Effect of molecular structure on the performance of triarylmethane dyes as therapeutic agents for photochemical purging of autologous bone marrow grafts from residual tumor cells

Indig, Guilherme L.; Andérson, Gregory S.; Nichols, Michael G.; Bartlett, Jeremy A.; Mellon, William S.; Sieber, Fritz

doi:10.1002/(sici)1520-6017(200001)89:1<88::aid-jps9>3.3.co;2-b

Cited by 24 publications

(39 citation statements)

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“…8,9 For example, Malachite green (MG, 4-[(4-dimethylaminophenyl)-phenylmethyl]-N,N-dimethylaniline)-a TAM + molecule-is used primarily as a dye in the textile industry; it is also useful in treating fungal and bacterial infections in fish and fish eggs. Although it has been prohibited for use to control fungal infections in commercial fisheries, 10,11 MG continues to be used worldwide because of its ready accessibility and low cost.…”

Section: -7mentioning

confidence: 99%

Unsymmetrically Substituted Leuco-Triarylmethane Molecules Formed from the Reaction of a Fischer's Base and α,β-Unsaturated Iminium Salts via a Michael-Type Reaction

Keum¹,

Kim²,

Kim³

2013

Bulletin of the Korean Chemical Society

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Section: -7mentioning

confidence: 99%

Unsymmetrically Substituted Leuco-Triarylmethane Molecules Formed from the Reaction of a Fischer's Base and α,β-Unsaturated Iminium Salts via a Michael-Type Reaction

Keum¹,

Kim²,

Kim³

2013

Bulletin of the Korean Chemical Society

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“…TPLSM of mitochondrial NAD(P)H has been used previously to indicate the metabolic status of living cells (11)(12)(13)(14)(15)(16). Figure 2 shows the effects of mitochondrial inhibitors and uncouplers on the intrinsic NAD(P)H fluorescence of RBL cells.…”

Section: Metabolic Imaging By Tplsm Of Nad(p)hmentioning

confidence: 99%

“…Two-photon metabolic imaging of the hippocampus (11), pancreas (12), intact cornea (13) and heart (14) has already been demonstrated successfully. It is also possible to simultaneously excite NAD(P)H and a variety of photosensitive drugs, which target mitochondria, to observe the effect of the drug on mitochondrial function (15,16).…”

mentioning

confidence: 99%

Reduction in DNA Synthesis During Two-photon Microscopy of Intrinsic Reduced Nicotinamide Adenine Dinucleotide Fluorescence¶

Nichols¹,

Barth²,

Nichols³

2005

Photochem Photobiol

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Two-photon laser scanning microscopy (TPLSM) of endogenous reduced nicotinamide adenine dinucleotide (NAD(P)H) provides important information regarding the cellular metabolic state. When imaging the punctate mitochondrial fluorescence originating from NAD(P)H in a rat basophilic leukemia (RBL) cell at low laser powers, no morphological changes are evident, and photobleaching is not observed when many images are taken. At higher powers, mitochondrial NAD(P)H fluorescence bleaches rapidly. To assess the limitations of this technique and to quantify the extent of photodamage, we have measured the effect of TPLSM on DNA synthesis. Although previous reports have indicated a threshold power for ''safe'' two-photon imaging, we find the laser power to be an insufficient indicator of photodamage. A more meaningful metric is a two-photon-absorbed dose that is proportional to the number of absorbed photon pairs. A temporary reduction of DNA synthesis in RBL cells occurs whenever a threshold dose of approximately 2 3 10 53 photon 2 cm 24 s 21 is exceeded. This threshold is independent of laser intensity when imaging with average powers ranging from 5 to 17 mW at 740 nm. Beyond this threshold, the extent of the reduction is intensity dependent. DNA synthesis returns to control levels after a recovery period of several hours.

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“…5,6 These dyes are also used in medicinal applications such as photochemotheraphy agents, particularly in eye protection devices etc. 7,8 The group of triarylmethane (TAM + ) dyes includes a wide range of substances with an absorption maxima between 450 and 650 nm. A number of TAM + dye molecules, such as Malachite green (MG), Crystal violet, Pararosanilin, etc., are well known.…”

Section: Introductionmentioning

confidence: 99%

X-ray Crystal Structure of Hetaryl Leuco-TAM Dyes, (2Z,2'E)-2,2'-(2-Phenyl Propane-1,3-diylidene) Bis(1,3,3-trimethyl indoline) Derivatives

2009

Bulletin of the Korean Chemical Society

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The unequivocal solid-state structure and stereochemistry of the hetaryl leuco-TAM dye, 2,2'-(2-phenyl propane-1,3-diylidene) bis(1,3,3-trimethylindoline) derivatives were established using X-ray single crystal analysis. The X-ray crystal analysis showed that the (Z, E)-isomers only formed stereoselectively, with a so-called "threebladed propeller" conformation, from the reaction of a Fischer base and benzaldehyde derivatives. These isomers were stacked in a juxtaposition to form a dimer or a double dimer, adopting either a triclinic, with P-1, or monoclinic crystal system with a space group P21/n in the unit cell of the crystal.

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Effect of molecular structure on the performance of triarylmethane dyes as therapeutic agents for photochemical purging of autologous bone marrow grafts from residual tumor cells

Cited by 24 publications

References 0 publications

Unsymmetrically Substituted Leuco-Triarylmethane Molecules Formed from the Reaction of a Fischer's Base and α,β-Unsaturated Iminium Salts via a Michael-Type Reaction

Unsymmetrically Substituted Leuco-Triarylmethane Molecules Formed from the Reaction of a Fischer's Base and α,β-Unsaturated Iminium Salts via a Michael-Type Reaction

Reduction in DNA Synthesis During Two-photon Microscopy of Intrinsic Reduced Nicotinamide Adenine Dinucleotide Fluorescence¶

X-ray Crystal Structure of Hetaryl Leuco-TAM Dyes, (2Z,2'E)-2,2'-(2-Phenyl Propane-1,3-diylidene) Bis(1,3,3-trimethyl indoline) Derivatives

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