Handling: Avoid inhalation. Avoid contact
with eyes, skin, and clothing. Avoid prolonged or repeated
exposure.
STORAGE
Conditions of Storage: Keep tightly closed. Store in a cool dry
place.

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8 - Exposure Controls / Personal Protection

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ENGINEERING CONTROLS
Safety shower and eye bath. Mechanical exhaust required.
GENERAL HYGIENE MEASURES
Wash thoroughly after handling. Wash contaminated clothing before
reuse.
PERSONAL PROTECTIVE EQUIPMENT
Respiratory Protection: Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US)
or CEN (EU). Respiratory protection is not required. Where
protection from nuisance levels of dusts are desired, use type N95
(US) or type P1 (EN 143) dust masks.
Hand Protection: Compatible chemical-resistant gloves.
Eye Protection: Chemical safety goggles.

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9 - Physical and Chemical Properties

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Appearance Color: Faintly violet
Form: Powder
Property Value At Temperature or Pressure
pH N/A
BP/BP Range N/A
MP/MP Range 74,000 °C
Flash Point N/A
Flammability N/A
Autoignition Temp N/A
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Oxidizing Properties N/A
Explosive Properties N/A
Explosion Limits N/A
Vapor Pressure N/A
Partition Coefficient N/A
Viscosity N/A
Vapor Density N/A
Saturated Vapor Conc. N/A
Evaporation Rate N/A
Bulk Density N/A
Decomposition Temp. N/A
Solvent Content N/A
Water Content N/A
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A

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10 - Stability and Reactivity

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STABILITY
Materials to Avoid: Strong oxidizing agents.
HAZARDOUS DECOMPOSITION PRODUCTS
Hazardous Decomposition Products: Carbon monoxide, Carbon dioxide,
Thermal decomposition may produce toxic fumes of phosphorus oxides
and/or phosphine.

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11 - Toxicological Information

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SIGNS AND SYMPTOMS OF EXPOSURE
To the best of our knowledge, the chemical, physical, and
toxicological properties have not been thoroughly investigated.
ROUTE OF EXPOSURE
Skin Contact: May cause skin irritation.
Eye Contact: May cause eye irritation.
Multiple Routes: May be harmful by inhalation, ingestion, or
skin absorption.

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12 - Ecological Information

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No data available.

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13 - Disposal Considerations

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SUBSTANCE DISPOSAL
Dissolve or mix the material with a combustible solvent and burn
in a chemical incinerator equipped with an afterburner and
scrubber. Observe all federal, state, and local environmental
regulations.

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14 - Transport Information

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RID/ADR
Non-hazardous for road transport.
IMDG
Non-hazardous for sea transport.
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IATA
Non-hazardous for air transport.

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15 - Regulatory Information

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Caution: Substance not yet fully tested (EU).
COUNTRY SPECIFIC INFORMATION
Germany
WGK: 3
Self-Classification

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16 - Other Information

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WARRANTY
The above information is believed to be correct but does not
purport to be all inclusive and shall be used only as a guide. The
information in this document is based on the present state of our
knowledge and is applicable to the product with regard to
appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Inc.,
shall not be held liable for any damage resulting from handling or
from contact with the above product. See reverse side of invoice
or packing slip for additional terms and conditions of sale.
Copyright 2010 Co. License granted to make
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.
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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  苄氧羰基-L-丙氨酸 、 (2,5-二氧代吡咯烷-1-基)二苯基磷酸酯 在 三乙胺 作用下， 以87%的产率得到N-苄氧羰基-L-丙氨酸 N-羟基琥珀酰亚胺酯
  参考文献：
  名称：

  用于合成活性酯和肽的新型试剂（N_琥珀酰亚胺基二苯基磷酸酯）

  摘要：

  制备了N-琥珀酰亚胺基二苯基磷酸酯（SDPP）。该试剂可用于制备活性酯和肽，而不是二环己基碳二亚胺。

  DOI：

  10.1016/s0040-4039(00)92747-3
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 二苯基次膦酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2,5-二氧代吡咯烷-1-基)二苯基磷酸酯
  参考文献：
  名称：

  Self-assembled nanoparticles from hyaluronic acid–paclitaxel prodrugs for direct cytosolic delivery and enhanced antitumor activity

  摘要：

  A prodrug-based nanosystem obtained by formulating prodrug and nanotechnology into a system is one of the most promising strategies to enhance drug delivery for disease treatment. Herein, we report a new nanosystem based on HA-PTX conjugates (HA-PTX Ns), which penetrated across cell membranes into cytosol, thus enhancing paclitaxel (PTX) delivery. HA-PTX Ns were successfully obtained based on HA-PTX, and their average particle size was approximately 200 nm. Importantly, unlike other prodrug-based nanosystems, HA-PTX Ns obtained cellular entry without entrapment within the lysosomal-endosomal system by using pathways including clathrin-mediated endocytosis, microtubule-associated internalization, macropinocytosis and cholesterol-dependence. Due to significant accumulation in tumors, HA-PTX Ns had more than a 4-fold decrease in tumor volume on day 14 in contrast with PTX alone. In conclusion, HA-PTX Ns could enter cells, bypass the lysosomal-endosomal system and improve PTX delivery. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2015.07.069
• 作为试剂：
  描述：

  CBZ-L-缬氨酸 、 甘胺酸甲酯 在 (2,5-二氧代吡咯烷-1-基)二苯基磷酸酯 、 三乙胺 作用下， 生成 N-benzyloxycarbonylvalylglycine methyl ester
  参考文献：
  名称：

  用于合成活性酯和肽的新型试剂（N_琥珀酰亚胺基二苯基磷酸酯）

  摘要：

  制备了N-琥珀酰亚胺基二苯基磷酸酯（SDPP）。该试剂可用于制备活性酯和肽，而不是二环己基碳二亚胺。

  DOI：

  10.1016/s0040-4039(00)92747-3

文献信息

• [EN] BIOLOGICAL MATERIALS AND USES THEREOF<br/>[FR] MATÉRIELS BIOLOGIQUES ET LEURS UTILISATIONS
  申请人：ANTIKOR BIOPHARMA LTD

  公开号：WO2016046574A1

  公开（公告）日：2016-03-31

  The invention provides compounds comprising a therapeutic agent coupled to a carrier molecule, with a minimum coupling ratio of 5: 1; wherein the carrier molecule is (i) an antibody fragment or derivative thereof or (ii) an antibody mimetic or derivative thereof; and wherein the therapeutic agents are coupled onto a lysine amino acid residue; and further wherein the therapeutic agent is not a photosensitising agent. There is also provided uses, methods relating to such compounds, as well as processes for their manufacture.

  该发明提供了包含治疗剂与载体分子偶联的化合物，最低偶联比为5:1；其中，载体分子是(i)抗体片段或其衍生物，或(ii)抗体模拟物或其衍生物；治疗剂偶联到赖氨酸氨基酸残基上；进一步，治疗剂不是光敏剂。还提供了关于这些化合物的用途、方法以及其制造过程。
• PRODRUG COMPOSITIONS, PRODRUG NANOPARTICLES, AND METHODS OF USE THEREOF
  申请人：Washington University

  公开号：US20160279060A1

  公开（公告）日：2016-09-29

  The present invention encompasses prodrug compositions, nanoparticles comprising one or more prodrugs, and methods of use thereof.

  本发明涵盖了前药组合物、包含一种或多种前药的纳米粒子，以及其使用方法。
• Synthetic copolymer conjugates of docetaxel and<i>in vitro</i>assessment of anticancer efficacy
  作者：Cameron W. Evans、Sky Edwards、Jessica A. Kretzmann、Gareth L. Nealon、Ruhani Singh、Tristan D. Clemons、Marck Norret、Cyrille A. Boyer、K. Swaminathan Iyer

  DOI：10.1039/d0nj03425h

  日期：——

  Docetaxel (DTX) is a widely used chemotherapy drug that is associated with numerous side effects and limited bioavailability. We show synthetic copolymer conjugates of docetaxel with drug loading up to 20% and assess their efficacy in MCF-7 cells.

  紫杉醇（DTX）是一种广泛使用的化疗药物，与许多副作用和有限的生物利用度相关。我们展示了紫杉醇与合成共聚物结合物，药物载荷高达20％，并评估它们在MCF-7细胞中的有效性。
• Imido carbonate compound, production thereof and uses thereof as reagent
  申请人：Ogura; Haruo

  公开号：US04341707A1

  公开（公告）日：1982-07-27

  A new carbonate compound which is N,N'-di-succinimidyl carbonate, N,N'-diphthalimidyl carbonate or N,N'-bis(5-norbornene-2,3-dicarboxyimidyl) carbonate is produced by reacting an N-hydroxy compound of the formula R-OH wherein R is succinimido, phthalimido or 5-norbornene-2,3-dicarboximido group, with a silylating agent, followed by reacting the resultant silylated product with phosgene, or alternatively by reacting said N-hydroxy compound with trichloromethyl chloroformate either in the molten state or in the presence of a non-polar organic solvent such as xylene. This new carbonate compound is useful not only as a reagent for forming active esters from amino acid but also as a reagent for introducing a carbonyl group between a pair of amino groups, a pair of amino and hydroxyl groups or a pair of amino and mercapto groups, for producing an isothiocyanate from a dithicarbamic acid by removal of hydrogen sulfide from the latter, and for producing acrylic acid derivatives from N-protected serine by dehydration of the latter.

  通过将化合物R-OH（其中R是琥珀酰亚胺基团，邻苯二甲酰亚胺基团或5-去氢莫尔宁-2,3-二羧酰亚胺基团）与硅烷化剂反应，然后将所得的硅烷化产物与光气反应，或者通过将所述N-羟基化合物与三氯甲基氯甲酸酯在熔融状态下或在类似二甲苯的非极性有机溶剂的存在下反应，可以制备一种新的碳酸酯化合物，其为N，N'-二琥珀酰亚胺基碳酸酯，N，N'-二邻苯二甲酰亚胺基碳酸酯或N，N'-双（5-去氢莫尔宁-2,3-二羧酰亚胺基）碳酸酯。这种新的碳酸酯化合物不仅可用作从氨基酸形成活性酯的试剂，还可用作在一对氨基基团、一对氨基和羟基基团或一对氨基和巯基基团之间引入羰基基团的试剂，通过从后者中去除硫化氢从二硫代氨基甲酸生成异硫氰酸酯，以及通过从N-保护丝氨酸脱水生成丙烯酸衍生物的试剂。
• Design, Synthesis and Applications of Hyaluronic Acid-Paclitaxel Bioconjugates†
  作者：Francesca Leonelli、Angela La Bella、Luisa Migneco、Rinaldo Bettolo

  DOI：10.3390/molecules13020360

  日期：——

  Paclitaxel (1a), a well known antitumor agent adopted mainly for the treatmentof breast and ovarian cancer, suffers from significant disadvantages such as low solubility,certain toxicity and specific drug-resistance of some tumor cells. To overcome theseproblems extensive research has been carried out. Among the various proposed strategies,the conjugation of paclitaxel (1a) to a biocompatible polymer, such as hyaluronic acid(HA, 2), has also been considered. Coupling a bioactive compound to a biocompatiblepolymer offers, in general, many advantages such as better drug solubilization, betterstabilization, specific localization and controlled release. Hereafter the design, synthesisand applications of hyaluronic acid-paclitaxel bioconjugates are reviewed. An overview ofHA-paclitaxel combinations is also given.

  紫杉醇（1a）是一种众所周知的抗肿瘤药物，主要用于治疗乳腺癌和卵巢癌，但它也存在着明显的缺点，如溶解度低、有一定毒性和某些肿瘤细胞的特异性耐药性。为了克服这些问题，人们进行了广泛的研究。在提出的各种策略中，紫杉醇（1a）与生物相容性聚合物（如透明质酸（HA，2））的共轭也被考虑在内。一般来说，将生物活性化合物与生物相容性聚合物结合在一起具有许多优点，如更好的药物溶解性、更好的稳定性、特异性定位和可控释放。下面将对透明质酸-紫杉醇生物共轭物的设计、合成和应用进行综述。此外，还概述了透明质酸-紫杉醇的组合。