Quinomycin C

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 462814

CAS#: 11001-74-4

Description: Quinomycin C is an antitumor antibiotic. It removes and reverses the supercoiling of closed circular duplex DNA from bacteriophage PM2 in the fashion characteristic of intercalating drugs.

Chemical Structure

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Quinomycin C
CAS# 11001-74-4
Instruction

Theoretical Analysis

MedKoo Cat#: 462814
Name: Quinomycin C
CAS#: 11001-74-4
Chemical Formula: C55H72N12O12S2
Exact Mass: 1,156.48
Molecular Weight: 1,157.373
Elemental Analysis: C, 57.08; H, 6.27; N, 14.52; O, 16.59; S, 5.54

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Antibiotic U 48160; U48160; U 48160; U-48160;

IUPAC/Chemical Name: N,N'-(2,4,12,15,17,25-hexamethyl-11,24-bis(3-methylbutan-2-yl)-27-(methylthio)-3,6,10,13,16,19,23,26-octaoxo-9,22-dioxa-28-thia-2,5,12,15,18,25-hexaazabicyclo[12.12.3]nonacosane-7,20-diyl)bis(quinoxaline-2-carboxamide)

InChi Key: WNYOPINACXXCOV-UHFFFAOYSA-N

InChi Code: InChI=1S/C55H72N12O12S2/c1-27(2)29(5)42-53(76)78-24-40(63-46(69)38-23-57-34-19-15-17-21-36(34)61-38)48(71)59-32(8)50(73)67(12)44-52(75)66(11)43(30(6)28(3)4)54(77)79-25-39(62-45(68)37-22-56-33-18-14-16-20-35(33)60-37)47(70)58-31(7)49(72)64(9)41(51(74)65(42)10)26-81-55(44)80-13/h14-23,27-32,39-44,55H,24-26H2,1-13H3,(H,58,70)(H,59,71)(H,62,68)(H,63,69)

SMILES Code: CSC1SCC2N(C(C(NC(C(NC(c(cn3)nc4c3cccc4)=O)COC(C(N(C(C1N(C(C(NC(C(NC(c(cn5)nc6c5cccc6)=O)COC(C(N(C2=O)C)C(C(C)C)C)=O)=O)C)=O)C)=O)C)C(C(C)C)C)=O)=O)C)=O)C

Appearance: 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: >3 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 1,157.37 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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1: 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. PMID: 25471083.

2: 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. PMID: 26673007; PMCID: PMC4823101.

3: Lee JS, Waring MJ. Bifunctional intercalation and sequence specificity in the binding of quinomycin and triostin antibiotics to deoxyribonucleic acid. Biochem J. 1978 Jul 1;173(1):115-28. doi: 10.1042/bj1730115. PMID: 687363; PMCID: PMC1185755.

4: Yoshida T, Katagiri K. Influence of isoleucine upon quinomycin biosynthesis by Streptomyces sp. 732. J Bacteriol. 1967 Apr;93(4):1327-31. doi: 10.1128/JB.93.4.1327-1331.1967. PMID: 6032510; PMCID: PMC276604.

5: Lim CL, Nogawa T, Uramoto M, Okano A, Hongo Y, Nakamura T, Koshino H, Takahashi S, Ibrahim D, Osada H. RK-1355A and B, novel quinomycin derivatives isolated from a microbial metabolites fraction library based on NPPlot screening. J Antibiot (Tokyo). 2014 Apr;67(4):323-9. doi: 10.1038/ja.2013.144. Epub 2014 Feb 5. PMID: 24496142.

6: Shoji J, Konaka R, Kawano K, Higuchi N, Kyogoku Y. Presence of isomers in quinomycin E. J Antibiot (Tokyo). 1976 Nov;29(11):1246-8. doi: 10.7164/antibiotics.29.1246. PMID: 993112.

7: Hirose Y, Watanabe K, Minami A, Nakamura T, Oguri H, Oikawa H. Involvement of common intermediate 3-hydroxy-L-kynurenine in chromophore biosynthesis of quinomycin family antibiotics. J Antibiot (Tokyo). 2011 Jan;64(1):117-22. doi: 10.1038/ja.2010.142. Epub 2010 Nov 24. PMID: 21102595.

8: Watanabe K, Hotta K, Nakaya M, Praseuth AP, Wang CC, Inada D, Takahashi K, Fukushi E, Oguri H, Oikawa H. Escherichia coli allows efficient modular incorporation of newly isolated quinomycin biosynthetic enzyme into echinomycin biosynthetic pathway for rational design and synthesis of potent antibiotic unnatural natural product. J Am Chem Soc. 2009 Jul 8;131(26):9347-53. doi: 10.1021/ja902261a. PMID: 19514719; PMCID: PMC2757413.

9: Searle MS, Wickham G. Hoogsteen versus Watson-Crick A-T basepairing in DNA complexes of a new group of 'quinomycin-like' antibiotics. FEBS Lett. 1990 Oct 15;272(1-2):171-4. doi: 10.1016/0014-5793(90)80476-y. PMID: 2226828.

10: Fox KR. Footprinting studies of the interaction of quinomycin antibiotic UK63052 with DNA: comparison with echinomycin. J Antibiot (Tokyo). 1990 Oct;43(10):1307-15. doi: 10.7164/antibiotics.43.1307. PMID: 2175303.

11: Toda S, Sugawara K, Nishiyama Y, Ohbayashi M, Ohkusa N, Yamamoto H, Konishi M, Oki T. Quinaldopeptin, a novel antibiotic of the quinomycin family. J Antibiot (Tokyo). 1990 Jul;43(7):796-808. doi: 10.7164/antibiotics.43.796. PMID: 2387774.

12: Watanabe K, Hotta K, Praseuth AP, Searcey M, Wang CC, Oguri H, Oikawa H. Rationally engineered total biosynthesis of a synthetic analogue of a natural quinomycin depsipeptide in Escherichia coli. Chembiochem. 2009 Aug 17;10(12):1965-8. doi: 10.1002/cbic.200900260. PMID: 19588480; PMCID: PMC4556348.

13: Searle MS. Binding of quinomycin antibiotic UK-65,662 to DNA: 1H-n.m.r. studies of drug-induced changes in DNA conformation in complexes with d(ACGT)2 and d(GACGTC)2. Biochem J. 1994 Dec 15;304 ( Pt 3)(Pt 3):967-79. doi: 10.1042/bj3040967. PMID: 7818504; PMCID: PMC1137427.

14: Subramaniam D, Kaushik G, Dandawate P, Anant S. Targeting Cancer Stem Cells for Chemoprevention of Pancreatic Cancer. Curr Med Chem. 2018;25(22):2585-2594. doi: 10.2174/0929867324666170127095832. PMID: 28137215; PMCID: PMC5630517.

15: Steinerová N, Lipavská H, Stajner K, Cáslavská J, Blumauerová M, Cudlín J, Vanĕk Z. Production of quinomycin A in Streptomyces lasaliensis. Folia Microbiol (Praha). 1987;32(1):1-5. doi: 10.1007/BF02877251. PMID: 3817656.

16: Praseuth AP, Wang CC, Watanabe K, Hotta K, Oguri H, Oikawa H. Complete sequence of biosynthetic gene cluster responsible for producing triostin A and evaluation of quinomycin-type antibiotics from Streptomyces triostinicus. Biotechnol Prog. 2008 Nov-Dec;24(6):1226-31. doi: 10.1002/btpr.34. PMID: 19194935.

17: Yang Z, Shao L, Wang M, Rao M, Ge M, Xu Y. Two novel quinomycins discovered by UPLC-MS from Stretomyces sp. HCCB11876. J Antibiot (Tokyo). 2019 Mar;72(3):164-168. doi: 10.1038/s41429-018-0132-1. Epub 2018 Dec 18. PMID: 30560938.

18: 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. PMID: 4170544.

19: Rance MJ, Ruddock JC, Pacey MS, Cullen WP, Huang LH, Jefferson MT, Whipple EB, Maeda H, Tone J. UK-63,052 complex, new quinomycin antibiotics from Streptomyces braegensis subsp. japonicus; taxonomy, fermentation, isolation, characterisation and antimicrobial activity. J Antibiot (Tokyo). 1989 Feb;42(2):206-17. doi: 10.7164/antibiotics.42.206. PMID: 2925512.

20: Chen H, Patel DJ. Solution structure of a quinomycin bisintercalator-DNA complex. J Mol Biol. 1995 Feb 10;246(1):164-79. doi: 10.1006/jmbi.1994.0074. PMID: 7853395.