MNNG

• メチルニトロニトロソグアニジン

関

methylnitronitrosoguanidine、N-methyl-N'-nitro-N-nitrosoguanidine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/22 06:23:44」(JST)

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Methylnitronitrosoguanidine

Names
IUPAC name 1-methyl-3-nitro-1-nitrosoguanidine
Other names N-Methyl-N-nitroso-N′-nitroguanidine; N-Methyl-N′-nitro-N-nitrosoguanidine
Identifiers
CAS Number	70-25-7 Y
Abbreviations	MNNG
ChemSpider	6025 N
Jmol 3D model	Interactive image
KEGG	C14592 Y
PubChem	6261
InChI InChI=1S/C2H5N5O3/c1-6(5-8)2(3)4-7(9)10/h1H3,(H2,3,4) N Key: VZUNGTLZRAYYDE-UHFFFAOYSA-N N InChI=1/C2H5N5O3/c1-6(5-8)2(3)4-7(9)10/h1H3,(H2,3,4) Key: VZUNGTLZRAYYDE-UHFFFAOYAT
SMILES CN(C(=N[N+](=O)[O-])N)N=O
Properties
Chemical formula	C2H5N5O3
Molar mass	147.09 g/mol
Appearance	Yellow crystals
Melting point	118 °C (244 °F; 391 K) (decomposes)
Solubility in water	reacts violently, slowly hydrolysed
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Methylnitronitrosoguanidine (MNNG or MNG) is a biochemical tool used experimentally as a carcinogen and mutagen. It acts by adding alkyl groups to the O⁶ of guanine and O⁴ of thymine, which can lead to transition mutations between GC and AT. These changes do not cause a heavy distortion in the double helix of DNA and thus are hard to detect by the DNA mismatch repair system.

In organic chemistry, MNNG is used as a source of diazomethane when reacted with aqueous potassium hydroxide.

MNNG is a probable human carcinogen listed as an IARC Group 2A carcinogen.

References

English Journal

• Synergistic effect of JQ1 and rapamycin for treatment of human osteosarcoma.

• Lee DH1, Qi J, Bradner JE, Said JW, Doan NB, Forscher C, Yang H, Koeffler HP.
• International journal of cancer. Journal international du cancer.Int J Cancer.2015 May 1;136(9):2055-64. doi: 10.1002/ijc.29269. Epub 2014 Oct 30.
• Bromodomain and extra terminal domain (BET) proteins are important epigenetic regulators facilitating the transcription of genes in chromatin areas linked to acetylated histones. JQ1, a BET protein inhibitor, has antiproliferative activity against many cancers, mainly through inhibition of c-MYC and
• PMID 25307878

• The bacterial alkyltransferase-like (eATL) protein protects mammalian cells against methylating agent-induced toxicity.

• Tomaszowski KH1, Aasland D1, Margison GP2, Williams E2, Pinder SI2, Modesti M3, Fuchs RP3, Kaina B4.
• DNA repair.DNA Repair (Amst).2015 Apr;28:14-20. doi: 10.1016/j.dnarep.2015.01.009. Epub 2015 Jan 31.
• In both pro- and eukaryotes, the mutagenic and toxic DNA adduct O(6)-methylguanine (O(6)MeG) is subject to repair by alkyltransferase proteins via methyl group transfer. In addition, in prokaryotes, there are proteins with sequence homology to alkyltransferases, collectively designated as alkyltrans
• PMID 25703834

• Mismatch repair-dependent metabolism of O(6)-methylguanine-containing DNA in Xenopus laevis egg extracts.

• Olivera Harris M1, Kallenberger L2, Artola Borán M2, Enoiu M2, Costanzo V3, Jiricny J4.
• DNA repair.DNA Repair (Amst).2015 Apr;28:1-7. doi: 10.1016/j.dnarep.2015.01.014. Epub 2015 Feb 4.
• The cytotoxicity of SN1-type alkylating agents such as N-methyl-N'-nitrosourea (MNU), N-methyl-N'-nitro-N-nitrosoguanidine (MNNG), or the cancer chemotherapeutics temozolomide, dacarbazine and streptozotocin has been ascribed to the persistence of O(6)-methylguanine ((me)G) in genomic DNA. One hypot
• PMID 25697728

Japanese Journal

• 麹菌の育種によるみその品質向上を目指して

• 戸井田 仁一
• 日本食品科学工学会誌 61(6), 213-217, 2014
• … We selected mutants generated by MNNG treatment of koji molds, and obtained two kinds of applicable strains for miso production. …
• NAID 130004678785

• アミトロール抵抗性大腸菌株におけるタンパク質発現解析

• 山口 安亮,宮野 百代,京極 仁美,山口 綾野,青木 拓,佐藤 高則,Yamaguchi Yasuaki,Miyano-Ono Momoyo,Kyogoku-Tsujinaka Hitomi,Yamaguchi Ayano,Aoki Taku,Satoh Takanori
• 徳島大学総合科学部自然科学研究 = Natural Science Research, The University of Tokushima 27(4), 81-88, 2013-10
• … In order to elucidate the mechanism on the AT-resistance in E.coli, we prepared the E.coli mutant strain by treating with chemical mutagen, MNNG, and then selected the AT-resistant E. …
• NAID 120005352783

• Dual Programmed Cell Death Pathways Induced by p53 Transactivation Overcome Resistance to Oncolytic Adenovirus in Human Osteosarcoma Cells

• Hasei Joe,Sasaki Tsuyoshi,Tazawa Hiroshi,Osaki Shuhei,Yamakawa Yasuaki,Kunisada Toshiyuki,Yoshida Aki,Hashimoto Yuuri,Onishi Teppei,Uno Futoshi,Kagawa Shunsuke,Urata Yasuo,Ozaki Toshifumi,Fujiwara Toshiyoshi
• Molecular Cancer Therapeutics 12(3), 314-325, 2013-03
• … The cytopathic activity of OBP-702 was examined in OBP-301-sensitive (U2OS and HOS) and OBP-301-resistant (SaOS-2 and MNNG/HOS) human osteosarcoma cells. … The antitumor effect of OBP-702 was further assessed using an orthotopic OBP-301-resistant MNNG/HOS osteosarcoma xenograft tumor model. … Moreover, OBP-702 suppressed tumor growth in an orthotopic OBP-301-resistant MNNG/HOS xenograft tumor model. …
• NAID 120005324798

Related Links

• 発がん性ニトロソ化合物の染色体異常誘発能に対するビールの影響

考 察 MNNG，MNU等のメチル化剤は，中性溶液中で非酵素的に求電子性のメチルカチオンにまで分解し，これが核酸塩 基の求核部位から攻撃されて塩基のメチル化を引き起こしDNAを損傷する。このDNA損傷が原因となり，遺伝子突

• scientist：杉村 隆 - JT生命誌研究館

微生物に突然変異を起こすことで知られていたニトロソグアニジン（MNNG）も、4NQOと同じ理屈で、発がん作用があるのではないかとねらいをつけた。しかし、ラットへの皮下注射を繰り返したが結果がなかなか出ない。もうやめようと ...

Related Pictures

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★リンクテーブル★

リンク元	「N-methyl-N'-nitro-N-nitrosoguanidine」「メチルニトロニトロソグアニジン」「methylnitronitrosoguanidine」
関連記事	「MN」

「N-methyl-N'-nitro-N-nitrosoguanidine」

　　[★]

N-メチル-N'-ニトロ-N-ニトロソグアニジン、メチルニトロニトロソグアニジン

関

methylnitronitrosoguanidine、MNNG

「メチルニトロニトロソグアニジン」

　　[★]

英

N-methyl-N'-nitro-N-nitrosoguanidine、methylnitronitrosoguanidine、MNNG

関

N-メチル-N'-ニトロ-N-ニトロソグアニジン

「methylnitronitrosoguanidine」

　　[★]

メチルニトロニトロソグアニジン

関

MNNG、N-methyl-N'-nitro-N-nitrosoguanidine

「MN」

　　[★] 膜性腎症 membranous nephropathy