(+)-生物素胺己酰肼 | 109276-34-8

• 物质功能分类: 有机原料 - 肼或胲的有机衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 中文名称: (+)-生物素胺己酰肼
• 中文别名: (+)-生物素酰胺基己酸肼
• 英文名称: (5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-(6-hydrazinyl-6-oxohexyl)pentanamide)
• 英文别名: 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-(6-hydrazinyl-6-oxohexyl)pentanamide；N''-biotinyl-6-aminohexanoylhydrazide；N-biotinyl-6-amino-caproic hydrazide；biotinamidohexanoic acid hydrazide；6-biotinamidocaproylhydrazide；biotinamidocaproylhydrazide；Biotinamidocaproyl hydrazide
• CAS: 109276-34-8
• 化学式: C₁₆H₂₉N₅O₃S
• mdl: MFCD00077659
• 分子量: 371.504
• InChiKey: IJJWOSAXNHWBPR-HUBLWGQQSA-N

物化性质

• 熔点：
  195-196°C
• 沸点：
  777.0±55.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：25 毫克/毫升
• 稳定性/保质期：
  常温常压下稳定，避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.812
• 拓扑面积：
  151
• 氢给体数：
  5
• 氢受体数：
  5

安全信息

• WGK Germany：
  -
• 海关编码：
  29349990
• 安全说明：
  S22,S24/25
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封储存，应存放在阴凉干燥的库房中。冷藏时温度应保持在2-8°C。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : (+)-Biotinamidohexanoic acid hydrazide
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 109276-34-8

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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. This substance is not
classified as dangerous according to Directive 67/548/EEC.
Label elements
This substance is not classified as dangerous according to Directive 67/548/EEC.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : BACH
(+)-Biotin-ε-aminocaproyl hydrazide
(+)-Biotinamidocaproyl hydrazide
(+)-Biotin-X-hydrazide
N-(+)-Biotinyl-6-aminohexanoic hydrazide
Formula : C16H29N5O3S
Molecular Weight : 371,50 g/mol
CAS-No. : 109276-34-8
No components need to be disclosed according to the applicable regulations.

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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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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), Sulphur oxides
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.
For personal protection see section 8.
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.
For precautions see section 2.2.
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: 2 - 8 °C
Keep in a dry place.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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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).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 211 °C
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) Auto-ignition 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
Stable under recommended storage conditions.
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
In the event of fire: see section 5

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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
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Gastrointestinal disturbance, May cause convulsions., To the best of our knowledge, the chemical,
physical, and toxicological properties have not been thoroughly investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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.

---

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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

Biotin LC hydrazide 是一种长链蛋白修饰试剂，能够将高碘酸盐氧化的糖蛋白转化为特定结构。

体外研究

Biotin LC hydrazide（BACH）常用于靶向糖蛋白和糖基。它具有碳水化合物反应性，并且比普通的生物素羟醛缩合物更为敏感。此外，还开发了一种新的DNA生物标记系统，该系统使用 Biotin LC hydrazide（氨基己酰基生物素）和戊二醛进行操作。

反应信息

• 作为反应物：
  描述：

  (+)-脱落酸 、 (+)-生物素胺己酰肼 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Biotin-labeled abscisic acid as a probe for investigating abscisic acid binding sites on plasma membranes of barley aleurone protoplasts

  摘要：

  Plant hormone abscisic acid (ABA) plays important roles in dormancy and stress responses, but its binding sites have not yet been fully elucidated. In this report, we suggest the utility of biotin-labeled abscisic acid (bioABA) as a probe to investigate ABA-binding sites on the plasma membrane of barley aleurone protoplasts. BioABA was approximately 100 times less effective than ABA in inhibiting expression of gibberellin-inducible alpha-amylase and in inducing expression of a reporter gene fused to the dehydrin promoter. To ascertain that bioABA could bind to ABA-binding sites on the plasma membrane, we used fluorescence flow cytometry to measure the fluorescence intensity of aleurone protoplasts treated with a combination of bioABA and fluorescence-labeled streptavidin. Addition of bioABA increased the fluorescence of aleurone protoplasts in a concentration-dependent manner, but addition of non-active bioABA derivatives did not. Furthermore, the increase in fluorescence intensity observed upon addition of bioABA was eliminated by co-treatment with excess ABA, but it was not eliminated by co-treatment with other plant hormones. These results suggest that bioABA binds to ABA-binding sites, and that bioABA should be a valuable probe for investigating ABA-binding sites on the plasma membrane. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.017
• 作为产物：
  描述：

  (+)生物素-N-琥珀酰亚胺基酯 在 氯化亚砜 、 hydrazine hydrate 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 29.0h， 生成 (+)-生物素胺己酰肼
  参考文献：
  名称：

  用于探测Nur77蛋白诱导途径的生物素化强心苷的设计与合成。

  摘要：

  孤儿核受体Nur77（也称为TR3或神经生长因子诱导的克隆B NGFI-B）在调节靶基因表达中起核转录因子的作用，并且在分化，增殖，凋亡，和许多不同细胞类型的存活率 最近的研究表明，Nur77还涉及许多重要的生理和病理过程，包括癌症，炎症和免疫力，心血管疾病和骨骼疾病。我们以前的研究表明强心苷可以诱导Nur77蛋白的表达及其从细胞核到细胞质的转运，然后靶向线粒体，从而导致癌细胞凋亡。为了探测Nur77蛋白的诱导途径，我们设计并合成了一系列新型的生物素化的强心苷，它们分别来自β-安提香和α-安提香，这是两种来自安提阿里斯毒株的典型强心苷。评价了这些生物素化强心苷Nur77蛋白表达的诱导及其对NIH-H460癌细胞增殖的抑制作用。结果表明，一些生物素化的强心苷可以显着诱导Nur77蛋白的表达，与它们的母体化合物β-Antiarin和α-Antiarin相当。而且，评估了它们的抗生蛋白链菌素结合

  DOI：

  10.1016/j.bmcl.2019.01.015

文献信息

• Tailored Multivalent Neo-Glycoproteins: Synthesis, Evaluation, and Application of a Library of Galectin-3-Binding Glycan Ligands
  作者：Dominic Laaf、Pavla Bojarová、Helena Pelantová、Vladimír Křen、Lothar Elling

  DOI：10.1021/acs.bioconjchem.7b00520

  日期：2017.11.15

  albumin (BSA) was accomplished by dialkyl squarate coupling to lysine residues resulting in a library of defined multivalent neo-glycoproteins. Solid-phase binding assays with immobilized neo-glycoproteins revealed distinct affinity and specificity of the multivalent glycan epitopes for Gal-3 binding. In particular, neo-glycoproteins decorated with N′,N″-diacetyllactosamine (GalNAcβ1,4GlcNAc; LacdiNAc) epitopes

  Galectin-3（Gal-3）是β-半乳糖苷结合凝集素家族的成员，是一种肿瘤生物标志物，参与肿瘤血管生成和转移。因此，Gal-3被认为是早期癌症诊断和抗癌治疗的有希望的靶标。我们在这里提出了定制的多价新糖蛋白文库的合成，并评估了它们的Gal-3结合特性。通过结合使用糖基转移酶和化学酶促反应，我们首先合成了一组N-乙酰基乳糖胺（Galβ1,4GlcNAc； LacNAc 2型）为基础的寡糖，分别具有五个不同的终止糖基化表位。牛血清白蛋白（BSA）的新糖基化是通过将二烷基方酸与赖氨酸残基偶联而完成的，从而形成一个确定的多价新糖蛋白文库。固定化的新糖蛋白的固相结合测定显示了多价聚糖表位对Gal-3结合的独特亲和力和特异性。特别是，用N '，N修饰的新糖蛋白″-二乙酰基乳糖胺（GalNAcβ1,4GlcNAc; LacdiNAc）表位显示出高选择性，并被证明可以高亲和力从人血清中捕获Gal-3
• [EN] IDENTIFICATION OF COMPOUNDS WHICH INHIBIT ATG8-ATG3 PROTEIN-PROTEIN INTERACTION AND THEIR USE AS ANTIPARASITICAL AGENTS<br/>[FR] IDENTIFICATION DE COMPOSÉS QUI INHIBENT L'INTERACTION PROTÉINE-PROTÉINE ATG8-ATG3 ET LEUR UTILISATION COMME AGENTS ANTIPARASITAIRES
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2015164850A1

  公开（公告）日：2015-10-29

  The present invention provides compounds or a pharmaceutically acceptable salts, solvates, stereoisomers, or prodrugs thereof which can block the Atg8-Atg3 protein-protein interaction, which is associated with autophagy in apicomplexan organisms. Pharmaceutical compositions comprising these compounds and their use for the suppression and treatment of various parasitical diseases are also provided.

  本发明提供了一种可以阻断原始复合子生物体中与自噬有关的Atg8-Atg3蛋白-蛋白相互作用的化合物或其药用可接受的盐、溶剂合物、立体异构体或前药。还提供了包含这些化合物的药物组合物以及它们用于抑制和治疗各种寄生虫病的用途。
• Chemo-enzymatic modification of poly-<i>N</i>-acetyllactosamine (LacNAc) oligomers and <i>N,N</i>-diacetyllactosamine (LacDiNAc) based on galactose oxidase treatment
  作者：Christiane E Kupper、Ruben R Rosencrantz、Birgit Henßen、Helena Pelantová、Stephan Thönes、Anna Drozdová、Vladimir Křen、Lothar Elling

  DOI：10.3762/bjoc.8.80

  日期：——

  for studies of their possible therapeutic applications. We present the oxidation by galactose oxidase and subsequent chemical or enzymatic modification of terminal galactose and N-acetylgalactosamine residues of poly-N-acetyllactosamine (poly-LacNAc) oligomers and N,N-diacetyllactosamine (LacDiNAc) by galactose oxidase. Product formation starting from different poly-LacNAc oligomers was characterised

  聚糖在生物系统中的重要性因其在生理和病理过程中的各种功能而突出。糖蛋白和糖脂上的许多聚糖表位基于 N-乙酰乳糖胺单位 (LacNAc; Galbeta1,4GlcNAc)，并且经常存在于扩展的聚-LacNAc 聚糖 ([Galbeta1,4GlcNAc](n))。Poly-LacNAc 本身已被确定为半乳糖凝集素的结合基序，半乳糖凝集素是一类重要的凝集素，具有免疫反应和肿瘤发生的功能。因此，天然和修饰的聚-LacNAc 聚糖的合成对于与半乳糖凝集素的结合研究以及它们可能的治疗应用的研究具有特殊意义。我们介绍了半乳糖氧化酶的氧化作用以及随后的半乳糖氧化酶对聚 N-乙酰基乳糖胺 (poly-LacNAc) 寡聚体的末端半乳糖和 N-乙酰基半乳糖胺残基和 N,N-二乙酰基乳糖胺 (LacDiNAc) 的化学或酶促修饰。从不同的聚-LacNAc 低聚物开始的产品形成被表征和优化关于 C6-aldo
• Combination of UDP-Glc(NAc) 4′-Epimerase and Galactose Oxidase in a One-Pot Synthesis of Biotinylated Nucleotide Sugars
  作者：Darius-J. Namdjou、Birgit Sauerzapfe、Judith Schmiedel、Gerald Dräger、Stéphane Bernatchez、Warren W. Wakarchuk、Lothar Elling

  DOI：10.1002/adsc.200606169

  日期：2007.2.5

  Analysis by CE and NMR revealed a mixture (1.0:1.4) of the biotinylated nucleotide sugars uridine 5′-diphospho-6-biotin-ε-amidocaproylhydrazino-α-D-galactose (UDP-6-biotinyl-Gal, 7) and uridine 5′-diphospho-6-biotin-ε-amidocaproylhydrazino-α-D-glucose (UDP-6-biotinyl-Glc, 9), respectively, in a reaction started with 1. One product, uridine 5′-diphospho-6-biotin-ε-amidocaproylhydrazino-N-acetyl-α-D-galactosamine

  尿苷5'-二磷酸-α-D-葡萄糖（UDP-Glc，1）和尿苷5'-二磷酸-N-乙酰基-α-D-葡萄糖胺（UDP-GlcNAc，2）的酶促差向异构化将尿苷5'-二磷酸-α-D-半乳糖（UDP-Gal，3）和尿苷5'-二磷酸-N-乙酰基-α-D-半乳糖胺（UDP-GalNAc，4）与生物素-ε的化学生物素化结合一锅合成中的α-酰胺基丙烯酰肼。通过CE和NMR分析发现，生物素化核苷酸糖尿苷5'-二磷酸-6-生物素-ε-酰胺基丙烯酰肼基-α-D-半乳糖（UDP-6-生物素-Gal，7）的混合物（1.0：1.4 ）和尿苷5'-二磷酸-6-生物素-ε-酰胺基丙酰肼基-α-D-葡萄糖（UDP-6-生物素-Glc，9），分别从1开始。当用2引发反应时，形成了尿苷5'-二磷酸-6-生物素-ε-酰胺基丙酰肼基-N-乙酰基-α-D-半乳糖胺（UDP-6-生物素-GalNAc，8）。首次可以证明在酶催化中可以同时
• Custom-designed glycopolymer syntheses by terpolymerizations
  作者：Ren� Roy、Fran�ois D. Tropper、Anna Romanowska

  DOI：10.1039/c39920001611

  日期：——

  Carbohydrate derivatives having lectin binding properties and bearing N-acryloyl functionality have been copolymerized under three-component terpolymerization conditions with acrylamide and N-acryloylated effector molecules to provide water-soluble glycopolymers with custom designed physico-chemical properties.

  在三组份三元共聚条件下，具有凝集素结合特性和 N-丙烯酰官能团的碳水化合物衍生物与丙烯酰胺和 N-丙烯酰化效应分子进行了共聚，从而获得了具有定制理化特性的水溶性糖聚合物。