Kinamycin
{{Short description|Group of chemical compounds}}
Kinamycins are a group of bacterial polyketide secondary metabolites containing a diazo group. Kinamycins are known for their cytotoxicity and are considered of interest for potential use in anti-cancer therapies.{{Cite journal| doi = 10.1016/j.tetlet.2008.03.019| title = Kinamycin-mediated DNA cleavage under biomimetic conditions| year = 2008| last1 = Ballard | first1 = T. E.| last2 = Melander | first2 = C.| journal = Tetrahedron Letters| volume = 49| issue = 19| pages = 3157 }}{{Cite journal | doi = 10.1016/j.freeradbiomed.2007.07.005 | pmc = 2753228 | pmid = 17854709 | title = Mechanism of the cytotoxicity of the diazoparaquinone antitumor antibiotic kinamycin F | year = 2007 | last1 = O'Hara | first1 = K. A. | last2 = Wu | first10 = B. B. | first2 = X. | last3 = Patel | first3 = D. | last4 = Liang | first4 = H. | last10 = Hasinoff | last5 = Yalowich | first5 = J. C. | last6 = Chen | first6 = N. | last7 = Goodfellow | first7 = V. | last8 = Adedayo | first8 = O. | last9 = Dmitrienko | first9 = G. I. | journal = Free Radical Biology and Medicine | volume = 43 | issue = 8 | pages = 1132–1144 }}
Synthesis
In 2006 and 2007 the means to totally and enantioselectively synthesize kinamycins C, F, and J were discovered.{{Cite journal| last1 = Lei | first1 = X.| last2 = Porco Ja | first2 = J.| title = Total synthesis of the diazobenzofluorene antibiotic (-)-kinamycin C1| journal = Journal of the American Chemical Society| volume = 128| issue = 46| pages = 14790–14791| year = 2006| pmid = 17105273 | doi = 10.1021/ja066621v}}{{Cite journal | doi = 10.1021/ja074297d | title = Total Synthesis of Kinamycins C, F, and J | year = 2007 | last1 = Nicolaou | first1 = K. C. | last2 = Li | first2 = H. | last3 = Nold | first3 = A. L. | last4 = Pappo | first4 = D. | last5 = Lenzen | first5 = A. | journal = Journal of the American Chemical Society | volume = 129 | pages = 10356–7| pmid = 17676854 | issue = 34 }} In 2010 a method was found to allow easier synthesis of these compounds in fewer steps, making research into their properties more feasible.{{Cite journal | doi = 10.1021/ja910769j | title = Development of a Convergent Entry to the Diazofluorene Antitumor Antibiotics: Enantioselective Synthesis of Kinamycin F | year = 2010 | last1 = Woo | first1 = C. M. | last2 = Lu | first2 = L. | last3 = Gholap | first3 = S. L. | last4 = Smith | first4 = D. R.| last5 = Herzon | first5 = S. B. | journal = Journal of the American Chemical Society | volume = 132 | pages = 2540–1| pmid = 20141138 | issue = 8 }}
References
External links
- EMBL-EBI listing—includes links to structural formula and other properties of group members [http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI%3A48207 kinamycin (CHEBI:48207)]
- [http://ccc.chem.pitt.edu/wipf/Current%20Literature/John_5.pdf Description of Porco(2006) and Nicolaou(2007) synthesis on University of Pittsburgh site]