Urakami T, Tanaka A, Yamaguchi K, Tsuji T, Niki E
Biochemicals Division, Mitsubishi Gas Chemical Co., Tokyo, Japan.
Biofactors. 1995;5(3):139-46.
Esters of pyrroloquinoline quinone (PQQ), a cofactor of microbial quinoprotein enzyme, and imidazopyrroloquinoline (IPQ, from PQQ and glycine) were synthesized, and their chemical stability, toxicity to L-M cells and nerve growth factor (NGF) inducing activity in L-M cells were studied. PQQ esters were found to be potent enhancers of NGF production, but IPQ esters had only marginal effects on NGF production. The monoester of PQQ with a methoxycarbonyl group at C-2 of PQQ is a most effective compound because of its NGF inducing activity, limited toxicity, safety and chemical stability. These results suggest that PQQ-2-esters could be developed as a curative or preventive drug for retrograde neural diseases in the central and perpheral nervous system.
合成了微生物醌蛋白酶的辅因子吡咯并喹啉醌（PQQ）的酯以及咪唑并吡咯并喹啉（IPQ，由PQQ和甘氨酸合成），并研究了它们的化学稳定性、对L-M细胞的毒性以及在L-M细胞中诱导神经生长因子（NGF）的活性。发现PQQ酯是NGF产生的有效增强剂，但IPQ酯对NGF产生只有微弱影响。PQQ在C-2位带有甲氧基羰基的单酯是一种最有效的化合物，因为它具有诱导NGF的活性、有限的毒性、安全性和化学稳定性。这些结果表明，PQQ-2-酯可开发成为中枢和外周神经系统逆行性神经疾病的治疗或预防药物。
