腺嘌呤黄素 | 146-14-5

• 物质功能分类: 生物化工 - 核酸类
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 黄素核苷酸
• 中文名称: 腺嘌呤黄素
• 中文别名: 腺嘌呤黄素二核苷酸；黄素腺嘌呤二核苷酸；氟-氨碇；核黄素-5'-腺苷二磷酸,RIBOFLAVIN-5'-ADENOSINE-DIPHOSPHATE；二核苷酸核黄素腺苷；二核苷酸黄素腺嘌呤；核黄素腺苷双核苷酸；黄素腺嘌呤二核苷酸钠
• 英文名称: flavin adenine dinucleotide
• 英文别名: FAD；flavine adenine dinucleotide；riboflavin 5' adenosine diphosphate；Flavitan；Adenine-flavine dinucleotide；[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] hydrogen phosphate
• CAS: 146-14-5
• 化学式: C₂₇H₃₃N₉O₁₅P₂
• 分子量: 785.558
• InChiKey: VWWQXMAJTJZDQX-UYBVJOGSSA-N

物化性质

• 密度：
  2.08±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于甲醇（轻微加热）、水（轻微）
• 物理描述：
  Solid
• 碰撞截面：
  247.3 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
• 稳定性/保质期：
  在常温常压下，该物质是稳定的。

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  53
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  356
• 氢给体数：
  9
• 氢受体数：
  20

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  29349990
• RTECS号：
  AU7470000
• 储存条件：
  在-20°C条件下保存。

SDS

Name:	Flavine-adenine dinucleotide, 96% (uv-vis) Material Safety Data Sheet
Synonym:	Adenine-riboflavin dinucleotide; Flavine Adenosine Diphosphate; Isoalloxazine-adenine dinucleotide; FAD.
CAS:	146-14-5

Section 1 - Chemical Product MSDS Name: Flavine-adenine dinucleotide, 96% (uv-vis) Material Safety Data Sheet
Synonym: Adenine-riboflavin dinucleotide; Flavine Adenosine Diphosphate; Isoalloxazine-adenine dinucleotide; FAD.

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
146-14-5	Flavine-adenine dinucleotide	96.0	205-663-1

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW The toxicological properties of this material have not been fully investigated. Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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SECTION 4 - FIRST AID MEASURES
Eyes:
Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Antidote: None reported.

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SECTION 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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SECTION 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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SECTION 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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SECTION 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 146-14-5: Personal Protective Equipment
Eyes:
Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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SECTION 9 - PHYSICAL AND CHEMICAL PROPERTIES
Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C27H31N9Na2O15P2
Molecular Weight: 829.1955

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SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
None reported.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of phosphorus, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Will not occur.

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 146-14-5: AU7470000
LD50/LC50:
CAS# 146-14-5: Oral, mouse: LD50 = >7 gm/kg.
Carcinogenicity:
Flavine-adenine dinucleotide - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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SECTION 12 - ECOLOGICAL INFORMATION Other No information available.

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SECTION 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations.

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SECTION 14 - TRANSPORT INFORMATION IATA Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material.

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SECTION 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases: S 24/25 Avoid contact with skin and eyes. S 28A After contact with skin, wash immediately with plenty of water. S 37 Wear suitable gloves. S 45 In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). WGK (Water Danger/Protection) CAS# 146-14-5: No information available. Canada CAS# 146-14-5 is listed on Canada's NDSL List. CAS# 146-14-5 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 146-14-5 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 1/06/1999 Revision #2 Date: 3/18/2003 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

黄素腺嘌呤二核苷酸（FAD），又称活性型维生素B2或核黄素-5'-腺苷二磷酸，是一种参与重要代谢反应的氧化还原辅酶。FAD比NAD和NADP更强的氧化剂，并能通过1个电子或2个电子途径被还原。它可用于标记多种蛋白质，包括黄嘌呤腺嘌呤氧化酶、核黄素激酶、肿瘤坏死因子受体1 NADPH氧化酶等。

生物活性

FAD 是一种重要的氧化还原辅因子和蛋白质的辅助基团，在代谢过程中参与多个关键的酶反应。

靶点

Human Endogenous Metabolite

体外研究

聚（黄素腺嘌呤二核苷酸，P-FAD）通过额外的聚合型红ox还原反应，作为NADH氧化的有效电催化剂。在pH值为7.4时，以0.00 V的操作电位运行下，P-FAD 的电化学速率常数为 1.8 ± 0.6×10^-3 cm/s，接近于NADH的传质常数水平。修饰有P-FAD的电极表现出显著提高的稳定性，并被认为是分析化学中最优越的NADH转换器。

体内研究

2 mg/kg剂量的FAD经静脉注射后，可以显著逆转氯丙嗪（CPZ）引起的室颤阈值降低。FAD也能够中和氯丙嗪对狗心脏线粒体的影响，在给药后的10分钟内，狗会出现短暂低血压，随后恢复到初始水平，并防止了氯丙嗪诱导的线粒体功能障碍。

化学性质

橙黄色粉末状物质，具有吸湿性，易溶于水而不溶于乙醇，其水溶液呈黄绿色荧光。遇碱分解为核黄素。

用途

适用于治疗皮肤和黏膜疾病、神经性耳鸣、脑动脉硬化、顽固性头痛、肝硬化、黄疸及其他肝脏疾病、眼疾及视网膜疾病等。快速静注可能导致短暂胸部不适。

反应信息

• 作为反应物：
  描述：

  腺嘌呤黄素 在 Na2 anchored onto OAE-SEPHADEX anion exchanger phosphate buffer 、 氢气 作用下， 反应 1.67h， 生成 [(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲基[[(2R,3S,4S)-5-(7,8-二甲基-2,4-二氧代-1,5-二氢苯并[g]蝶啶-10-基)-2,3,4-三羟基戊氧基]-羟基磷酰]磷酸氢酯
  参考文献：
  名称：

  Catalytic reduction of redox-active co-factors and proteins by dihydrogen with sephadex supported platinum clusters as catalysts

  摘要：

  铂碳基簇 [Pt15(CO)30]2– 锚定在 QAE-SEPHADEX 阴离子交换剂上，是一种有效的催化剂，用于还原黄素辅因子、脂肪酰胺脱氢酶和细胞色素 c 氧化酶。

  DOI：

  10.1039/cc9960000207
• 作为产物：
  描述：

  O^5'-benzyloxyphosphinoyl-O^2'_,O3'-isopropylidene-adenosine 在 N-氯代丁二酰亚胺 、 乙腈 作用下， 生成 腺嘌呤黄素
  参考文献：
  名称：

  Christie et al., Journal of the Chemical Society, 1954, p. 46,49

  摘要：

  DOI：
• 作为试剂：
  描述：

  山奈酚 在 氧气 、 NADP+ 、 腺嘌呤黄素 作用下， 生成 六羟黄酮/栎草亭
  参考文献：
  名称：

  Formation of UV-honey guides in Rudbeckia hirta

  摘要：

  The UV-honey guides of Rudbeckia hirta were investigated by UV-photography, reflectance spectroscopy, LC-MS analysis and studies of the enzymes involved in the formation of the W-absorbing flavonols present in the petals. It was shown for the first time that the typical bull's eye pattern is already established at the early stages of flower anthesis on the front side of the petal surface, but is hidden to pollinators until the buds are open and the petals are unfolded. The rear side of the petals remains W-reflecting during the whole flower anthesis. Studies on the local distribution of 19 flavonols across the petals confirmed that the majority are concentrated in the basal part of the ray flower. However, in contrast to the earlier studies, eupatolitin 3-O-glucoside (6,7-dimethoxyquercetin 3-O-glucoside) was present in both the basal and apical parts of the petals, whereas eupatolin (6,7-dimethoxyquercetin 3-O-rhamnoside) was exclusively found in the apical parts. The enzymes involved in the formation of the flavonols in R. hirta were demonstrated for the first time. These include a rare flavonol 6-hydroxylase, which was identified as cytochrome P450-dependent monooxygenase and did not accept any methylated flavonol as substrate. All enzymes were present in the basal and apical parts of the petals, although some of them clearly showed higher activities in the basal part. This indicates that the local accumulation of flavonols in R. hirta is not achieved by a locally restricted presence of the enzymes involved in flavonol formation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.04.017

文献信息

• Methylene Homologues of Artemisone: An Unexpected Structure-Activity Relationship and a Possible Implication for the Design of C10-Substituted Artemisinins
  作者：Yuet Wu、Ronald Wai Kung Wu、Kwan Wing Cheu、Ian D. Williams、Sanjeev Krishna、Ksenija Slavic、Andrew M. Gravett、Wai M. Liu、Ho Ning Wong、Richard K. Haynes

  DOI：10.1002/cmdc.201600011

  日期：2016.7.5

  may possess enhanced biological activities and stabilities. Dihydroartemisinin was converted into 10β‐cyano‐10‐deoxyartemisinin that was hydrolyzed to the α‐primary amide. Reduction of the β‐cyanide and the α‐amide provided the respective methylamine epimers that upon treatment with divinyl sulfone gave the β‐ and α‐methylene homologues, respectively, of artemisone. Surprisingly, the compounds were

  我们试图确定青蒿素的亚甲基同系物是否比青蒿素在生物学上更活泼，更稳定。通过将天然的O和N糖苷转化为可能具有增强的生物活性和稳定性的更稳定的C糖苷来进行类比。将双氢青蒿素转化为10β-氰基-10-脱氧青蒿素，然后将其水解为α-伯酰胺。β-氰化物和α-酰胺的还原提供了各自的甲胺差向异构体，二甲砜处理后分别得到了青蒿素的β-和α-亚甲基同系物。令人惊讶的是，该化合物在体外对恶性疟原虫的活性低于青蒿素。并且对A549，HCT116和MCF7肿瘤细胞系没有明显的活性。可以根据一种针对青蒿素的作用机理的模型，即辅因子模型，来合理化这种活性损失，其中，在细胞内扰动过程中，C10上存在一个离去基团有助于驱动氢化物从还原的黄素辅因子转移至过氧化物。青蒿素的氧化还原稳态。值得注意的是，蒿甲醚的碳水化合物类似物在体外对恶性疟原虫的活性低于邻糖苷母体。，尽管目前尚无法将此类活性差异外推至其他青蒿素。但是，文献数据
• Establishing the Kinetic Competency of the Cationic Imine Intermediate in Nitroalkane Oxidase
  作者：Michael P. Valley、Shane E. Tichy、Paul F. Fitzpatrick

  DOI：10.1021/ja043542f

  日期：2005.2.1

  effect of 7.9. These results are consistent with cyanide reacting with a species formed after proton abstraction but before flavin oxidation. The proposed mechanism for nitroalkane oxidase involves removal of a proton from the nitroalkane, forming a carbanion which adds to the flavin N(5). Elimination of nitrite from the resulting adduct would form an electrophilic imine which can be attacked by hydroxide

  黄素蛋白硝基烷氧化酶催化中性硝基烷氧化成相应的醛和酮。氰化物在转换过程中以浓度依赖性方式使酶失活。在硝基乙烷或硝基己烷的存在下，来自被氰化物灭活的酶的黄素的质谱分析表明已形成黄素氰乙基或氰己基中间体。在高浓度氰化物下，灭活不会消耗氧气。快速反应研究表明，与 2-(2H2)-硝基乙烷形成的加合物显示出 7.9 的动力学同位素效应。这些结果与氰化物与质子提取之后但黄素氧化之前形成的物质反应一致。硝基烷氧化酶的拟议机制包括从硝基烷中去除一个质子，形成添加到黄素 N(5) 的碳负离子。从所得加合物中消除亚硝酸盐会形成亲电亚胺，该亚胺可被氢氧化物攻击。目前的结果与氰化物捕获这种亲电子中间体一致。
• Photooxidation of 2′-deoxyguanosine 5′-monophosphate (dGMP) by flavin adenine dinucleotide (FAD) via electron transfer: a laser photolysis study
  作者：Chang-Yuan Lu、Si-De Yao、Nian-Yun Lin

  DOI：10.1016/s0009-2614(00)01092-7

  日期：2000.11

  The study of the photosensitization mechanism of dGMP by flavin adenine dinucleotide (FAD) as sensitizer was carried out by time-resolved 308 and 248 nm laser flash photolysis. Direct evidence of electron transfer from dGMP to either triplet state of FAD or oxidized FAD radical (FAD+/FAD(−H)) was obtained. A comparison of nucleotide-free and -bound riboflavin suggests that the nucleotide environment

  通过时间分辨的308和248 nm激光闪光光解法研究了以黄素腺嘌呤二核苷酸（FAD）为敏化剂的dGMP的光敏机理。电子从dGMP转移到FAD的三重态或氧化的FAD自由基的直接证据（FAD + / FAD（-H））。无核苷酸和结合核黄素的比较表明，核苷酸环境不会显着影响敏化剂的反应性。
• VITAMIN COMPRISING PYROLOQUINOLINE QUINONE AND USE THEREOF
  申请人：RIKEN

  公开号：EP1588709A1

  公开（公告）日：2005-10-26

  It is an object of the present invention to clarify the biochemical role of pyrroloquinoline quinone (PQQ) in living bodies by identifying an enzyme that uses PQQ as a coenzyme in mammals and then by clarifying the oxidation-reduction reaction, with which PQQ is associated as a coenzyme in living bodies. The present invention provides a method of using pyrroloquinoline quinone as a coenzyme for 2-aminoadipate 6-semialdehyde dehydrogenase.

  本发明的目的是通过鉴定在哺乳动物中使用吡咯喹啉喹醌（PQQ）作为辅酶的酶，然后通过澄清PQQ作为辅酶与氧化还原反应相关联的方式，来澄清PQQ在生物体内的生化作用。本发明提供了一种利用吡咯喹啉喹醌作为2-氨基己二酸6-半醛脱氢酶的辅酶的方法。
• Reactions of Antimalarial Peroxides with Each of Leucomethylene Blue and Dihydroflavins: Flavin Reductase and the Cofactor Model Exemplified
  作者：Richard K. Haynes、Kwan-Wing Cheu、Maggie Mei-Ki Tang、Min-Jiao Chen、Zu-Feng Guo、Zhi-Hong Guo、Paolo Coghi、Diego Monti

  DOI：10.1002/cmdc.201000508

  日期：2011.2.7

  argon. Under the same conditions, FADH2 in turn cleanly reduces the antimalarial drug methylene blue (MB) to leucomethylene blue. The latter is rapidly re‐oxidized by artemisinins, thus supporting the proposal that MB exerts its antimalarial activity, and synergizes the antimalarial action of artemisinins, by interfering with redox cycling involving NADPH reduction of flavin cofactors in parasite flavin

  在氩气中，pH 7.4的水性缓冲液中的NADPH-大肠杆菌黄素还原酶（Fre）将黄素腺嘌呤二核苷酸（FAD）还原为FADH 2。在相同条件下，FADH 2依次将抗疟疾药物亚甲基蓝（MB）还原为无色亚乙基蓝。后者被青蒿素迅速重新氧化，从而支持了MB发挥其抗疟活性，并通过干扰寄生虫黄素二硫键还原酶中黄素辅因子的NADPH还原的氧化还原循环，发挥了青蒿素的抗疟作用的提议。直接处理FADH 2在生理条件下，pH 7.4时，青蒿素和抗疟疾活性四恶烷和三恶烷结构类似物从NADPH-Fre-FAD中产生，导致青蒿素快速还原，过氧化物结构类似物有效转化为酮产物。FADH 2氧化相对速率的比较表明三氧戊环的最佳活性。因此，对于三氧戊环而言，寄生内氧化还原扰动的速率将最大，这与其增强的体外抗疟活性有关可能是重要的。使用BNAH-核黄素（RF）模型系统的1 H NMR光谱研究表明，四恶烷能够同时使用两个过氧化物单元来氧化RFH