Sun, D., Park, H., & Hurley, L. H. (1993). Alkylation of guanine and cytosine in DNA by bizelesin. Evidence for a covalent immobilization leading to a proximity-driven alkylation of normally unreactive bases by a (+)-CC-1065 cross-linking compound. Chemical Research in Toxicology, 6(6), 889-894.
PMID: 8117929;Abstract:
Bizelesin, an intrahelical DNA-DNA interstrand cross-linker related to (+)-CC-1065, has been shown to alkylate DNA through guanine in restriction enzyme sequences in which there is a suitably positioned adenine contained in a highly reactive monoalkylation sequence on the opposite strand. Oligomers containing the sequence 5′-TTTTTN*, in which "N" was either G, C, or T, were synthesized to evaluate the cross-linking potential of bizelesin at nonadenine bases. Kinetic analysis of monoalkylation and cross-linking events demonstrates that it is the reaction at "N" (guanine or cytosine) that results in the cross-link which is the slow step. On the basis of this analysis and the normal unreactivity of guanine and cytosine to alkylation by the cyclopropapyrroloindole alkylating moiety of (+)-CC-1065, we propose that the molecular mechanism for this type of cross-linking reaction most likely involves a covalent immobilization of the second alkylating arm, resulting in a "proximity-driven" reaction. © 1993 American Chemical Society.
Grand, C. L., Powell, T. J., Nagle, R. B., Bearss, D. J., Tye, D., Gleason-Guzman, M., & Hurley, L. H. (2005). Mutations in the G-quadruplex silencer element and their relationship to c-MYC overexpression, NM23 repression, and therapeutic rescue.. Proceedings of the National Academy of Sciences of the United States of America, 102(2), 516-.
PMID: 15696627;PMCID: PMC544325;
Kshirsagar, T. A., & Hurley, L. H. (1998). Erratum: A facile synthesis of 5-mesyl-3-benzylbenze[e]indole: Implications for the involvement of a p-quinone methide intermediate (Journal of Organic Chemistry (1998) 63 (5724)). Journal of Organic Chemistry, 63(25), 9604-.
Tao, L. u., & Hurley, L. H. (2004). Synthesis of 5,10,15,20-tetra(N-methyl-6-quinolyl)-21,23-dithiaporphyrin chloride as cationic core-modified porphyrin. Chinese Chemical Letters, 15(11), 1261-1264.
Abstract:
First cationic 6-quinolyl substituted dithiaporphyrin was synthesized using Skraup quinoline methodology from thiaporphyrin bearing 4-acetamidophenyl prepared by condensation reaction of aromatic aldehyde with pyrrole.
Brahme, N. M., Gonzalez, J. E., Mizsak, S., Rolls, J. R., Hessler, E. J., & Hurley, L. H. (1984). Biosynthesis of the lincomycins. 2. Studies using stable isotopes on the biosynthesis of methylthiolincosaminide moiety of lincomycin A. Journal of the American Chemical Society, 106(25), 7878-7883.
Abstract:
Lincomycin is an antibiotic produced by Streptomyces lincolnensis and consists of a unique aminooctose moiety, α-methylthiolincosaminide (MTL), attached via an amide linkage to a propylhygric acid unit. The biosynthesis of the MTL moiety of lincomycin has been investigated by using both specifically carbon-13 labeled substrates and uniformly carbon-13 labeled D-glucose. In the latter case 13C-13C spin coupling patterns in lincomycin and MTL were used to determine those carbon atoms from glucose that remained intact during their conversion to the antibiotic. By combination of the biosynthetic information obtained from the 13C-13C spin coupling patterns with that from those carbon atoms in MTL which were enriched from carbon-13 specifically labeled molecules, conclusions can be drawn about likely pathways and intermediates between glucose and MTL. The C8-carbon skeleton of MTL is assembled through condensation of a pentose unit (C5) and a C3 unit. The C5 unit can be assembled in two ways. Either it is derived from glucose via the hexose monophosphate shunt (HMPS) as an intact unit or it is assembled from condensation of a C3 unit (glyceraldehyde 3-phosphate) with a C2-unit donor such as sedoheptulose 7-phosphate (SH7P) via a transketolase reaction. The C3 unit, which combines with the C5 unit, is likely contributed from a suitable donor molecule such as SH7P via a transaldolase reaction. Dependent upon the origin of the C3-unit donor, this unit may consist either of an intact C3 unit or a C2 unit combined with a C1 unit. The octase produced from condensation of a C5 unit and a C3 unit can then be converted by unexceptional means to MTL. © 1984 American Chemical Society.