2012
DOI: 10.1021/np200861n
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Symplocin A, a Linear Peptide from the Bahamian Cyanobacterium Symploca sp. Configurational Analysis of N,N-Dimethylamino Acids by Chiral-Phase HPLC of Naphthacyl Esters

Abstract: The absolute stereostructures of the components of symplocin A (3), a new N,N-dimethyl-terminated peptide from the Bahamian cyanobacterium, Symploca sp., were assigned from spectroscopic analysis, including MS and 2D NMR and Marfey’s analysis. The complete absolute configuration of symplocin A, including the unexpected D-configurations of the terminal N,N-dimethylisoleucine and valic acid residues, were assigned by chiral-phase HPLC of the corresponding 2-naphthacyl esters, a highly sensitive, complementary st… Show more

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Cited by 37 publications
(36 citation statements)
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“…28 An analog of dolastatin 10, TZT-1027 (auristatin PE or soblidotin), which differs from dolastatin 10 only in the absence of the thiazoline ring from the dolaphenine residue, was found to be effective in two human xenograft models, MX-1 breast carcinoma and LX-1 lung carcinoma in mice. 29 It showed equivalent efficacy against both p53 normal and mutant cell lines, 30,31 demonstrating that a conjugate of auristatin with a monoclonal antibody directed to the adhesion molecule E-selectin can inhibit the growth of prostate cancer cells.…”
Section: Dolastatin 10mentioning
confidence: 99%
“…28 An analog of dolastatin 10, TZT-1027 (auristatin PE or soblidotin), which differs from dolastatin 10 only in the absence of the thiazoline ring from the dolaphenine residue, was found to be effective in two human xenograft models, MX-1 breast carcinoma and LX-1 lung carcinoma in mice. 29 It showed equivalent efficacy against both p53 normal and mutant cell lines, 30,31 demonstrating that a conjugate of auristatin with a monoclonal antibody directed to the adhesion molecule E-selectin can inhibit the growth of prostate cancer cells.…”
Section: Dolastatin 10mentioning
confidence: 99%
“…Albeit an IC 50 for enzyme or receptor inhibition is provided, no mechanism of action studies were reported at the time of publication: alotaketal C ( 224 ) [215]; aspergentisyl A ( 225 ) [216]; A. terreus butyrolactone ( 226 ) [217]; caulerpine ( 227 ) [218]; conicasterol F ( 228 ) [219]; D. avara sesquiterpene ( 229 ) [220]; D. gigantea sterols ( 230 , 231 ) [221]; dysidavarone A ( 232 ) [222]; galvaquinone B ( 233 ) [223]; halicloic acids A and B ( 234 , 235 ) [224]; isochromophilone XI ( 236 ) [225]; leucettamols A and B ( 237 , 238 ) [226]; manadosterol A ( 239 ) [227]; marilines A1 and A2 ( 240 , 241 ) [228]; methyl sarcotroate B ( 242 ) [229]; P. citrinum sorbicillinoid ( 243 ) [230]; phosphoiodyn A ( 244 ) [231]; purpuroines A and D ( 245 , 246 ) [232]; santacruzamate A ( 247 ) [233]; sarcophytonolide N ( 248 ) [234]; sargassumol ( 249 ) [235]; sesquibastadin 1 ( 250 ) [236]; S. glaucum cembranoids ( 251 – 253 ) [237]; symplocin A ( 254 ) [238]; tsitsikammamine A derivative ( 255 ) [239]; V. lanosa bromophenol ( 256 ) [240] ; and X. testudinaria fatty acid ( 257 ) [241]. …”
Section: Marine Compounds With Miscellaneous Mechanisms Of Actionmentioning
confidence: 99%
“…10A), from a Symploca sp. collection also demonstrated selective and potent inhibitory activity against cathepsin E. 157 …”
Section: Mechanisms Of Action and Direct Cellular Targets Of Biologmentioning
confidence: 97%