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Streptonigrin

Product Name
Streptonigrin
CAS No.
3930-19-6
Chemical Name
Streptonigrin
Synonyms
NIGRIN;5278r.p.;nsc45383;NSC 83950;NSC 56748;valacidin;phaeomycin;BRUNEOMYCIN;AO 50165L302;streptonigran
CBNumber
CB1333569
Molecular Formula
C25H22N4O8
Formula Weight
506.46
MOL File
3930-19-6.mol
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Streptonigrin Property

Melting point:
301-303℃
Boiling point:
595.12°C (rough estimate)
Density 
1.4130 (rough estimate)
refractive index 
1.6000 (estimate)
storage temp. 
2-8°C
solubility 
Chloroform:Methanol (1:1): 2 mg/ml
form 
A solid
pka
6.2-6.4 (1:1 aq dioxane)
Merck 
13,8907
BRN 
599390
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Safety

Hazard Codes 
T+
Risk Statements 
28
Safety Statements 
53-28-36/37/39-45
RIDADR 
UN 3462 6.1/PG 1
WGK Germany 
3
RTECS 
TJ7350000
10-18
HazardClass 
6.1(a)
PackingGroup 
II
Toxicity
LD50 oral in mouse: 2330ug/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H300Fatal if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
S1014
Product name
Streptonigrin from Streptomyces flocculus
Purity
≥98%
Packaging
1mg
Price
$119
Updated
2024/03/01
Sigma-Aldrich
Product number
S1014
Product name
Streptonigrin from Streptomyces flocculus
Purity
≥98%
Packaging
5mg
Price
$432
Updated
2024/03/01
Cayman Chemical
Product number
27952
Product name
Streptonigrin
Packaging
1mg
Price
$118
Updated
2024/03/01
Cayman Chemical
Product number
27952
Product name
Streptonigrin
Packaging
5mg
Price
$529
Updated
2024/03/01
Usbiological
Product number
S7975-09
Product name
Streptonigrin
Packaging
1mg
Price
$490
Updated
2021/12/16
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Streptonigrin Chemical Properties,Usage,Production

Description

Streptonigrin is a phenylpyridylquinoline originally isolated from S. flocculus with diverse biological activities. Streptonigrin (2.5-12.5 μM) induces DNA cleavage by calf thymus topoisomerase II in a concentration-dependent manner. It induces phage production in S. typhimurium when used at concentrations ranging from 1 to 10 μg/ml. Streptonigrin (10 μg/ml) inhibits DNA synthesis in and reduces survival of S. typhimurium bacteria. Streptonigrin is bactericidal against E. coli in an iron-dependent manner, an effect that is blocked by the iron chelators deferoxamine and orthophenanthroline. Streptonigrin (40 nM) is cytotoxic to human HT-29 colon carcinoma cells but not to BE colon carcinoma cells in which NAD(P)H:quinone oxidoreductase is not expressed. Streptonigrin (0.001-0.1 μg/ml) inhibits mitosis and induces chromatin breaks in human leukocytes in a concentration-dependent manner. In vivo, streptonigrin (0.05 mg/kg, i.p.) increases the mean survival time in rats infected with Rauscher virus.

Chemical Properties

Brown to red solid. Soluble in polar solvents and alkaline solutions; insoluble in most nonpolar solvents and acid solutions.

Uses

Streptonigrin is an aminoquinone antitumour antibiotic. Its antineoplastic activity requires reductive activation by Xanthine-converting enzymes. It induces apoptosis by a mechanism involving NF-κB. DNA cleavage reaction and chromosome damage by Streptonigrin are influenced by the nature of the metal ion present and dependent on the production of free radicals. Its antibiotic activity is iron-activated. Streptonigrin from Streptomyces flocculus

Uses

Streptonigrin is an unusual aminoquinone with broad biological activity against bacteria, fungi, nematodes, viruses and tumour cells. Streptonigrin acts as a bioreductive agent, highly dependent on interactions with metal ions, notably iron, and plays an important role in free radical production through redox cycling of NAD(P)H:quinone oxidoreductase (NQO1).

Definition

ChEBI: Complex cytotoxic antibiotic obtained from Streptomyces flocculus or S. rufochronmogenus. It is used in advanced carcinoma and causes leukopenia.

brand name

Nigrin (Pfizer).

Biochem/physiol Actions

Streptonigrin (SN) is an aminoquinone antitumour antibiotic. Its antineoplastic activity requires reductive activation by Xanthine-converting enzymes. It induces apoptosis by a mechanism involving NF-κB. DNA cleavage reaction and chromosome damage by SN are influenced by the nature of the metal ion present and dependent on the production of free radicals. Its antibiotic activity is iron-activated.

Purification Methods

Streptonigrin is purified by TLC on pH 7-buffered silica gel plates (made from a slurry of Silica Gel 60 and 400mL of 0.05M phosphate buffer pH 7.0) and eluted with 5% MeOH/CHCl3. Material from the extracted band recrystallises from Me2CO or dioxane as almost black plates or needles. It is soluble in pyridine, Me2NCHO, aqueous NaHCO3 (some dec), and slightly soluble in MeOH, EtOH, EtOAc and H2O. It has UV max 248, 375-380nm ( 38,400 and 17,400). [Weinreb et al. J Am Chem Soc 104 536 1982, Rao et al. J Am Chem Soc 85 2532 1963.] Itis antineoplastic and causes severe bone marrow depression [Wilson et al. Antibiot Chemother 11 147 1961].

Streptonigrin Preparation Products And Raw materials

Raw materials

Preparation Products

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Streptonigrin Suppliers

9ding chemical ( Shanghai) Limited
Tel
4009209199
Fax
86-021-52271987
Email
sales@9dingchem.com
Country
China
ProdList
22519
Advantage
55
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-6206333 18521732826;
Fax
021-50323701
Email
market@aladdin-e.com
Country
China
ProdList
24835
Advantage
65
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399 18927568969
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4428
Advantage
55
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51471
Advantage
80
Shandong Xiya Chemical Co., Ltd.
Tel
4009903999 13395398332
Fax
0539-6365991
Email
sales@xiyashiji.com
Country
China
ProdList
20811
Advantage
60
Chengdu Dianchun Technology Co., Ltd
Tel
400-1166-196 18502815961
Fax
QQ:800101999
Email
cdhxsj@163.com
Country
China
ProdList
14623
Advantage
60
Anhui kuer Bioengineering Co., Ltd
Tel
0551-65171243 13810511747
Email
kuer@kuerhuaxue.com
Country
China
ProdList
2996
Advantage
55
Lynnchem
Tel
86-(0)29-85992781 17792393971
Email
info@lynnchem.com
Country
China
ProdList
4587
Advantage
58
Novachemistry
Tel
44-20819178-90 02081917890
Fax
(0)2080432064
Email
info@novachemistry.com
Country
United Kingdom
ProdList
4381
Advantage
58
Rhawn Reagent
Tel
400-400-1332688 18019345275
Fax
400-133-2688
Email
amy@rhawn.cn
Country
China
ProdList
15503
Advantage
58
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View Lastest Price from Streptonigrin manufacturers

Dideu Industries Group Limited
Product
Streptonigrin 3930-19-6
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-07-01
Shaanxi Dideu Medichem Co. Ltd
Product
Streptonigrin 3930-19-6
Price
US $0.00-0.00/Kg
Min. Order
1KG
Purity
99.0%
Supply Ability
800 ton
Release date
2020-04-30
Career Henan Chemical Co
Product
BRUNEOMYCIN 3930-19-6
Price
US $1.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100KG
Release date
2018-12-17

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