三赖氨酸 | 13184-14-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 赖氨酸类衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 三赖氨酸
• 中文别名: L-赖氨酰-L-赖氨酰-L-赖氨酸；赖酰氨-赖酰氨-赖氨酸
• 英文名称: Lys-Lys-Lys
• 英文别名: KKK；L-lysyl-L-lysyl-L-lysine；Trilysine；Lysyllysyllysine；(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2,6-diaminohexanoyl]amino]hexanoyl]amino]hexanoic acid
• CAS: 13184-14-0
• 化学式: C₁₈H₃₈N₆O₄
• 分子量: 402.538
• InChiKey: WBSCNDJQPKSPII-KKUMJFAQSA-N

物化性质

• 沸点：
  745.4±60.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  200
• 氢给体数：
  7
• 氢受体数：
  8

安全信息

• WGK Germany：
  3
• 海关编码：
  2924199090
• 储存条件：
  -20°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Lys-Lys-Lys
CAS-No. : 13184-14-0
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Trilysine
Formula : C18H38N6O4
Molecular Weight : 402,53 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: -20 °C
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
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. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
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. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

三赖氨酸来源于L-赖氨酸[1]。

反应信息

• 作为反应物：
  描述：

  三赖氨酸 在 nuclease P₁ 、 calcium chloride 、 维生素 B2 作用下， 以 水 为溶剂， 反应 96.5h， 生成
  参考文献：
  名称：

  Characterization of Lysine−Guanine Cross-Links upon One-Electron Oxidation of a Guanine-Containing Oligonucleotide in the Presence of a Trilysine Peptide

  摘要：

  Formation of DNA-protein cross-links involving the initial formation of a guanine radical cation was investigated. For this purpose, riboflavin-mediated photosensitization of a TGT oligonucleotide in aerated aqueous solution in the presence of the KKK tripeptide was performed. We have shown that the nucleophilic addition of the c-amino group of the central lysine residue of KKK to the C8 atom of either the guanine radical cation or its deprotonated form gives rise to the efficient formation of a N epsilon-(guanin-8-yl)-lysine cross-link. Interestingly, the time course of formation of the above-mentioned cross-link was found to be not linear with the time of irradiation, and its formation rapidly reached a plateau. This is explained by secondary decomposition of the initially generated cross-link which could be further oxidized more efficiently than starting TGT oligonucleotide. One-electron oxidation of the initially generated cross-link was found to produce mainly two diastereomeric cross-links exhibiting a spiroimino-trilysine-dihydantoin structure as inferred from enzymatic digestion, CD, UV, NMR and mass spectrometry measurements. In addition, other minor crosslinks, for which formation was favored at acidic pH, were assigned as lysine-guanine adducts in which the modified guanine base exhibits a guanidino-trilysine-iminohydantoin structure. A proposed mechanism for the formation of the different detected oligonucleotide-peptide cross-links is given. The high yield of formation of the detected cross-links strongly suggests that a DNA-protein cross-link involving a lysine residue linked to the C8 position of guanine could be generated in cellular systems if a lysine is located in the close vicinity of a guanine radical cation.

  DOI：

  10.1021/ja057656i
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 甲醇 、 palladium on activated charcoal 作用下， 生成 三赖氨酸
  参考文献：
  名称：

  95.赖氨酸的一些肽

  摘要：

  DOI：

  10.1039/jr9530000475
• 作为试剂：
  描述：

  titanium(IV) bis(ammonium lactato)dihydroxide 在 三赖氨酸 、 5-氯代水杨酸 作用下， 以 水 为溶剂， 生成 dioxide titanium
  参考文献：
  名称：

  Effect of peptide conformation on TiO2 biomineralization

  摘要：

  研究了富含赖氨酸的多肽对二氧化钛生物矿化的构象效应。多肽的生物矿化活性取决于氨基的空间接近程度，而这是由二级结构决定的。

  DOI：

  10.1039/c3dt51040a

文献信息

• [EN] DIPROVOCIMS: A NEW AND POTENT CLASS OF TLR AGONISTS<br/>[FR] DIPROVOCIMS: UNE NOUVELLE CLASSE PUISSANTE D'AGONISTES TLR
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2018005812A1

  公开（公告）日：2018-01-04

  A diprovocim compound that corresponds in structure to structural Formula V is disclosed, wherein A, W, Z, R1, R2, R3 and R4 (when present) are defined within. A diprovocim compound has immune-adjuvant properties on human and mouse cells in culture and on in vivo immunization of mice. A composition containing a diprovocim and a method of using a compound are also disclosed. The immunostimulatory activity of a diprovocim compound is similar to that of LPS, to which there is no apparent structural similarity. A contemplated compound bears no structural similarity to either the TLR1/TLR2 lipoprotein agonists nor to any other synthetic TLR agonist, and is remarkably easy to prepare and synthetically modify.

  揭示了一种与结构式V相对应的二丙醇化合物，其中A、W、Z、R1、R2、R3和R4（存在时）在内部定义。二丙醇化合物在培养的人类和小鼠细胞以及小鼠体内免疫接种中具有免疫佐剂特性。还揭示了含有二丙醇化合物的组合物和使用化合物的方法。二丙醇化合物的免疫刺激活性类似于脂多糖（LPS），但与之没有明显的结构相似性。所考虑的化合物与TLR1/TLR2脂蛋白激动剂或任何其他合成的TLR激动剂都没有结构相似性，并且非常容易制备和合成修饰。
• Modelling of prebiotic synthesis and selection of peptides under isothermal conditions and thermal cycling mode
  作者：O. V. Demina、A. S. Kononikhin、A. V. Laptev、A. A. Khodonov、E. N. Nikolaev、S. D. Varfolomeev

  DOI：10.1007/s11172-012-0060-3

  日期：2012.2

  The model peptide synthesis from mixtures of amino acids was carried out under the thermal cycling and isothermal modes. The compositions of the obtained mixtures of products and the primary amino acid sequence of the synthesized peptides were determined by Fourier transform ion cyclotron resonance mass spectrometry and tandem mass spectrometry in combination with high-performance liquid chromatography

  氨基酸混合物的模型肽合成在热循环和等温模式下进行。通过傅里叶变换离子回旋共振质谱和串联质谱结合高效液相色谱法，应用合成肽的从头测序，确定了所得产物混合物的组成和合成肽的一级氨基酸序列。产品。与可能的统计组相比，肽的天然合成过程显示在相对温和的温度条件下发生并且产生的肽数量显着减少。系统的演变发生在固相合成过程中，一系列最不稳定的肽消失了。
• Cascade polymer complexes, process for their production and pharmaceutical agents containing said complexes
  申请人：Schering AG

  公开号：US20020187101A1

  公开（公告）日：2002-12-12

  Cascade polymer complexes with at least 16 ions of an element of atomic numbers 20 to 29, 39, 42, 44 or 57-83, useful NMR or x-ray lymphography imaging.

  至少含有原子序数在20到29、39、42、44或57-83之间的元素离子16个的级联聚合物复合物，可用于核磁共振或X射线淋巴造影成像。
• Molecular Imaging of Cancer Cells In Vivo
  申请人：Morse David L.

  公开号：US20140161725A1

  公开（公告）日：2014-06-12

  Cellular targets on cancer cells have been identified that can be used with targeted molecular imaging to detect the cancer cells in vivo. Non-invasive methods for detecting cancer cells, such as metastasized cancer cells, are therefore provided. Also provided are compositions and kits for use in the disclosed methods.

  已经确定了可用于与靶向分子成像结合以在体内检测癌细胞的癌细胞细胞靶点。因此提供了用于检测癌细胞的非侵入性方法，例如转移性癌细胞。还提供了用于所述方法的组合物和试剂盒。
• Peptide-based targeted cancer therapeutics: Design, synthesis and biological evaluation
  作者：Iwan Iwanov、Arianna Rossi、Monica Montesi、Irini Doytchinova、Armen Sargsyan、Georgi Momekov、Silvia Panseri、Emilia Naydenova

  DOI：10.1016/j.ejps.2022.106249

  日期：2022.9

  synthesis (SPPS) by Fmoc (9-fluorenylmethoxycarbonyl) chemistry was used to synthesize target compounds. AutoDock Vina was applied for simulation binding to Abl. The biological activities were measured evaluating cytotoxic effect, induction of apoptosis and inhibition of cancer cells migration. The new peptides exhibited different concentration-dependent antiproliferative effect against the tumor cell lines

  癌症是与心血管疾病一起导致人类死亡的主要原因。Abl (Abelson) 酪氨酸激酶在转导控制多种癌症（如慢性髓性白血病 (CML)、乳腺癌和脑癌）的增殖、存活、迁移和侵袭的各种信号中发挥着重要作用。由于这些原因，Abl 酪氨酸激酶被认为是药物发现中的重要生物学靶标。在这项研究中，设计了一系列具有预期 Abl 抑制活性的基于赖氨酸的寡肽，类似于 FDA 批准的药物（即伊马替尼和尼罗替尼）的结合，合成，通过高效液相色谱 (HPLC) 纯化，通过质谱分析。 MS）和体外生物学测试在 CML（AR-230 和 K-562）、乳腺癌（MDA-MB 231 和 MDA-MB 468）和胶质母细胞瘤细胞系（U87 和 U118）中。通过 Fmoc (9-芴基甲氧羰基) 化学的固相肽合成 (SPPS) 用于合成目标化合物。AutoDock Vina 用于模拟绑定到 Abl。测量生物活性以评估细胞毒性作用