Jadomycin B

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

MedKoo CAT#: 596096

CAS#: 149633-99-8

Description: A jadomycin is an angucyclic natural product produced by Streptomyces venezuelae ISP5230 (ATCC10712), the producing organism of the antibiotic chloramphenicol.


Chemical Structure

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Jadomycin B
CAS# 149633-99-8

Theoretical Analysis

MedKoo Cat#: 596096
Name: Jadomycin B
CAS#: 149633-99-8
Chemical Formula: C30H31NO9
Exact Mass: 549.1999
Molecular Weight: 549.57
Elemental Analysis: C, 65.57; H, 5.69; N, 2.55; O, 26.20

Size Price Shipping out time Quantity
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Pricing updated 2021-03-05. Prices are subject to change without notice.

Jadomycin B is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Synonym: Jadomycin B;

IUPAC/Chemical Name: 1-(sec-butyl)-12-((4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-7-hydroxy-5-methyl-8H-benzo[b]oxazolo[3,2-f]phenanthridine-2,8,13(1H,3aH)-trione

InChi Key: BSBSCJRAEMDCHC-UHFFFAOYSA-N

InChi Code: InChI=1S/C30H31NO9/c1-5-13(3)24-30(37)40-29-16-9-12(2)10-17(32)21(16)23-25(31(24)29)28(36)22-15(27(23)35)7-6-8-19(22)39-20-11-18(33)26(34)14(4)38-20/h6-10,13-14,18,20,24,26,29,32-34H,5,11H2,1-4H3

SMILES Code: O=C1C(C(C)CC)N2C3=C(C(C4=CC=CC(OC5CC(C(C(C)O5)O)O)=C4C3=O)=O)C6=C(C=C(C)C=C6O)C2O1

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:
>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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 549.57 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.

Select a batch to recalculate based on the batch molecular weight:
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

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1: Hall SR, Toulany J, Bennett LG, Martinez-Farina CF, Robertson AW, Jakeman DL, Goralski KB. Jadomycins Inhibit Type II Topoisomerases and Promote DNA Damage and Apoptosis in Multidrug-Resistant Triple-Negative Breast Cancer Cells. J Pharmacol Exp Ther. 2017 Nov;363(2):196-210. doi: 10.1124/jpet.117.241125. Epub 2017 Sep 13. PubMed PMID: 28904004.

2: Li L, Pan G, Zhu X, Fan K, Gao W, Ai G, Ren J, Shi M, Olano C, Salas JA, Yang K. Engineered jadomycin analogues with altered sugar moieties revealing JadS as a substrate flexible O-glycosyltransferase. Appl Microbiol Biotechnol. 2017 Jul;101(13):5291-5300. doi: 10.1007/s00253-017-8256-y. Epub 2017 Apr 20. PubMed PMID: 28429060.

3: Zhu J, Sun D, Liu W, Chen Z, Li J, Wen Y. AvaR2, a pseudo γ-butyrolactone receptor homologue from Streptomyces avermitilis, is a pleiotropic repressor of avermectin and avenolide biosynthesis and cell growth. Mol Microbiol. 2016 Nov;102(4):562-578. doi: 10.1111/mmi.13479. Epub 2016 Aug 25. PubMed PMID: 27502190.

4: Wang W, Yang T, Li Y, Li S, Yin S, Styles K, Corre C, Yang K. Development of a Synthetic Oxytetracycline-Inducible Expression System for Streptomycetes Using de Novo Characterized Genetic Parts. ACS Synth Biol. 2016 Jul 15;5(7):765-73. doi: 10.1021/acssynbio.6b00087. Epub 2016 May 6. PubMed PMID: 27100123.

5: Li S, Wang J, Li X, Yin S, Wang W, Yang K. Genome-wide identification and evaluation of constitutive promoters in streptomycetes. Microb Cell Fact. 2015 Oct 29;14:172. doi: 10.1186/s12934-015-0351-0. PubMed PMID: 26515616; PubMed Central PMCID: PMC4625935.

6: Martinez-Farina CF, Jakeman DL. Jadomycins, put a bigger ring in it: isolation of seven- to ten-membered ring analogues. Chem Commun (Camb). 2015 Oct 7;51(78):14617-9. doi: 10.1039/c5cc05571g. Erratum in: Chem Commun (Camb). 2018 Mar 26;:. PubMed PMID: 26288855.

7: Robertson AW, Martinez-Farina CF, Syvitski RT, Jakeman DL. Characterization of l-Digitoxosyl-phenanthroviridin from Streptomyces venezuelae ISP5230. J Nat Prod. 2015 Aug 28;78(8):1942-8. doi: 10.1021/acs.jnatprod.5b00277. Epub 2015 Jul 23. PubMed PMID: 26203536.

8: Wang W, Ji J, Li X, Wang J, Li S, Pan G, Fan K, Yang K. Angucyclines as signals modulate the behaviors of Streptomyces coelicolor. Proc Natl Acad Sci U S A. 2014 Apr 15;111(15):5688-93. doi: 10.1073/pnas.1324253111. Epub 2014 Mar 28. PubMed PMID: 24706927; PubMed Central PMCID: PMC3992645.

9: Zhang Y, Pan G, Zou Z, Fan K, Yang K, Tan H. JadR*-mediated feed-forward regulation of cofactor supply in jadomycin biosynthesis. Mol Microbiol. 2013 Nov;90(4):884-97. doi: 10.1111/mmi.12406. Epub 2013 Oct 17. PubMed PMID: 24112541.

10: Zhang Y, Zou Z, Niu G, Tan H. JadR and jadR2 act synergistically to repress jadomycin biosynthesis. Sci China Life Sci. 2013 Jul;56(7):584-90. doi: 10.1007/s11427-013-4508-y. Epub 2013 Jul 6. PubMed PMID: 23832247.

11: Yang X, Yu B. Total synthesis of jadomycins B, S, T, and ILEVS1080. Chemistry. 2013 Jun 24;19(26):8431-4. doi: 10.1002/chem.201301297. Epub 2013 May 13. PubMed PMID: 23670961.

12: Peng X, Ji J, Zhang X, Fan K, Jin L, Zhang Y, Yang K. [Identification of key residues in the catalytic center JadH involved in binding substrates or catalysis of jadomycin biosynthesis]. Sheng Wu Gong Cheng Xue Bao. 2012 Aug;28(8):950-8. Chinese. PubMed PMID: 23185895.

13: Fan K, Pan G, Peng X, Zheng J, Gao W, Wang J, Wang W, Li Y, Yang K. Identification of JadG as the B ring opening oxygenase catalyzing the oxidative C-C bond cleavage reaction in jadomycin biosynthesis. Chem Biol. 2012 Nov 21;19(11):1381-90. doi: 10.1016/j.chembiol.2012.09.009. PubMed PMID: 23177193.

14: Peng X, Ji J, Zhang Y, Yang K, Zhang H, Zhu H. [Progress in the understanding of the function of atypical response regulators: a review]. Sheng Wu Gong Cheng Xue Bao. 2012 May;28(5):531-9. Review. Chinese. PubMed PMID: 22916491.

15: Sun W, Peng C, Zhao Y, Li Z. Functional gene-guided discovery of type II polyketides from culturable actinomycetes associated with soft coral Scleronephthya sp. PLoS One. 2012;7(8):e42847. doi: 10.1371/journal.pone.0042847. Epub 2012 Aug 7. PubMed PMID: 22880121; PubMed Central PMCID: PMC3413676.

16: Fan K, Zhang X, Liu H, Han H, Luo Y, Wang Q, Geng M, Yang K. Evaluation of the cytotoxic activity of new jadomycin derivatives reveals the potential to improve its selectivity against tumor cells. J Antibiot (Tokyo). 2012 Sep;65(9):449-52. doi: 10.1038/ja.2012.48. Epub 2012 Jun 20. PubMed PMID: 22714025.

17: Kharel MK, Pahari P, Shepherd MD, Tibrewal N, Nybo SE, Shaaban KA, Rohr J. Angucyclines: Biosynthesis, mode-of-action, new natural products, and synthesis. Nat Prod Rep. 2012 Feb;29(2):264-325. doi: 10.1039/c1np00068c. Epub 2011 Dec 21. Review. PubMed PMID: 22186970.

18: Dupuis SN, Veinot T, Monro SM, Douglas SE, Syvitski RT, Goralski KB, McFarland SA, Jakeman DL. Jadomycins derived from the assimilation and incorporation of norvaline and norleucine. J Nat Prod. 2011 Nov 28;74(11):2420-4. doi: 10.1021/np200689w. Epub 2011 Nov 3. PubMed PMID: 22050382.

19: Kubiak RL, Holden HM. Combined structural and functional investigation of a C-3''-ketoreductase involved in the biosynthesis of dTDP-L-digitoxose. Biochemistry. 2011 Jul 5;50(26):5905-17. doi: 10.1021/bi200514b. Epub 2011 Jun 8. PubMed PMID: 21598943.

20: Monro SM, Cottreau KM, Spencer C, Wentzell JR, Graham CL, Borissow CN, Jakeman DL, McFarland SA. Copper-mediated nuclease activity of jadomycin B. Bioorg Med Chem. 2011 Jun 1;19(11):3357-60. doi: 10.1016/j.bmc.2011.04.043. Epub 2011 Apr 29. PubMed PMID: 21565515.