Quinomycin A

For research use only. Not for therapeutic Use.

  • CAT Number: M019914
  • CAS Number: 512-64-1
  • Molecular Formula: C51H64N12O12S2
  • Molecular Weight: 1101.30
  • Purity: ≥95%
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Quinomycin A(Cat No.:M019914)is a cyclic peptide antibiotic belonging to the quinoxaline family, known for its potent anti-tumor and antimicrobial activities. Derived from Streptomyces species, Quinomycin A intercalates with DNA, preventing DNA and RNA synthesis, which makes it effective in inhibiting the growth of cancer cells and various pathogens. Its selective cytotoxicity against certain tumor cells has drawn attention in cancer research, particularly in targeting resistant cancers. Due to its high bioactivity, Quinomycin A is extensively studied as a lead compound for developing novel anticancer and antibiotic therapies.


Catalog Number M019914
CAS Number 512-64-1
Synonyms

echinomycina;nsc526417;ECHINOMYCIN;QUINOMYCIN A;N-[(1R,4S,8R,11S,14R,17S,21R,24S)-3,11,13,16,24,26-hexamethyl-27-methylsulfanyl-2,5,9,12,15,18,22,25-octaoxo-4,17-di(propan-2-yl)-8-(quinoxaline-2-carbonylamino)-6,19-dioxa-28-thia-3,10,13,16,23,26-hexa

Molecular Formula C51H64N12O12S2
Purity ≥95%
Storage -20°C
IUPAC Name N-[2,4,12,15,17,25-hexamethyl-27-methylsulfanyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-20-(quinoxaline-2-carbonylamino)-9,22-dioxa-28-thia-2,5,12,15,18,25-hexazabicyclo[12.12.3]nonacosan-7-yl]quinoxaline-2-carboxamide
InChI InChI=1S/C51H64N12O12S2/c1-25(2)38-49(72)74-22-36(59-42(65)34-21-53-30-17-13-15-19-32(30)57-34)44(67)55-28(6)46(69)63(10)40-48(71)62(9)39(26(3)4)50(73)75-23-35(58-41(64)33-20-52-29-16-12-14-18-31(29)56-33)43(66)54-27(5)45(68)60(7)37(47(70)61(38)8)24-77-51(40)76-11/h12-21,25-28,35-40,51H,22-24H2,1-11H3,(H,54,66)(H,55,67)(H,58,64)(H,59,65)
InChIKey AUJXLBOHYWTPFV-UHFFFAOYSA-N
SMILES CC1C(=O)N(C2CSC(C(C(=O)N(C(C(=O)OCC(C(=O)N1)NC(=O)C3=NC4=CC=CC=C4N=C3)C(C)C)C)N(C(=O)C(NC(=O)C(COC(=O)C(N(C2=O)C)C(C)C)NC(=O)C5=NC6=CC=CC=C6N=C5)C)C)SC)C
Reference

1: Ponnurangam S, Dandawate PR, Dhar A, Tawfik OW, Parab RR, Mishra PD, Ranadive
P, Sharma R, Mahajan G, Umar S, Weir SJ, Sugumar A, Jensen RA, Padhye SB,
Balakrishnan A, Anant S, Subramaniam D. Quinomycin A targets Notch signaling
pathway in pancreatic cancer stem cells. Oncotarget. 2016 Jan 19;7(3):3217-32.
doi: 10.18632/oncotarget.6560. PubMed PMID: 26673007; PubMed Central PMCID:
PMC4823101.

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2: Hayase H, Watanabe N, Lim CL, Nogawa T, Komatsuya K, Kita K, Osada H.
Inhibition of malaria parasite growth by quinomycin A and its derivatives through
DNA-intercalating activity. Biosci Biotechnol Biochem. 2015;79(4):633-5. doi:
10.1080/09168451.2014.987205. Epub 2014 Dec 4. PubMed PMID: 25471083.
<br>

3: Steinerová N, Lipavská H, Stajner K, Cáslavská J, Blumauerová M, Cudlín J,
Van&#277;k Z. Production of quinomycin A in Streptomyces lasaliensis. Folia Microbiol
(Praha). 1987;32(1):1-5. PubMed PMID: 3817656.
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4: Sato K, Niinomi Y, Katagiri K, Matsukage A, Minagawa T. Prevention of phage
multiplication by quinomycin A. Biochim Biophys Acta. 1969 Jan 21;174(1):230-8.
PubMed PMID: 4885693.
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5: Sato K, Shiratori O, Katagiri K. The mode of action of quinoxaline
antibiotics. Interaction of quinomycin A with deoxyribonucleic acid. J Antibiot
(Tokyo). 1967 Sep;20(5):270-6. PubMed PMID: 4170544.
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6: KATAGIRI K, SHOJI J, YOSHISA T. Identity of levomycin and quinomycin A
(echimomycin). J Antibiot (Tokyo). 1962 Nov;15:273. PubMed PMID: 14042112.

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