N-乙酰基-酪氨酰-缬氨酰-丙氨酰-天冬氨酸-7-氨基-4-甲基香豆素 | 149231-65-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 天冬氨酸类衍生物
• 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: N-乙酰基-酪氨酰-缬氨酰-丙氨酰-天冬氨酸-7-氨基-4-甲基香豆素
• 中文别名: 蛋白酶1底物2m.荧光
• 英文名称: acetyl-YVAD-aminomethyl coumarine
• 英文别名: Ac-Tyr-Val-Ala-Asp-MCA；Ac-YVAD-AMC；3-[2-[[2-[[2-Acetamido-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]amino]propanoylamino]-4-[(4-methyl-2-oxochromen-7-yl)amino]-4-oxobutanoic acid；(3S)-3-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]amino]propanoyl]amino]-4-[(4-methyl-2-oxochromen-7-yl)amino]-4-oxobutanoic acid
• CAS: 149231-65-2
• 化学式: C₃₃H₃₉N₅O₁₀
• 分子量: 665.7
• InChiKey: YGLOALWHJIANIH-PQTMRPCPSA-N

物化性质

• 溶解度：
  在DMSO中的溶解度为10 mM如果没有水存在，该溶液在−20°C下在黑暗中稳定1个月以上。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  229
• 氢给体数：
  7
• 氢受体数：
  10

安全信息

• WGK Germany：
  3

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : N-Acetyl-Tyr-Val-Ala-Asp-7-amido-4-
methylcoumarin
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. : 149231-65-2

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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 : Ac-YVAD-AMC
Formula : C33H39N5O10
Molecular Weight : 665,69 g/mol
CAS-No. : 149231-65-2
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)
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 vapours, 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: -20 °C
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
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) Evapouration 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 sensitisation
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.

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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.

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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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-乙酰基-酪氨酰-缬氨酰-丙氨酰-天冬氨酸-7-氨基-4-甲基香豆素 在 recombinant human caspase-1 作用下， 以 二甲基亚砜 为溶剂， 生成 7-氨基-4-甲基香豆素
  参考文献：
  名称：

  Organic Azide Inhibitors of Cysteine Proteases

  摘要：

  Cysteine proteases are crucial regulatory enzymes in human physiology and disease. Inhibitors are usually designed with reactive electrophiles to covalently bond to the catalytic cysteinyl sulfur, and consequently they also indiscriminately interact with biological thiolates and other nucleophiles, leading to toxic side effects in vivo. Here we describe an alternative to using reactive electrophiles, demonstrating the use of a much less reactive azidomethylene substituent (-CH2-N3) that confers potent inhibition of cysteine proteases. This new approach resulted in potent, reversible, competitive inhibitors of caspase-1 (IC50 < 10 nM), with significant advantages over aldehydes such as high stability in vitro to thiols (10 mM dithiothreitol (pH 7.2), 20 mM glutathione (pH 7.2, 9, 11)) and aqueous media, as well as some highly desirable druglike features. It was also demonstrated that azides can be incorporated into inhibitors of other caspases (e.g. 3, 8) and cathepsins (e.g. K, S, B), indicating the versatility of this valuable new approach to cysteine protease inhibition.

  DOI：

  10.1021/ja0637649
• 作为产物：
  描述：

  Ac-Tyr(OBzl)-Val-Ala-Asp(OBzl)-MCA 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以89.3%的产率得到N-乙酰基-酪氨酰-缬氨酰-丙氨酰-天冬氨酸-7-氨基-4-甲基香豆素
  参考文献：
  名称：

  氨基酸和多肽。加大码 使用新开发的乙酰化试剂合成Ac-Tyr-Val-Ala-Asp-MCA。

  摘要：

  通过对H-Phe-Leu-CH2Cl进行环化，然后用乙酸酐进行乙酰化，制得2-乙酰氧基-3-苄基-5-甲基-6-异丁基吡嗪。该吡嗪衍生物可以与氨基酸或肽的氨基反应以产生乙酰基氨基酸或乙酰基肽，而不会使Tyr，Ser和Thr的羟基乙酰化。使用该乙酰化试剂，制备了白介素I（IL-1）加工酶的特异性底物Ac-Tyr-Val-Ala-Asp-MCA。

  DOI：

  10.1248/cpb.43.1336

文献信息

• [EN] INTERLEUKIN CONVERTING ENZYME AND APOPTOSIS<br/>[FR] ENZYME DE CONVERSION D'INTERLEUKINES ET APOPTOSE
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：WO1997007805A1

  公开（公告）日：1997-03-06

  (EN) The present invention is to the novel compounds of Formula (I), their pharmaceutical compositions, and to the novel inhibition of ICE and ICE-like proteins for use in the treatment of apoptosis, and disease states caused by excessive or inappropriate cell death.(FR) L'invention concerne des composés nouveaux de formule (I), leurs compositions pharmaceutiques et une inhibition nouvelle de protéines de l'enzyme de conversion d'interleukines et de protéines analogues à l'enzyme de conversion d'interleukines destinées à être utilisées pour traiter l'apoptose et les états pathologiques causés par une mort cellulaire excessive ou inappropriée.

  该发明涉及化合物式(I)的新型化合物、它们的药物组合物以及用于治疗由过度或不适当的细胞死亡引起的凋亡和疾病状态的新型ICE和类ICE蛋白的抑制。
• Methods for treating pulmonary fibrosis
  申请人：——

  公开号：US20030113330A1

  公开（公告）日：2003-06-19

  The present invention relates to uses of non-thiol ACE inhibitors, angiotensin II antagonists, angiotensin II receptor antagonists, endonuclease inhibitors, and caspase-inhibitors to treat pulmonary fibrosis and/or inhibit pulmonary epithelial cell apoptosis, including pulmonary fibrosis associated with amiodarone product toxicity.

  本发明涉及非硫醇 ACE 抑制剂、血管紧张素 II 拮抗剂、血管紧张素 II 受体拮抗剂、内切酶抑制剂和卡巴酶抑制剂治疗肺纤维化和/或抑制肺上皮细胞凋亡的用途，包括与胺碘酮产品毒性相关的肺纤维化。
• A substrate combinatorial array for caspases
  作者：Dennis Lee、Jerry L Adams、Martin Brandt、Walter E DeWolf、Paul M Keller、Mark A Levy

  DOI：10.1016/s0960-894x(99)00260-7

  日期：1999.6

  An efficient strategy for the synthesis of a tetrapeptidyl substrate combinatorial array directed toward the caspases is described. Testing of this array with caspases 1 and 4 gave substrate hydrolytic profiles characteristic of each caspase, and permitted the identification of efficiently processed substrates. A comparison of this approach to that using a positional scanning library is presented. (C) 1999 Elsevier Science Ltd. All rights reserved.
• INTERLEUKIN CONVERTING ENZYME AND APOPTOSIS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0851760A1

  公开（公告）日：1998-07-08
• EP0851760A4
  申请人：——

  公开号：EP0851760A4

  公开（公告）日：1998-11-25