2-ニトロソ-9H-フルオレン

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

[MUTATION RESEARCH 87: 211 (1981)] DNA REPAIR DEFICIENT BACTERIAL TESTS: POSITIVE.

... NITROSOFLUORENE ... IS A POWERFUL FRAME SHIFT MUTAGEN IN SALMONELLA TYPHIMURIUM. THERE IS ... THOUGHT TO BE A CORRELATION BETWEEN CMPD THAT ARE MUTAGENIC FOR BACTERIA & THOSE WHICH ARE DIRECTLY CARCINOGENIC FOR ANIMALS. ... 2-NITROSOFLUORENE IS ONLY WEAKLY CARCINOGENIC. ITS MUTAGENICITY COULD BE CAUSED BY ABILITY OF BACTERIA TO REDUCE THE CMPD TO N-HYDROXY FLUORENAMINE ... THE INCREASED MUTAGENIC ACTIVITY OF THE NITROSO CMPD OVER THE N-HYDROXY DERIVATIVE MAY BE CAUSED BY INCR LIPID SOLUBILITY.

2-NITROSOFLUORENE SC INJECTED INTO RATS SHOWED LOCAL & EAR DUCT TUMORS. /FROM TABLE/

THE GROWTH TEMPERATURE OF SALMONELLA TYPHIMURIUM INFLUENCES THE EXTENT OF BINDING OF 2-NITROSOFLUORENE (NOF) TO THIS BACTERIUM AS WELL AS THE MUTAGENICITY OF THIS CARCINOGEN. (14)C-LABELED NOF UPTAKE IN BACTERIA GROWN AT DIFFERENT TEMPERATURES SHOWED GOOD CORRELATION WITH MUTAGENICITY DATA. THE AMOUNT OF NITROXYL FREE RADICAL ADDUCT FORMED DID NOT CORRELATE WITH UNSATURATED FATTY-ACID CONTENT.

2-NITROSOFLUORENE INDUCES FRAMESHIFT MUTATION & BASE-PAIR SUBSTITUTIONS IN SALMONELLA TYPHIMURIUM STRAINS TA98, TA100, TA1537 & TA1538. A COMPARISON OF THE MUTAGENIC POTENCY OF SEVERAL DERIVATIVES OF FLUORENE FOR SEVERAL STRAINS OF SALMONELLA TYPHIMURIUM SUGGEST THE IMPORTANCE OF A CARBONYL GROUP SUBSTITUTED AT THE CARBON-9 POSITION OF THE MUTAGENIC DERIVATIVE WITH RESPECT TO MUTAGENIC POTENCY. A FEASIBLE MECHANISM FOR THE INTERACTION OF MUTAGENIC FLUORENE DERIVATIVE WITH DNA IS PRESENTED. THIS MECHANISM REQUIRES THE INTERACTION OF THE MUTAGENIC MOLECULE WITH CARBON-8 OF QUANINE & A 2ND CONCURRENT INTERACTION WITH THE CARBON-4 AMINO GROUP OF AN ADJACENT CYTOSINE RESIDUE.

N-HYDROXY DERIVATIVES /OF AROMATIC AMINES/ CAN BE FORMED BY REDUCTION. WITHIN TISSUES ... ARE ... REDUCTASES ... WHICH REDUCE ... NITROSO ... GROUPS TO N-HYDROXY DERIVATIVES. ... 2-NITROSOFLUORENE, AN OXIDN PRODUCT OF N-HYDROXY-2-FLUORENAMINE, CAN BE CONVERTED BACK TO PARENT CMPD ENZYMATICALLY. HAMSTER & RABBIT LIVER SOL ENZYMES HAD CONSIDERABLY MORE ACTIVITY IN CARRYING OUT THIS REDUCTION THAN THOSE FROM THE RAT.

STUDIES OF NONENZYMIC REACTIONS OF TRANS-4-NITROSOSTILBENE, 4-NITROSOBIBENZYL, 2-NITROSOFLUORENE & P-NITROSOTOLUENE WITH GLUTATHIONE REVEALED THE CORRESPONDING HYDROXYLAMINE, AMINE & WATER-SOL ADDUCT, WHICH HYDROLYZED UNDER ACIDIC OR ALKALINE CONDITIONS TO AMINE & GLUTATHIONE SULFINIC ACID. REDUCTION TO THE AMINE IS EXPLAINED BY FORMATION OF ADDUCTS WHICH ARE REDUCED BY GLUTATHIONE WITH THE PRODUCTION OF OXIDIZED GLUTATHIONE.

THE CARCINOGEN 2-NITROSOFLUORENE REACTED WITH LIPID MOLECULES CONTAINING CARBON-CARBON DOUBLE BONDS TO YIELD FREE RADICALS (NITROXYL FREE RADICAL OF 2-NITROSOFLUORENE COVALENTLY BOUND TO THE LIPID).