Resistomycin | CAS# 20004-62-0 | Antibiotic

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

MedKoo CAT#: 571100

CAS#: 20004-62-0

Description: Resistomycin is an antibiotic from Streptomyces resistomycificus, also known as the trademark for kanamycin A sulfate. It is being assessed as an anticancer compound. It has also been tested for use as a therapeutic agent against tuberculosis.

Chemical Structure

Resistomycin

CAS# 20004-62-0

Instruction

Theoretical Analysis

MedKoo Cat#: 571100
Name: Resistomycin
CAS#: 20004-62-0
Chemical Formula: C22H16O6
Exact Mass: 376.09
Molecular Weight: 376.360
Elemental Analysis: C, 70.21; H, 4.29; O, 25.51

Price and Availability

Size	Price	Availability
1mg	USD 370	2 Weeks
5mg	USD 970	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Resistomycin; Croceomycin; Geliomycin; Itamycin; A 3733A; A-3733A; A3733A; Antibiotic 3733A

IUPAC/Chemical Name: 2H-Benzo(cd)pyrene-2,6(1H)-dione, 3,5,7,10-tetrahydroxy-1,1,9-trimethyl-

InChi Key: ABLACSIRCKEUOB-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H16O6/c1-7-4-9(23)15-18-13(7)10(24)5-8-14(18)19-16(20(15)27)11(25)6-12(26)17(19)21(28)22(8,2)3/h4-6,23-26H,1-3H3

SMILES Code: O=C(C1=C(O)C=C(O)C2=C1C3=C45)C(C)(C)C3=CC(O)=C5C(C)=CC(O)=C4C2=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: 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

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 376.36 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.

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: Carlson S, Tanouye U, Omarsdottir S, Murphy BT. Phylum-specific regulation of resistomycin production in a Streptomyces sp. via microbial coculture. J Nat Prod. 2015 Mar 27;78(3):381-7. doi: 10.1021/np500767u. Epub 2014 Dec 24. PubMed PMID: 25537064.

2: Vijayabharathi R, Sathyadevi P, Krishnamoorthy P, Senthilraja D, Brunthadevi P, Sathyabama S, Priyadarisini VB. Interaction studies of resistomycin from Streptomyces aurantiacus AAA5 with calf thymus DNA and bovine serum albumin. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Apr;89:294-300. doi: 10.1016/j.saa.2011.12.072. Epub 2011 Dec 31. PubMed PMID: 22285949.

3: Vijayabharathi R, Bruheim P, Andreassen T, Raja DS, Devi PB, Sathyabama S, Priyadarisini VB. Assessment of resistomycin, as an anticancer compound isolated and characterized from Streptomyces aurantiacus AAA5. J Microbiol. 2011 Dec;49(6):920-6. doi: 10.1007/s12275-011-1260-5. Epub 2011 Dec 28. PubMed PMID: 22203554.

4: Zhang YL, Li S, Jiang DH, Kong LC, Zhang PH, Xu JD. Antifungal activities of metabolites produced by a termite-associated Streptomyces canus BYB02. J Agric Food Chem. 2013 Feb 20;61(7):1521-4. doi: 10.1021/jf305210u. Epub 2013 Feb 8. PubMed PMID: 23360202.

5: Shiono Y, Shiono N, Seo S, Oka S, Yamazaki Y. Effects of polyphenolic anthrone derivatives, resistomycin and hypercin, on apoptosis in human megakaryoblastic leukemia CMK-7 cell line. Z Naturforsch C. 2002 Sep-Oct;57(9-10):923-9. PubMed PMID: 12440735.

6: Fritzsche K, Ishida K, Hertweck C. Orchestration of discoid polyketide cyclization in the resistomycin pathway. J Am Chem Soc. 2008 Jul 2;130(26):8307-16. doi: 10.1021/ja800251m. Epub 2008 Jun 6. PubMed PMID: 18533655.

7: Jakobi K, Hertweck C. A gene cluster encoding resistomycin biosynthesis in Streptomyces resistomycificus; exploring polyketide cyclization beyond linear and angucyclic patterns. J Am Chem Soc. 2004 Mar 3;126(8):2298-9. PubMed PMID: 14982421.

8: Ishida K, Fritzsche K, Hertweck C. Geminal tandem C-methylation in the discoid resistomycin pathway. J Am Chem Soc. 2007 Oct 24;129(42):12648-9. Epub 2007 Oct 3. PubMed PMID: 17914826.

9: Rosenbrook W Jr. The structure of resistomycin. J Org Chem. 1967 Sep;32(9):2924-5. PubMed PMID: 6073224.

10: Ishida K, Maksimenka K, Fritzsche K, Scherlach K, Bringmann G, Hertweck C. The boat-shaped polyketide resistoflavin results from re-facial central hydroxylation of the discoid metabolite resistomycin. J Am Chem Soc. 2006 Nov 15;128(45):14619-24. PubMed PMID: 17090047.

11: Roggo BE, Petersen F, Delmendo R, Jenny HB, Peter HH, Roesel J. 3-Alkanoyl-5-hydroxymethyl tetronic acid homologues and resistomycin: new inhibitors of HIV-1 protease. I. Fermentation, isolation and biological activity. J Antibiot (Tokyo). 1994 Feb;47(2):136-42. PubMed PMID: 8150707.

12: Haupt I, Wähnert U, Pitra C, Löber G, Luck G, Eckardt K. Effects of the antibiotic resistomycin on the synthesis of macromolecules. Z Allg Mikrobiol. 1975;15(6):411-21. PubMed PMID: 812270.

13: Brockmann H, Reschke T. [The composition of resistomycin]. Tetrahedron Lett. 1968 May;(27):3167-70. German. PubMed PMID: 5651014.

14: OSSWALD W. [Clinical trials on Resistomycin in the treatment of pulmonary tuberculosis]. Med Klin. 1961 Dec 8;56:2088-91. German. PubMed PMID: 14482564.

15: Lankapalli AR, Kannabiran K. Interaction of marine Streptomyces compounds with selected cancer drug target proteins by in silico molecular docking studies. Interdiscip Sci. 2013 Mar;5(1):37-44. doi: 10.1007/s12539-013-0146-0. Epub 2013 Apr 19. PubMed PMID: 23605638.

16: Haupt I, Eckardt K. [Effect of the antibiotics resistomycin and resistoflavin on growth, nucleic acid and protein synthesis in Bacillus subtilis]. Z Allg Mikrobiol. 1972;12(7):575-81. German. PubMed PMID: 4197364.

17: Brockmann H, Reschke T. [On the tautomerism of resistomycin]. Naturwissenschaften. 1968 Nov;55(11):544. German. PubMed PMID: 5727498.

18: Sajid I, Shaaban KA, Hasnain S. Antitumour compounds from a saline soil isolate, Streptomyces griseoincarnatus CTF15. Nat Prod Res. 2011 Mar;25(5):549-59. doi: 10.1080/14786419.2010.534993. PubMed PMID: 21391117.

19: Dobrev P, Slaveykova A, Lankova D. On the treatment of primary tuberculosis in tender age (0-5 years) with resistomycin, cycloserine, and ethionamid. Nauchni Tr Vissh Med Inst Sofiia. 1966;45(5):37-42. PubMed PMID: 4228990.

20: Silvennoinen L, Sandalova T, Schneider G. The polyketide cyclase RemF from Streptomyces resistomycificus contains an unusual octahedral zinc binding site. FEBS Lett. 2009 Sep 3;583(17):2917-21. doi: 10.1016/j.febslet.2009.07.061. Epub 2009 Aug 6. PubMed PMID: 19665022.

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