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Merck

M4287

Sigma-Aldrich

丝裂霉素 C 来源于头状链霉菌

powder, suitable for cell culture, BioReagent

别名:

Mitomycin

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About This Item

经验公式(希尔记法):
C15H18N4O5
CAS号:
分子量:
334.33
Beilstein:
7231816
MDL编号:
UNSPSC代码:
12352207
PubChem化学物质编号:
NACRES:
NA.76
价格与库存信息目前不能提供

产品名称

丝裂霉素 C 来源于头状链霉菌, powder, BioReagent, suitable for cell culture

生物来源

Streptomyces caespitosus

质量水平

产品线

BioReagent

表单

powder

技术

cell culture | mammalian: suitable

颜色

gray
purple/blue

 

(1) 3.2, (2) 6.5

溶解性

H2O: 4 mL/vial, clear to slightly hazy, blue to purple (Stock solutions should be filter sterilized and stored at 2-8 °C in the dark.)

抗生素抗菌谱

Gram-negative bacteria
Gram-positive bacteria

作用机制

DNA synthesis | interferes

储存温度

2-8°C

SMILES字符串

[H][C@]12CN3C4=C([C@@H](COC(N)=O)[C@@]3(OC)[C@@]1([H])N2)C(=O)C(N)=C(C)C4=O

InChI

1S/C15H18N4O5/c1-5-9(16)12(21)8-6(4-24-14(17)22)15(23-2)13-7(18-13)3-19(15)10(8)11(5)20/h6-7,13,18H,3-4,16H2,1-2H3,(H2,17,22)/t6-,7+,13+,15-/m1/s1

InChI key

NWIBSHFKIJFRCO-WUDYKRTCSA-N

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一般描述

丝裂霉素C是全身性化疗化合物,是从 头状链霉菌中获得的抗生素。[1][2]它是鉴定的第一种生物还原性烷基化剂,是3-氨基-5-羟基苯甲酸(AHBA)、D-葡萄糖胺、L-蛋氨酸和氨甲酰基磷酸的衍生物。[3]
化学结构:氮丙啶

应用

头状链霉菌丝裂霉素C已用于处理饲养层,如PMEF(原代小鼠胚胎成纤维细胞)和CD1小鼠胚胎成纤维细胞(MEF),还用于培养人胚胎干细胞(hESC)。[4][5][6]它还用于处理BLC(基底样癌)细胞系。[7]

生化/生理作用

丝裂霉素C会引起DNA双链交联,导致诱变、抑制DNA合成、启动DNA修复事件和激活细胞凋亡。抑制DNA合成的作用归因于丝裂霉素C中存在的氨基醌基。[3][8]该化合物不影响RNA和蛋白质的合成。在组织培养中,该化合物降低细胞活力,抑制有丝分裂,导致细胞核解体和巨细胞产生。[2]丝裂霉素C具有强大的抗革兰氏阴性和革兰氏阳性菌活性。[8]它包含三个部分,分别为奎宁、氨基甲酸乙酯和氮丙啶。它可用于在细胞培养体系中产生有丝分裂失活的饲养细胞,例如胚胎干细胞体系中使用的有丝分裂失活的成纤维细胞。
作用机制:该产物是专门针对鸟嘌呤核苷序列5′-CpG-3′的烷基化剂。它通过与DNA共价反应,在DNA互补链之间形成交联来抑制DNA合成。 这种相互作用可防止DNA互补链分离,从而抑制DNA复制。

抗菌谱:丝裂霉素C具有很强的抗肿瘤活性,尤其是对艾氏腹水瘤细胞,对革兰氏阳性和革兰氏阴性细菌具有很强的杀菌作用。

注意

该小瓶包含2 mg丝裂霉素C和48 mg NaCl。 储备溶液应过滤灭菌,并在2-8℃避光储存。 pH 6-9的溶液可在0-5°C下储存一周,但如果形成沉淀,则应制备新溶液 - 已证实沉淀溶液对细胞有毒。

制备说明

丝裂霉素C可以0.5mg/mL溶于水,pH为6.0-7.5。 它在pH<6的酸性溶液中会迅速降解,在pH 6-9的溶液中最有可能保持活性。

相关产品

产品编号
说明
价格

象形图

Health hazardExclamation mark

警示用语:

Warning

危险声明

危险分类

Acute Tox. 4 Oral - Carc. 2

储存分类代码

13 - Non Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


历史批次信息供参考:

分析证书(COA)

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Mitomycin derivatives. 1. Preparation of mitosane and mitosene compounds and their biological activities.
S Kinoshita et al.
Journal of medicinal chemistry, 14(2), 103-109 (1971-02-01)
EFFECTS OF MITOMYCIN C ON HUMAN CHROMOSOMES.
M M COHEN et al.
The Journal of cell biology, 23, 386-395 (1964-11-01)
Akshay Gopinathan Nair et al.
Indian journal of ophthalmology, 63(4), 335-339 (2015-06-06)
Dacryocystorhinostomy (DCR) is the procedure of choice in patients with epiphora due to primary acquired nasolacrimal duct obstruction. The evolution of surgical tools, fiber-optic endoscopes, effective anesthesia techniques, and the adjunct use of antimetabolites intraoperatively; namely mitomycin-C (MMC) have significantly
Mavi Camarasa et al.
Cloning and stem cells, 11(3), 453-462 (2009-07-15)
Human embryonic stem cell (hESC) growth is dependent on various factors released by feeder cells. Some of them have already been elucidated, although much research is still needed to understand the biology of stem cell maintenance in culture. Traditionally, primary
Y Mao et al.
Chemistry & biology, 6(4), 251-263 (1999-04-01)
The mitomycins are natural products that contain a variety of functional groups, including aminobenzoquinone- and aziridine-ring systems. Mitomycin C (MC) was the first recognized bioreductive alkylating agent, and has been widely used clinically for antitumor therapy. Precursor-feeding studies showed that

商品

Antibiotic kill curve is a dose response experiment in which mammalian cells are subjected to increasing amounts of selection antibiotic

Antibiotic kill curve is a dose response experiment in which mammalian cells are subjected to increasing amounts of selection antibiotic

Antibiotic kill curve is a dose response experiment in which mammalian cells are subjected to increasing amounts of selection antibiotic

Antibiotic kill curve is a dose response experiment in which mammalian cells are subjected to increasing amounts of selection antibiotic

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实验方案

This technical article covers the indirect co-culture of embryonic stem cells with embryonic fibroblasts.

Questions

1–10 of 10 Questions  
  1. What is the main difference between M4287 and M0503? And are both of them suitable for cell culture?

    1 answer
    1. The main difference between M4287 and M0503 is that M4287 is specifically recommended for cell culture and is cell culture tested with a recommended concentration for use in eukaryotic cell culture.

      Helpful?

  2. Where can I find out the expiry date of the product (powder form, not dissolved yet)?

    1 answer
    1. This product is not assigned an expiration date. It is assigned a recommended retest date of approximately 4 years after the quality release date. A recommended retest date is the time during which the product is expected to remain within established stability specifications, provided that it has been stored under defined conditions. After the Retest Date, product samples should be examined to ensure that the product is still in compliance with the established specifications.

      For more information, you may access the "Product Dating Information" document under "ADDITIONAL USEFUL DOCUMENTS ABOUT OUR PRODUCTS" at the bottom of the Quality Services page with this link: https://www.sigmaaldrich.com/US/en/life-science/quality-and-regulatory-management/quality-services.

      Helpful?

  3. What concentration of Mitomycin C (Product M4287) for use with mesenchymal stem cells MSC?

    1 answer
    1. The use of Mitomycin C (Product M4287) with mesenchymal stem cells (MSC) has not been investigated. This is an application that will need to be validated by the end user.

      However, certain publications indicate the use of 1 mg/mL of mitomycin C stock solution in stromal cell culture.
      This concentration may be suitable: https://www.sciencedirect.com/science/article/pii/S0014483520304590

      Helpful?

  4. How long can it be stored at 4 degrees when dissolved in water? How should I store it to keep it active for a longer period of time?

    1 answer
    1. As mentioned in product information sheet, generally, solutions at pH 6–9 can be stored at 0–5 °C
      for up to a week. For more information please see https://www.sigmaaldrich.com/product/sigma/m4287

      Helpful?

  5. How should solutions of Mitomycin C, Product M4287, be stored?

    1 answer
    1. Solutions of this product should not be stored frozen. Solutions can be stored at 2-8°C, and should be used within 1-2 weeks. Solutions are light sensitive, but the powder is not.

      Helpful?

  6. At what concentration can Mitomycin C, Product M4287, be used with embryonic stem (ES) cells?

    1 answer
    1. Treatment of the feeder layer with media containing 100 micrograms/mL mitomycin at 37°C for 30 minutes blocked replication of ES cells.

      Helpful?

  7. What is the difference between Mitomycin C products M4287 and M0503?

    1 answer
    1. M4287 has been cell culture tested; M0503 has not been cell culture tested.

      Helpful?

  8. How should the product be dissolved?

    1 answer
    1. Mitomycin C is soluble at 0.5 mg/mL in water, yielding a clear blue solution.

      Helpful?

  9. What is the recommended concentration of Mitomycin C, Product M4287, should I use for eukaryote cell culture?

    1 answer
    1. A concentration between 10-50 micrograms/mL is typically used.

      Helpful?

  10. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

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