Quinocarcin
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Hodoodo CAT#: H581279

CAS#: 84573-33-1

Description: Quinocarcin are from Streptomyces melanovinaceus nov.sp. (-)-Quinocarcin are potent antitumor antibiotics that plays a key role in the construction of tetracyclic THIQ-pyrrolidine core scaffold.

Chemical Structure

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Quinocarcin
CAS# 84573-33-1
Instruction

Theoretical Analysis

Hodoodo Cat#: H581279
Name: Quinocarcin
CAS#: 84573-33-1
Chemical Formula: C18H22N2O4
Exact Mass: 330.16
Molecular Weight: 330.380
Elemental Analysis: C, 65.44; H, 6.71; N, 8.48; O, 19.37

Price and Availability

Size Price Availability Quantity
5mg USD 6200 2 weeks
15mg USD 17000 2 weeks
25mg USD 20500 2 weeks
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Synonym: Quinocarcin; Antibiotic DC 52; DC52; DC-52;

IUPAC/Chemical Name: 3,6-Imino-1H-2-oxa-11c-azanaphth(1,2,3-cd)azulene-5-carboxylic acid, 2a,3,4,5,6,6a,7,11b-octahydro-11-methoxy-12-methyl-, (2a-alpha,3-alpha,5-alpha,6-alpha,6a-alpha,11b-alpha)-, (-)-

InChi Key: VOUMVHRRAVBACH-MQZHMRIFSA-N

InChi Code: InChI=1S/C18H22N2O4/c1-19-12-7-10(18(21)22)16(19)11-6-9-4-3-5-14(23-2)15(9)13-8-24-17(12)20(11)13/h3-5,10-13,16-17H,6-8H2,1-2H3,(H,21,22)/t10-,11+,12+,13+,16-,17-/m0/s1

SMILES Code: O=C([C@@H]1[C@@]2([H])[C@](CC3=C4C(OC)=CC=C3)([H])N5[C@]4([H])CO[C@@]5([H])[C@@](N2C)([H])C1)O

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: To be determined

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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 330.38 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: Tang GL, Tang MC, Song LQ, Zhang Y. Biosynthesis of Tetrahydroisoquinoline Antibiotics. Curr Top Med Chem. 2016;16(15):1717-26. Review. PubMed PMID: 26456466.

2: Hiratsuka T, Koketsu K, Minami A, Kaneko S, Yamazaki C, Watanabe K, Oguri H, Oikawa H. Core assembly mechanism of quinocarcin/SF-1739: bimodular complex nonribosomal peptide synthetases for sequential mannich-type reactions. Chem Biol. 2013 Dec 19;20(12):1523-35. doi: 10.1016/j.chembiol.2013.10.011. Epub 2013 Nov 21. PubMed PMID: 24269153.

3: Chiba H, Sakai Y, Ohara A, Oishi S, Fujii N, Ohno H. Convergent synthesis of (-)-quinocarcin based on the combination of Sonogashira coupling and gold(I)-catalyzed 6-endo-dig hydroamination. Chemistry. 2013 Jul 1;19(27):8875-83. doi: 10.1002/chem.201300687. Epub 2013 May 16. PubMed PMID: 23681666.

4: Chiba H, Oishi S, Fujii N, Ohno H. Total synthesis of (-)-quinocarcin by gold(I)-catalyzed regioselective hydroamination. Angew Chem Int Ed Engl. 2012 Sep 3;51(36):9169-72. doi: 10.1002/anie.201205106. Epub 2012 Aug 13. PubMed PMID: 22890756.

5: Peng C, Pu JY, Song LQ, Jian XH, Tang MC, Tang GL. Hijacking a hydroxyethyl unit from a central metabolic ketose into a nonribosomal peptide assembly line. Proc Natl Acad Sci U S A. 2012 May 29;109(22):8540-5. doi: 10.1073/pnas.1204232109. Epub 2012 May 14. PubMed PMID: 22586110; PubMed Central PMCID: PMC3365175.

6: Huck L, González JF, de la Cuesta E, Menéndez JC, Avendaño C. 1,3-dipolar cycloadditions from tricyclic hemiaminals. Synthesis of the quinocarcin core through catalyst-free generation of azomethine ylides. Org Biomol Chem. 2011 Sep 21;9(18):6271-7. doi: 10.1039/c1ob05181d. Epub 2011 Jul 19. PubMed PMID: 21773620.

7: Kahsai AW, Zhu S, Fenteany G. G protein-coupled receptor kinase 2 activates radixin, regulating membrane protrusion and motility in epithelial cells. Biochim Biophys Acta. 2010 Feb;1803(2):300-10. doi: 10.1016/j.bbamcr.2009.11.002. Epub 2009 Nov 11. PubMed PMID: 19913059; PubMed Central PMCID: PMC2838949.

8: Allan KM, Stoltz BM. A concise total synthesis of (-)-quinocarcin via aryne annulation. J Am Chem Soc. 2008 Dec 24;130(51):17270-1. doi: 10.1021/ja808112y. PubMed PMID: 19035638.

9: Kahsai AW, Cui J, Kaniskan HU, Garner PP, Fenteany G. Analogs of tetrahydroisoquinoline natural products that inhibit cell migration and target galectin-3 outside of its carbohydrate-binding site. J Biol Chem. 2008 Sep 5;283(36):24534-45. doi: 10.1074/jbc.M800006200. Epub 2008 Jun 13. PubMed PMID: 18556657; PubMed Central PMCID: PMC2528994.

10: Wu YC, Liron M, Zhu J. Asymmetric total synthesis of (-)-quinocarcin. J Am Chem Soc. 2008 Jun 4;130(22):7148-52. doi: 10.1021/ja800662q. Epub 2008 May 3. PubMed PMID: 18454525.

11: Kahsai AW, Zhu S, Wardrop DJ, Lane WS, Fenteany G. Quinocarmycin analog DX-52-1 inhibits cell migration and targets radixin, disrupting interactions of radixin with actin and CD44. Chem Biol. 2006 Sep;13(9):973-83. PubMed PMID: 16984887.

12: Kwon S, Myers AG. Synthesis of (-)-quinocarcin by directed condensation of alpha-amino aldehydes. J Am Chem Soc. 2005 Dec 7;127(48):16796-7. PubMed PMID: 16316220.

13: Brown LM, Cowen RL, Debray C, Eustace A, Erler JT, Sheppard FC, Parker CA, Stratford IJ, Williams KJ. Reversing hypoxic cell chemoresistance in vitro using genetic and small molecule approaches targeting hypoxia inducible factor-1. Mol Pharmacol. 2006 Feb;69(2):411-8. Epub 2005 Oct 27. PubMed PMID: 16254058.

14: Herberich B, Scott JD, Williams RM. Synthesis of a netropsin conjugate of a water-soluble epi-quinocarcin analogue: the importance of stereochemistry at nitrogen. Bioorg Med Chem. 2000 Mar;8(3):523-32. PubMed PMID: 10732968.

15: Yamaguchi K, Fuse E, Takashima M, Yasuzawa T, Kuwabara T, Kobayashi S. Development of a sensitive liquid chromatography-electrospray ionization tandem mass spectrometry method for the measurement of 7-cyanoquinocarcinol in human plasma. J Chromatogr B Biomed Sci Appl. 1998 Aug 25;713(2):447-51. PubMed PMID: 9746263.

16: Flanagan ME, Rollins SB, Williams RM. Netropsin and spermine conjugates of a water-soluble quinocarcin analog: analysis of sequence-specific DNA interactions. Chem Biol. 1995 Mar;2(3):147-56. PubMed PMID: 9383416.

17: Plowman J, Dykes DJ, Narayanan VL, Abbott BJ, Saito H, Hirata T, Grever MR. Efficacy of the quinocarmycins KW2152 and DX-52-1 against human melanoma lines growing in culture kand in mice. Cancer Res. 1995 Feb 15;55(4):862-7. PubMed PMID: 7850800.

18: Williams RM, Flanagan ME, Tippie TN. O2-dependent cleavage of DNA by tetrazomine. Biochemistry. 1994 Apr 5;33(13):4086-92. PubMed PMID: 8142411.

19: Saito H, Hirata T, Kasai M, Fujimoto K, Ashizawa T, Morimoto M, Sato A. Synthesis and biological evaluation of quinocarcin derivatives: thioalkyl-substituted quinones and hydroquinones. J Med Chem. 1991 Jul;34(7):1959-66. PubMed PMID: 2066968.

20: Saito H, Sato A, Ashizawa T, Morimoto M, Hirata T. Synthesis of quinone derivatives of quinocarcin. Chem Pharm Bull (Tokyo). 1990 Dec;38(12):3202-10. PubMed PMID: 2092928.