Streptonigrin
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Hodoodo CAT#: H571001

CAS#: 3930-19-6 (R-isomer)

Description: Streptonigrin is an aminoquinone antitumor and antibacterial antibiotic produced by Streptomyces flocculus. Streptonigrin inhibits β-Catenin/Tcf signaling and shows cytotoxicity in β-catenin-activated cells. Streptonigrin induces delayed chromosomal instability involving interstitial telomeric sequences in Chinese hamster ovary cells. Note: Streptonigrin from natural resource is (-)-rotation, has CAS#3930-19-6 and is a R-isomer.


Chemical Structure

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Streptonigrin
CAS# 3930-19-6 (R-isomer)

Theoretical Analysis

Hodoodo Cat#: H571001
Name: Streptonigrin
CAS#: 3930-19-6 (R-isomer)
Chemical Formula: C25H22N4O8
Exact Mass: 506.14
Molecular Weight: 506.470
Elemental Analysis: C, 59.29; H, 4.38; N, 11.06; O, 25.27

Price and Availability

Size Price Availability Quantity
5mg USD 525
10mg USD 985
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Related CAS #: 1079893-79-0 (racemate)   3930-19-6 (R-isomer)   197730-37-3 (S-isomer)    

Synonym: Streptonigrin;; Valacidin; AO 50165L30; Bruneomycin; NSC 4538; NSC 56748; NSC 83950; Nigrin; Rufocromomycin; SN; STP; Streptonigran.

IUPAC/Chemical Name: 2-Pyridinecarboxylic acid, 5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-

InChi Key: PVYJZLYGTZKPJE-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,30H,26-27H2,1-4H3,(H,33,34)

SMILES Code: O=C(C1=NC(C2=NC3=C(C(C(OC)=C(N)C3=O)=O)C=C2)=C(N)C(C4=CC=C(OC)C(OC)=C4O)=C1C)O

Appearance: Dark-red to deep dark-red solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 506.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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6: Wang X, Kong D, Huang T, Deng Z, Lin S. StnK2 catalysing a Pictet-Spengler reaction involved in the biosynthesis of the antitumor reagent streptonigrin. Org Biomol Chem. 2018 Dec 5;16(47):9124-9128. doi: 10.1039/c8ob02710b. PubMed PMID: 30483694.

7: Lee SH, Lee WK, Kim N, Kang JH, Kim KH, Kim SG, Lee JS, Lee S, Lee J, Joo J, Kwon WS, Rha SY, Kim SY. Renal Cell Carcinoma Is Abrogated by p53 Stabilization through Transglutaminase 2 Inhibition. Cancers (Basel). 2018 Nov 19;10(11). pii: E455. doi: 10.3390/cancers10110455. PubMed PMID: 30463244; PubMed Central PMCID: PMC6267221.

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9: Doyle CR, Moon JY, Daily JP, Wang T, Pirofski LA. A Capsular Polysaccharide-Specific Antibody Alters Streptococcus pneumoniae Gene Expression during Nasopharyngeal Colonization of Mice. Infect Immun. 2018 Jun 21;86(7). pii: e00300-18. doi: 10.1128/IAI.00300-18. Print 2018 Jul. PubMed PMID: 29735523; PubMed Central PMCID: PMC6013671.

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16: Wizeman JW, Mohan R. Expression of peptidylarginine deiminase 4 in an alkali injury model of retinal gliosis. Biochem Biophys Res Commun. 2017 May 20;487(1):134-139. doi: 10.1016/j.bbrc.2017.04.031. Epub 2017 Apr 8. PubMed PMID: 28400047; PubMed Central PMCID: PMC5489915.

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18: Qian T, Wo J, Zhang Y, Song Q, Feng G, Luo R, Lin S, Wu G, Chen HF. Crystal Structure of StnA for the Biosynthesis of Antitumor Drug Streptonigrin Reveals a Unique Substrate Binding Mode. Sci Rep. 2017 Jan 11;7:40254. doi: 10.1038/srep40254. PubMed PMID: 28074848; PubMed Central PMCID: PMC5225493.

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