Detail of "653-63-4"

Reference

Degradation of nucleic acids with ozone

Degradation of nucleic acids with ozone. VI. Labilization of the double-helical structure of calf thymus deoxyribonucleic acid. Shinriki, Nariko; Ishizaki, Kozo; Sato, Shoko; Miura, Kazunobu; Sawadaishi, Kazuyuki; Ueda, Tohru (Gov. Ind. Dev. Lab., Sapporo 061-01, Japan). Chem. Pharm. Bull., 32(9), 3636-40 (English) 1984. CODEN: CPBTAL. ISSN: 0009-2363. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) The degrdn. of calf thymus DNA (0.54 mg/mL) with O3 contg. O gas (O3 content, 0.1 mg/L; flow rate, 70 mL/min) was examd. The degrdn. rates of the 4 nucleotides in native and heat-denatured DNAs were in the following order: dGMP [902-04-5] x dTMP [365-07-1] > dCMP [1032-65-1] x dAMP [653-63-4] and dTMP > dGMP > dCMP x dAMP, resp. In the case of heat-denatured DNA, the rapid degrdn. of the thymine moiety seems to be due to its relatively weak stacking ability, so that it is more exposed to attack. In intact DNA, the double-helical structure of DNA tends to protect the base moieties from attack by O3. At the early stage of ozonization of native DNA, strand scission did not occur but the degrdn. of several guanine and/or thymine moieties was detected. As the ozonization proceeded, strand scissions of DNA and susceptibility to nuclease [9026-81-7] S1 digestion were obsd. Therefore, a specific O3 denaturation or labilization occurred, causing the double-helical structure to become increasingly loose due to the destruction of guanine and/or thymine moieties, and making the structure more accessible to nuclease S1.

In vitro binding of b-propiolactone to calf thymus DNA and mouse liver DNA to form 1-(2-carboxyethyl)adenine

In vitro binding of b-propiolactone to calf thymus DNA and mouse liver DNA to form 1-(2-carboxyethyl)adenine. Mate, Urszula; Solomon, Jerome J.; Segal, Alvin (Inst. Environ. Med., New York Univ. Sch. Med., New York, N. Y., USA). Chem.-Biol. Interact., 18(3), 327-36 (English) 1977. CODEN: CBINA8. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) In vitro reaction of b-propiolactone (I) [57-57-8] with calf thymus DNA and mouse liver DNA followed by acid (HCl) hydrolyses of the I-reacted DNA's resulted in the isolation of a new compd., 1-(2-carboxyethyl)adenine (1-CEA) [64920-12-3]. The structure was assigned on the basis of spectra at acidic, alk. and neutral pH and electron impact and chem. ionization mass spectra as well as chem. synthesis of 1-CEA from I and 2'-adenosine-5'-monophosphoric acid [653-63-4]. The only other compd. previously isolated from the in vitro and in vivo reactions of I and DNA was 7-(2-carboxyethyl)guanine (7-CEG) [1082-07-1] which was also identified as a product of the in vitro reaction. Under the conditions used the main product of alkylation was 1-CEA and the ratio of the concns. of 1-CEA to 7-CEG was ~3:1. The possible effect of the formation of 1-CEA on the structure of DNA and its role in chem. carcinogenesis is discussed.