1H-Pyrrole-2-carboxamide,N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl]-4-[[[4-(formylamino)-1-methyl-1H-pyrrol-2-yl]carbonyl]amino]-1-methyl-

Names

[ CAS No. ]:
636-47-5

[ Name ]:
1H-Pyrrole-2-carboxamide,N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl]-4-[[[4-(formylamino)-1-methyl-1H-pyrrol-2-yl]carbonyl]amino]-1-methyl-

[Synonym ]:
stallimycin
Distamycin-3
Distamycin

Biological Activity

[Description]:

Distamycin A (NSC-82150), an oligopeptide antibiotic, is a minor groove binder which binds to B-form DNA, preferentially at A/T rich sites.Distamycin A can change Enediyne-induced DNA cleavage sites and enhances apoptosis[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Infection

[In Vitro]

Distamycin A 与 DNA 结合，通过伸直螺旋轴并将其延长近 12-15% 来加宽小沟[2]。 Distamycin A 增强 5'-CCT-3'/3'-GGA-5' 和 5'-CCA-3'/3'-GGT-5' 序列的双链 DNA 切割[3]< /sup>. Distamycin A 在 HL-60 细胞中增强 C1027 诱导的 DNA 阶梯形成和细胞毒性[3]。

[References]

[1]. ARCAMONE F, et, al. STRUCTURE AND SYNTHESIS OF DISTAMYCIN A. Nature. 1964 Sep 5;203:1064-5.

[2]. Hiraku Y, et, al. Distamycin A, a minor groove binder, changes enediyne-induced DNA cleavage sites and enhances apoptosis. Nucleic Acids Res Suppl. 2002;(2):95-6.

[3]. Majumder P, et, al. Effect of DNA groove binder distamycin A upon chromatin structure. PLoS One. 2011;6(10):e26486.

Chemical & Physical Properties

[ Density]:
1.45g/cm3

[ Molecular Formula ]:
C₂₂H₂₇N₉O₄

[ Molecular Weight ]:
481.50800

[ Exact Mass ]:
481.21900

[ PSA ]:
181.06000

[ LogP ]:
2.87670

[ Index of Refraction ]:
1.69

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WZ7108000

CAS REGISTRY NUMBER :: 636-47-5

LAST UPDATED :: 199612

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C22-H27-N9-O4

MOLECULAR WEIGHT :: 481.58

WISWESSER LINE NOTATION :: T5NJ A1 BVM2YZUM DMV- BT5NJ A1 DMV- BT5NJ A1 DMVH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 75 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - wild bird species

DOSE/DURATION :: 72 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: DNA damage

TEST SYSTEM :: Mammal - species unspecified Lymphocyte

DOSE/DURATION :: 500 umol/L

REFERENCE :: MLBRBU Molecular Biology Reports. (Dr. W. Junk Pub., POB 163, 3300 AD Dordrect, Netherlands) V.1- 1973- Volume(issue)/page/year: 2,135,1975

1H-Pyrrole-2-carboxamide,N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl]-4-[[[4-(formylamino)-1-methyl-1H-pyrrol-2-yl]carbonyl]amino]-1-methyl-

Names

Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds