Mechanisms of the in vitro antimutagenic action of chlorophyllin against benzo[a]pyrene: Studies of enzyme inhibition, molecular complex formation and degradation of the ultimate carcinogen

Chemopreventive properties of chlorophylls towards aflatoxin B1: a review of the antimutagenicity and anticarcinogenicity data in rainbow trout

“…By reducing the bioavailability of many genotoxins, these putative 'interceptor molecules' might represent an important first line of defense, perhaps rivaling such mechanisms as induction of detoxification enzymes or inhibition of carcinogen activating enzymes. In the period since the review by Hartman and Shankel was published, a number of papers has described the ability of CHL, chlorophylls, and other porphyrins to form molecular complexes with various carcinogens and mutagens in a manner consistent with the interceptor molecule hypothesis [8][9][10][11][12][13][14]. We will briefly review the evidence supporting the formation of a molecular complex between CHL and AFB 1 .…”

“…We will briefly review the evidence supporting the formation of a molecular complex between CHL and AFB 1 . However, the reader is referred to other work that describes the interactions formed between heterocyclic amines, polycyclic aromatic hydrocarbons, or a number of miscellaneous polycyclic planar mutagens and CHL, chlorophylls, or related porphyrins [8][9][10][11][12][13][14].…”

“…Computer modeling suggested that this was related to the electrostatic docking of charged carboxyl groups on CHL with the exocyclic amine on the mutagen [14]. However, the most important force stabilizing the complexes between CHL and most aromatic mutagens, including AFB 1 , involved the formation of numerous van der Waals interactions [11,12,14]. As shown in Fig.…”

Interactions of chlorophyllin with acridine orange, quinacrine mustard and doxorubicin analyzed by light absorption and fluorescence spectroscopy

“…It has frequently been reported during the past decade that CHL has strong anti-oxidative, antimutagenic and anti-carcinogenic properties [1]. Thus, the mutagenicity of such diverse agents as heterocyclic amines [2][3][4][5], aflatoxin B 1 [6,7], benzo[a]pyrene [8][9][10][11], dibenzo[a, 1]pyrene [12], doxorubicin [13], cyclophosphamide [14], reactive oxygen intermediates (ROIs) [15] or heavy metal ions [16][17][18], was shown to be reduced in the presence of CHL.…”

“…Another mechanism that has been advanced was based on the observation that CHL reacts directly with active groups of mutagens, resulting in their neutralization [19,22,23]. Still another mechanism to account for the antimutagenic property of CHL was explained by the formation of heterologous complexes with mutagens [3,4,9]. The latter mechanism was postulated based on the observation that CHL was most effective in reducing mutagenicity in the case of polycyclic compounds with flat aromatic structures [5,11,24].…”