Collismycin

• CAS: 158792-24-6
• Catalog Number: ACM158792246
• Category: Main Products
• Molecular Weight: 275.30
• Molecular Formula: C₁₃H₁₃N₃O₂S
• Synonyms: COLLISMYCIN A
• IUPAC Name: (2E)-4-methoxy-3-methylsulfanyl-2-(nitrosomethylidene)-6-pyridin-2-yl-1H-pyridine
• Canonical SMILES: COC1=C(C(=CN=O)NC(=C1)C2=CC=CC=N2)SC
• InChI Key: FXPSZLHFJDHOMI-DHZHZOJOSA-N
• Boiling Point: 381.2ºC at 760 mmHg
• Flash Point: 184.3ºC
• Density: 1.27 g/cm³
• Appearance: White to off white solid
• Exact Mass: 275.07300

Case Study

Synthesis of Potential Neuroprotective Derivatives of Collismycin A by Mutagenesis

Sialer, Carlos, et al. Bioorganic & medicinal chemistry letters, 2013, 23(20), 5707-5709.

Collismycin A is a natural product from the 2,2'-bipyridyl family, classified as a hybrid polyketide-nonribosomal peptide. Researchers inactivated a gene encoding a lysine 2-aminotransferase in the Streptomyces sp. CS40, the producer of collismycin A, through gene replacement. The resulting mutant could not synthesize collismycin A but regained this ability when picolinic acid (PA) was added to the culture medium.
By introducing various PA analogs to cultures of the mutant, which was blocked early in the PA biosynthesis pathway for collismycin A, two new derivatives, collismycin M4 and collismycin M6, were produced, both exhibiting neuroprotective properties. One derivative demonstrated greater activity than both the parent collismycin A and the positive control lipoic acid. These findings suggest that these compounds could serve as lead molecules for further development of potential neuroprotective agents.

Proteomic Evidence for Collismycin A as an Iron Chelator

Kawatani, Makoto, et al. Scientific reports, 2016, 6(1), 38385.

Collismycin A (CMA) is a microbial product with antiproliferative activity against cancer cells. To investigate its mechanism of action, this work reports the identification of molecular targets of CMA by ChemProteoBase, a proteome-based approach for drug target identification.
Proposed action mechanism of CMA
Collismycin A (CMA) is closely associated with the iron chelator di-2-pyridylketone 4,4-dimethyl-3-thiosemicarbazone. CMA can bind to both Fe(II) and Fe(III) ions, forming a 2:1 chelator-iron complex featuring a redox-inactive center. The cell growth inhibition caused by CMA was entirely reversed by the presence of Fe(II) and Fe(III) ions, but not by other metal ions like Zn(II) or Cu(II). Proteomic and transcriptomic analyses indicated that CMA influences the glycolytic pathway through the accumulation of HIF-1α. These findings imply that CMA functions as a specific iron chelator, resulting in the suppression of cancer cell proliferation.

Custom Q&A

What is the molecular formula of Collismycin?

The molecular formula of Collismycin is C13H13N3O2S.

What are the synonyms of Collismycin?

The synonyms of Collismycin are Collismycin B and (NZ)-N-[(4-methoxy-3-methylsulfanyl-6-pyridin-2-ylpyridin-2-yl)methylidene]hydroxylamine.

What is the molecular weight of Collismycin?

The molecular weight of Collismycin is 275.33 g/mol.

When was Collismycin created and modified?

Collismycin was created on January 15, 2019, and last modified on October 21, 2023.

What is the structure of Collismycin?

The structure of Collismycin can be viewed at the following link: https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?cid=135474257&t=l

What is the IUPAC name of Collismycin?

The IUPAC name of Collismycin is (NZ)-N-[(4-methoxy-3-methylsulfanyl-6-pyridin-2-ylpyridin-2-yl)methylidene]hydroxylamine.

What is the InChI of Collismycin?

The InChI of Collismycin is InChI=1S/C13H13N3O2S/c1-18-12-7-10(9-5-3-4-6-14-9)16-11(8-15-17)13(12)19-2/h3-8,17H,1-2H3/b15-8-.

What is the InChIKey of Collismycin?

The InChIKey of Collismycin is NQGMIPUYCWIEAW-NVNXTCNLSA-N.

What is the Canonical SMILES of Collismycin?

The Canonical SMILES of Collismycin is COC1=CC(=NC(=C1SC)C=NO)C2=CC=CC=N2.

What is the CAS number of Collismycin?

The CAS number of Collismycin is 158792-25-7.