Zinc(II) 3,3'-(3,8,13,17-tetramethyl-7,12-divinylporphyrin-2,18-diyl)dipropionate | 15442-64-5

• 物质功能分类: 有机原料 - 氨基化合物 - 磺酸类氨基化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: Zinc(II) 3,3'-(3,8,13,17-tetramethyl-7,12-divinylporphyrin-2,18-diyl)dipropionate
• 英文别名: zinc;3-[18-(2-carboxylatoethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoate
• CAS: 15442-64-5
• 化学式: C34H32N4O4Zn
• 分子量: 626.0
• InChiKey: AAHFFMFJYIWDLV-UHFFFAOYSA-L

物化性质

• 溶解度：
  DMSO：50 mg/mL（79.87 mM；需要超声波）H2O：< 0.1 mg/mL（不溶）
• 稳定性/保质期：
  在常温常压下稳定，需避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• TSCA：
  Yes
• WGK Germany：
  3

SDS

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Section 1: Product Identification
Chemical Name: Zinc protoporphyrin
CAS Registry Number: 15442-64-5
Formula: (C34H32N4O4)Zn
EINECS Number: 239-455-7
Chemical Family: metal porphine (porphyrin) complex
Synonym: protoporphoryn zinc chelate

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 15442-64-5 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Dust may be irritating to skin, eyes and mucous membranes. May be harmful if swallowed.
Primary Routes of Exposure: Ingestion, inhalation
Eye Contact: May cause slight to mild irritation of the eyes.
Skin Contact: May cause slight to mild irritation of the skin.
Inhalation: Some zinc containing dusts irritate the respiratory system and cause metallic taste, dry throat, and chills.
Ingestion: If solubilized, Zinc compounds give a harsh metallic taste and may cause nausea and vomiting.
Acute Health Affects: May be irritating to skin, eyes and respiratory tract. Inhalation may cause chills and nausea.
No serious long-term chronic effects associated with zinc compounds. Prolonged inhalation may cause
Chronic Health Affects:
laryngitis. Prolonged ingestion may cause constipation.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: not applicable
Autoignition Temperature: none
Explosion Limits: none
Extinguishing Medium: carbon dioxide, foam or dry powder
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self- contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit toxic and corrosive fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite, sodium carbonate or other suitable non combustible adsorbent and
Spill and Leak Procedures:
swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store in a cool, dry place in a tightly sealed container.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Material may form a fine dust. If possible, handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Material may form a fine dust. If possible, handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: purple xtl.
Molecular Weight: 626.03
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: Insoluble

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SECTION 10: Stability and Reactivity
Stability: air and moisture stable
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: Oxidizing agents
Decomposition Products: zinc oxide, nitrogen oxides, carbon monoxide, carbon dioxide and organic fumes.

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: No data
Mutagenic Effects: No data
Tetratogenic Effects: No data

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SECTION 12: Ecological Information
Ecological Information: Avoid release to the environment. Very toxic to aquatic organisms.

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SECTION 13: Disposal Considerations
This material and its container must be disposed of as hazardous waste according to local, state and federal
Disposal:
regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Listed in the TSCA inventory.
SARA (Title 313): Title compound: See category N982 for reporting.
Second Ingredient: None

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

Zinc Protoporphyrin (Zn(II)-protoporphyrin IX) 是一种具有口服活性的、竞争性的血红素加氧酶-1 (HO-1) 抑制剂，显著减弱间苯三酚 (PG) 对 H2O2 的保护作用。Zinc Protoporphyrin 可用作个体孕妇和儿童缺铁的筛查标志物，并用于评估人群铁状态与血红蛋白浓度的组合。此外，它具有抗癌活性。

靶点

Human Endogenous Metabolite

体外研究

锌原卟啉 (Zn(II)-protoporphyrin IX) 在 5 μM 浓度下处理 72 小时后，使晚期凋亡和坏死细胞的比例从对照组的 10.9% 增加到 30.4%。在 1.25-40 μM 浓度下处理 48 或 72 小时后，锌原卟啉对肿瘤细胞表现出抗增殖/毒性作用。在 2.5、5 μM 浓度下处理 48 或 72 小时时，锌原卟啉导致 G1 期细胞数量的剂量和时间依赖性减少。在 1.25-40 μM 浓度下处理 48 小时后，锌原卟啉诱导裂解 (活性) 胰凝乳蛋白酶-3 的积累。

凋亡分析

• 细胞系：C-26 细胞
• 浓度：5 μM
• 培养时间：72 小时
• 结果：晚期凋亡和坏死细胞的比例从对照组的 10.9% 增加到处理后的 30.4%。

细胞毒性测定

• 细胞系：C-26 细胞 和 MDA-MB231 细胞
• 浓度：1.25, 2.5, 5, 10, 20, 40 μM
• 培养时间：48 或 72 小时
• 结果：对肿瘤细胞表现出抗增殖/毒性作用。

细胞周期分析

• 细胞系：C-26 细胞
• 浓度：2.5, 5 μM
• 培养时间：48 或 72 小时
• 结果：导致 G1 期细胞数量的剂量和时间依赖性减少。

Western Blot 分析

• 细胞系：C-26 细胞
• 浓度：1.25, 2.5, 5, 10, 20, 40 μM
• 培养时间：48 小时
• 结果：诱导裂解 (活性) 胰凝乳蛋白酶-3 的积累。

体内研究

在 BALB/c 小鼠接种 C-26 细胞后，采用腹腔注射（i.p.）12.5, 25, 50 mg/kg 或口服（p.o.）12.5, 50 mg/kg (从第7天到第19天)，锌原卟啉表现出剂量依赖性抗肿瘤作用，并表现为肿瘤生长的延缓。

结果

腹腔注射或口服；从第7天到第19天

• 结果：表现出剂量依赖性的抗肿瘤作用，表现在肿瘤生长的延迟。